Develop a Strategy for Midlife Bachelor Success

If you want to get out there and date successfully as a midlife bachelor, you will need a well-thought-out strategy – and that is what this section is all about. Earlier in the Some Fundamental Truths about Women and Midlife Dating Today section, we talked essentially about today’s midlife dating landscape … including some behavioral basics and many general and specific observations about women from a midlife bachelor perspective, etc. The Fundamental Truths section explained what you would be dealing with … what you can expect to find out there … that is what I mean by the “landscape.”

In the Midlife Bachelor Personal Makeover section, we focused more on YOU as a midlife bachelor … and how to manage many personal things that might seem obvious to some but are often overlooked by many of our midlife bachelor brothers. I’m talking about your appearance details … and the basics of your overall attitude, what comes out of your mouth, how you present yourself, etc.

Before you can begin to come up with your midlife bachelor strategy, you must first have a good handle on everything I’ve discussed thus far in those earlier sections (Fundamental Truths and the Midlife Bachelor Personal Makeover) … as they are the backdrop or stage or platform from which you need to launch your strategy. A rocket needs a launchpad to lift off, right? An actor needs a step to perform, correct? So do you, as a midlife bachelor, need this foundation of knowledge – as it is all part of your launchpad, your stage. Hopefully, this makes sense to you.

Armed with your foundation of knowledge, you can now think about defining a well-thought-out and carefully planned midlife bachelor strategy that is unique to your situation. A good midlife bachelor strategy includes many inputs (in addition to those from the other sections of this site I mentioned above). First, you need to understand who you are and your short-term and long-term dating objectives. Hopefully, you should have an idea about the type of woman you are seeking … maybe not what she looks like per se, but at least the kind of personality traits or interests she might have.

You need to understand all of the various personal and technological resources you have at your disposal and how to use them successfully. And you’ve got to be aware of your strengths and weaknesses so that you can either use them or minimize them to maximize your chances of success. Finally, no successful strategy can be static – it has to be evolutionary … reactive, and adaptive to a changing midlife bachelor landscape.

This means that you have to periodically reassess each aspect of your strategy, leverage what seems to be working the best, and modify what’s not working out well. This section aims to help you figure out your plan for midlife bachelor success … and to help establish a mindset of continuously learning from yourself and re-optimizing your behavior.

Step 1:  Set your short-term & long-term dating objectives

Before you can start to create a midlife bachelor strategy, you first have to understand yourself well enough to know what your midlife dating objectives could or should be.  I’m about to give you some things to consider – which should help guide your mindset and lead you toward the ability to set some reasonable and attainable personal dating objectives that constitute the first element of an overall strategy. The more you think everything through, the less likely you will be to make decisions that are counterproductive for you in the long run… so please keep that in mind.   And by the way, what I’m about to discuss does not constitute all possible inputs for determining short- and long-term dating objectives – they are just some of the more common issues that I have noticed either concerning myself, or concerning people I know.   Remember – you can learn just as much from watching others as you can from protecting yourself.

How long have you been single?

Much can depend on how long you have been single in terms of goal setting and establishing an overall midlife bachelor strategy.  You have to carefully consider where you are concerning your own “relationship readiness,” … which is a product of your history and that history’s effect on your current mindset.   You’ve got to factor all of this into the goals you set and the strategy you establish for yourself to keep everything realistic.   Your past strongly influences your current state of mind, and often the more recent that something significant has occurred, the stronger the influence it will have upon you.   Here are a few examples of how long someone has been single and what kind of mindset might result.

If you are a brand-new midlife bachelor who has just come out of a very long relationship, it can be challenging to know with confidence what path is best for you to take in terms of dating.   A lot can depend on YOUR ATTITUDE, which is likely influenced by that last long-term relationship – and that influence might be positive or negative.   For example, if your previous long-term relationship was a continuous living hell, you likely have some personal issues to deal with before you lly date successfully.   You would have to realize that all women are not like your ex, and part of your strategy needs to be to continuously check yourself to ensure that you don’t treat women like you would your ex.   In other words, if you are fresh out of a long-term living hell relationship, be mindful not to project the poor qualities of your ex onto whatever woman you might find yourself with.    If your ex cheated on you, don’t assume or presume that your next girlfriend will cheat on you.

Here’s a different scenario to consider – again, let’s assume you are a brand-new midlife bachelor … but this time, you are now suddenly single because your wife (who you loved so dearly) suddenly passed away.   [I know this is morbid, but bear with me.]   In the previous “living hell relationship” example, I suggested that you be mindful not to project the negative qualities of your ex onto a new girlfriend or potential girlfriend.

Here I’ll say something similar – but not necessarily in a negative sense.   The love of your life just left you (through death) … you don’t want to project her qualities (good or bad) onto anyone new.  In an example case, you always want to feel the ability to treat each woman individually without prejudice … you want her to be able to stand with you on her own merits.   Why do I mention this here … when supposedly discussing “How long have you been single”?

Because the more recent your midlife bachelorhood began, the more likely you are to be overly influenced by your past and the more mistake-prone you will be.  Many such mistakes involve the presumption or projection of the qualities of your last relationship onto a new partner or potential partner.   Simple recognition of this fact is my point to you right now.

Let’s also consider an opposite example of midlife bachelorhood.  Let us say that you are in your mid-forties and have never been married.  Let’s also say that you have extreme difficulty getting a date, much less a girlfriend.  In other words, you are not “suddenly” a midlife bachelor but instead, you are “perpetually” a midlife bachelor.  In a case like this, sly have some problem or problems – and your first priority should be to try to recognize what it or they are so that you can start to cope. I know several guys in this exact situation … some might even argue that I, myself, fit this profile.

You have to examine yourself very closely,  … possibly seek out some comments from your friends … maybe even (oh no) consider what some of your prior girlfriends have told you about yourself.  Traits you may have that I’m thinking of might include things like “self-absorbed”, “domineering,” “controlling,” “manipulative”, “unreliable,” and maybe “crap”, “racist”.  You get the idea – perhaps you are a bad apple and need a major personality overhaul.   [If any of these are the case, don’t feel isolated … as several of those words have been used to describe me.   You are not alone, my brother.]  My point here – especially if you have been a bachelor for an extended period of time, recognize and accept that part of your strategy and goal-setting will need to include how you overcome the personal challenges that make up your current personality.  This is true for every one of us – not just perpetual bachelors … but the perpetual bachelor should put self-examination and modification at the top of his priority list.

Each of the three just-described examples describes how you’ve come to be a midlife bachelor … with the first two cases being rather sudden.    In all cases, we learned that the more recent you’ve become a bachelor, the more error-prone you are … and that (no matter who you are) your goals need to include how to overcome your own personal challenges. In terms of setting your short-term and long-term dating objectives, you need to allow yourself enough time to work through your unique issues.   This could mean a short-term dating strategy of not getting involved with someone extremely quickly … or it could mean not dating at all for a wile just focusing on sharpening your social skills with various female friends.

Usually the worst short-term dating strategy for a brand-new midlife bachelor is to get seriously involved with the first woman you date a concisehort amount of time … as that is essentially a rebound scenario and is often doomed in long run. [I’ll discuss “rebound” in depth later in this section.]   To be clear, the bottom-line recommendation I have for you as a midlife bachelor to consider with respect to the length of time you’ve been single is – whether or not in the long-term you want to be in a serious relationship, take the time necessary in the short-term to understand and deal with any issues you have with respect to yourself, to women, or to the world at large.

Do you want to stay single?

I just finished discussing the role the length of time someone has been single can play in terms of determining one’s dating objectives, and how important it is for everyone to take the necessary time to cope … and how that can especially impact one’s short-term dating objectives and strategy.    The next question to ask yourself is – do you want to stay single, or do you ultimately want to be in a relationship?  Your personal answer to this question is critical – as it will significantly influence your goals and your behavior.   Plus this may not be the easiest question for you to answer – at least right now.

Some people know in their heart that they need to be in a relationship – as otherwise they feel lost, or feel that their lives have no meaning.  Other people don’t really need anyone, and a relationship is optional to them.  Still others believe that women are parasitic by nature, and should never be taken too seriously … and so a relationship is out of the question.   Sometimes being single is required by one’s situation in life – maybe you are a single father, and have full-time custody of your four young children … so how on earth would you have time to date anyone (whether you want to be single or not)?

For many brand-new midlife bachelors – it might be best to put off answering the question about whether you want to stay single until you have reached a better understanding of yourself, and your particular emotional issues.   There is nothing wrong with delaying such a decision for six months or a year or more than a year – if that is what you feel allows you the time you need to reset yourself, and establish your own personal equilibrium with the world at large given your new bachelor situation.

If you are the new midlife bachelor with full-time custody of four young children, you might need an even lengthier period of time to adjust yourself.   Whatever your situation, there is no magic formula to use for the length of time required for you adjust to the newness of midlife bachelorhood – there is no rule of thumb.   It is all unique to each of us.   The best I can tell you is that you will know in your heart what is right for you with respect to wanting (or not wanting) to stay single.   Just be sure to avoid the rebound scenario (fear of being single) is not what guides your answer.

Are you better off being single?

Many midlife bachelors probably are better off being single – at least for a year or two.   As I’ve mentioned, each of us needs to go through the phase where we recognize and address our own unique challenges, and also decide for ourselves what is best in both the near-term and the longer-term with respect to our desire for a relationship.   Many of us really need time to get over the pain of our last long-term relationship so that we minimize the future effects of our own emotional baggage.  Sometimes this baggage has taken years to accumulate – and our behavior and habits have become so ingrained within us that it may take more time than one would guess to get past it.   How much time?   Well more than six months – most certainly.   What is the later boundary?  That’s hard to quantify in general terms because so much depends upon you and your unique issues.   My main message to you – the brand-new midlife bachelor is … you are better off staying single for some period of time, but probably not forever.  If you are not a brand-new midlife bachelor, but have been one for several years and are still not experiencing success in terms of obtaining and/or retaining a suitable girlfriend – then you may need to pause temporarily from your pursuit of women to examine yourself, and figure out what adjustments you need to make in order for you to become a better boyfriend, or even just a more attractive person overall.  Knowing where you are at with respect to the question “are you better off being single?” will be a key input into the establishment of both your short-term and long-term dating objectives

Rebound – Does fear of being single drive your behavior?  

This whole discussion concerning the notion of “rebound” behavior is critical because I’ve seen it happen so often.  Hell – it has driven my own behavior countless times in the past so I am extremely familiar with it on a personal level!  As you work to establish your short- and long-term dating objectives, you need to be certain that “fear of being single” does not overly influence the goals you set for yourself.   “Fear of being single” is essentially the key characteristic of someone who is on the rebound – and making any sort of decisions or goals based on fear is likely to lead to mistakes.   So how do you know if you are “on the rebound”, or if “fear of being single” is what drives you?   The pre-qualification is, of course, that you just got out of a long-term relationship … and then most or all of the following are true about you:

  1. Your friends give you the nickname “Rebound”.
  2. You become instantly enamored with any woman who pays even a little attention to you.
  3. You ignore obvious major flaws in a woman that you want to date.
  4. You feel overwhelmingly alone at all times.
  5. You will do just about anything to get a date, any date.

Your friends give you the nickname “Rebound”.

Sometimes people are so obviously on the rebound that this label becomes automatic.   Consider my friend, James – whose wife had an affair on him after ten years of marriage.  They subsequently parted ways, and James was like a lost puppy in the world – not knowing who loves him [“lost puppy syndrome”]. He absolutely HAD to have a woman in his life, and he was looking for a woman everywhere he went.   Not that he was a perpetual scammer – don’t get me wrong here.

Rather he looked at every woman like a puppy would … attention would really get him interested quickly (even if the attention was innocent).  [I call this “puppy syndrome”.]   All of these traits were so obvious with James that I called him the nickname “Rebound” – which he didn’t necessarily appreciate at the time, but it was so accurate!  When he used to get mad at me for calling him that or introducing him that way, I would tell him privately that he should just embrace reality, and go with it.

You become instantly enamored with any woman who pays even a little attention to you.

I just explained how my friend, James, so obviously and constantly exhibited “puppy syndrome” … where any woman who was nice to him became a target for his love.  I’m talking ANY woman here – waitresses who were good at their job would be misinterpreted by him … women who worked retail and were especially helpful or friendly … basically any woman he came into contact with was deemed a dating candidate if she said anything even remotely nice to him.  There were several occasions where I reminded James that sometimes women are just nice people, or behave nicely because it is part of their job.   Often times, guys who are in a rebound mode will fall in love several times each day.   Best to keep those rose-colored glasses in your pocket.

You ignore obvious major flaws in a woman that you want to date.

Probably the best single “rebound” characteristic that my friend, James, displayed at the time was when James fell in love with a stripper at a local strip club.  First recognize that James is this extremely conservative guy who although not religious is easily lumped into the category of being one of the pillars of his community.  We are talking school volunteer, great father to his two young children, decent, kind, intelligent, educated, etc.

With that as a backdrop, imagine him going into a strip club alone after his wife left him.  Imagine what an easy target he was for the strippers in that club.  The guy made a lot of money at the time, and was eager to absorb any attention from any woman … so of course the smartest stripper would figure this out, and encourage him to come back and see her.  I remember James telling me at the time, “Dude – I think this stripper at the <censored> club wants to go out with me … she is so nice to me.  And Dude – she is so hot, and she keeps telling me she wants to see me more.”   You get the idea.  I remember telling him at the time, “James – she’s a stripper!  Of course she wants you to come back … because you keep feeding her $100 bills!”   He eventually figured this all out – but it took him a month or two.

I’m not sure if he ever asked her out and didn’t tell me – but he did stop talking about her rather suddenly.  A woman who is a stripper has an obvious flaw – she gets paid for showing her body to men … or worse!   This is an extreme example, but someone in a rebound state of mind will look past the obvious.

You feel overwhelmingly alone at all times.

I’m kind of on a roll here with respect to my friend, James – so I’ll continue using him as an example.   After James became suddenly single, he could not stand to be alone.  He had his two young children three days each week – and was occupied those days.  But on the days and nights that he did not have his kids, one would think that he might need some down time?  No way – he had what I would call paranoid tendencies … especially at first.  He just didn’t want to be alone – it was like he was afraid to be alone.  Now at the time I sympathized with the guy quite a bit, and went out of my way to do things with him.  [Plus he was fun to do things with because he was always looking at all the women as dating targets all the time … which I found extremely entertaining.]  The point I am making here is – that if you recently got out of a relationship, and feel so alone that getting a date seems obsessive … then you are exhibiting a sign of being on the rebound.

You will do just about anything to get a date, any date

This describes the sum of all of the characteristics of being on the rebound that I’ve described so far.  My dear friend, James, was the most extreme example to me of these.  It might help you to know that time heals things – and that James ultimately calmed down, and settled into a permanent relationship.   I, myself, have been on the rebound plenty of times in my life – and I’ve exhibited many of the same traits that James did – but each of us have different degrees of rebound behavior that make up our respective personalities.   So although you may not find yourself going to the extremes that I described James as going through – you might still be on the rebound if even a hint of such behavior applies to you.

This whole discussion about being on the rebound is meant to make you cognizant of what can be driving your thought patterns at this particular midlife bachelor point of your life.  In order to effectively set realistic short- and long-term dating objectives, you have to understand yourself well enough to know what may be exerting undue influence on the way you think … simply because of the time proximity to your last relationship.   Being on the rebound is fine – you can have a lot of fun with it.  Letting rebound behavior determine your long-term future, however, may not be in your best interest … so keep all of this in mind.

Understanding your current needs versus your longer-term needs.   So far I’ve talked about a number of different inputs to the thought process that goes into establishing your dating objectives.  How long you’ve been single plays a large role in determining your true mental readiness to pursue a real relationship.  I’ve also asked you to think about whether you want to stay single, and also whether you are better off being single … although you should recognize that your answers to those particular questions might change over time.  I also exposed the notion of rebound behavior – which is common in the newest of midlife bachelors … who pursue women out of fear of being single.   All of the aforementioned are things you should be thinking about … how they apply to you, and how your own self-judgment might be influenced by these various factors.   I can guide you through some of these and other influences – but you have to be the one to have a level head, and make the final call about what affects you the most, and the best way for you as an individual to proceed.

With everything I’ve just said, think about what you feel your needs are.  You have current needs, and you have longer-term needs, right?  If you are a brand-new midlife bachelor, your current needs might just be to get a damn date … any date.   And there is nothing wrong with that.   Just keep it all in perspective.  In other words, in the shorter-term try to focus on how to meet women and how to ask them out on a date … how to go out on a date … how to act on a date (maybe how NOT to act on a date) … where to go on a date, etc.  A good short-term objective for any newer midlife bachelor is simply “dating”.  Note that “dating” is different than the rebound scenario I described earlier … where my buddy, James, was on a relentless pursuit of all women within an eye-shot.  In other words, don’t be relentless and pursue everything in sight … instead choose wisely.  Think rifle shot (not shotgun).

While in the short-term a casual dating strategy might be best for you to pursue, in the long-run many of us know in our hearts that we need a relationship … and it is perfectly fine and normal to have that as your longer-term goal.  You just don’t want to rush into such a relationship … especially if you are fresh out of the gates as a midlife bachelor.  Most of us should give casual dating a try for a while before pursuing something long-term.   You should try hanging out with different types of women to see which one is the kind you think you could stay with for a long period of time.

You should also be aware of the various Types of Women I described in the section entitled Some Fundamental Truths about Women and Midlife Dating Today … keeping in mind that most women won’t show their true colors for some number of months.  But they eventually do, and then you can with certainty place them into one or more of the categories I described.  As time goes on, it will get easier for you – you will know what type of women are compatible … truly compatible with you.   And I don’t necessarily just mean the ones with big tits, although those are certainly a major bonus.

Define your objectives.

With everything I’ve just given you to think about, your head must be spinning.  There is a lot to keep in mind.  There are so many possible inputs and influences that can impact the short- and long-term dating objectives that you are about to set for yourself.  How can you possibly pull it all together and know that you are making the right choices?   The best way is for you to take a look at the following chart that shows the Midlife Bachelor Objective Roadmap, and see where you personally are at.   The left side of the chart shows the steps every midlife bachelor must take in order to get through the various hurdles of being a new bachelor, and ultimately wind up being successful at having a long-term relationship.   The right side shows ROUGHLY when these milestones might be achieved time-wise into your bachelorhood.

Midlife Bachelor Objective Roadmap

                                Objective ————— Rough Bachelor Timeline

strategy clip image001

When you are a brand-new midlife bachelor, you pretty much have to start at the very top and progressively work your way down through the various milestones.  You cannot skip any of the steps – nor can you rush your way through it all … lest you have to start over.  [For example, if you have been a brand-new midlife bachelor fresh out of a 10+ year marriage … and hook up with a woman after three months, and decide that “she’s it”, “the one”, “your next wife”, then you have fallen victim to the rebound scenario, and should be prepared for reality to catch up with you.  [When that happens, please start again at the top of the chart.]

As outlined in this and previous sections, all midlife bachelors have to start with the basics – your personal appearance.  Next work on your attitude and social skills … while focusing on keeping your past in your past.  You’ll then need to focus on getting a date and going on dates, until you can experience success at both … which means actually getting dates AND having fun on those dates.  Finally, as you mature through midlife bachelorhood – you’ll get to the point that not just any date will do.  Now you can focus on dating a woman who you really want to go out with (which we’ll discuss shortly).  Once you can do that, you are probably ready for your next long-term relationship.   And after you are seriously involved with someone you love – that is when you can consider your midlife bachelorhood a thing of the past (regardless of whether you actually get married or not).

Notice in the chart that the “perpetual bachelor” is placed right up with the brand-new midlife bachelor.  The reason for doing so is that perpetual bachelors have one or more issues that prevent them from succeeding … and they really need to admit to themselves that they need to start at square one.  [In fairness, ALL midlife bachelors need to make sure they address each of the steps … so really everyone begins at the beginning.]

I’m not necessarily saying that all midlife bachelors (perpetual or otherwise) have personal appearance or hygiene challenges – but I am saying that regardless of who you are, it makes a lot of sense to take a good overall look at yourself … and pay particular attention to many of the details that I call out.   You’ve perhaps heard the expression “the devil is in the details”?  That is precisely what I’m talking about.   You could be the nicest guy in the whole world – but if your teeth are jacked up, then who is going to want to kiss you?   Or maybe you are the best-looking guy around – but the trash you talk makes you unattractive to all after the first ten minutes of conversation with you.   You get the idea – no one is perfect, and everyone can benefit if you optimize the totality of yourself for success as a midlife bachelor.

Step 2:  Conquer the Basics and Start Dating

Okay – so at Step 1, we figured out at least roughly whether we ultimately want to be in a relationship and (if so) what the various midlife bachelor developmental stages are in order to achieve that type of success.   We started with the basics (personal appearance and hygiene, then moved on to attitude and social skills development while minimizing one’s individual emotional baggage, then we somehow magically moved on to getting a date (ANY date), and began to work on the ability to have fun on those dates.   This magical transition from working on your personal basics to “developmental dating” is what Step 2 is all about.

Developmental Dating
What I call “developmental dating” refers to your ability as a midlife bachelor to go out, and get a date with a woman … go out on that date … and actually have fun on the date.   “Having fun on the date” does not necessarily equate with “having sex” – but it might.   Let’s face it – as men, sex is always our goal no matter what.   But – when you first start dating, if you are sincere about successfully re-entering the dating world as a midlife bachelor, then your focus should be foremost on having a nice time on any given date.  A “nice time” always means that the date was a pleasant, comfortable experience for all involved.

A “nice time” might sometimes mean that you are able to get yourself a good night kiss – although not always.   A “nice time” might mean that you learned a lot about one another, and want to know more.  A “nice time” might mean that she won’t press charges (just joking).   A “nice time” can mean many things obviously – but it might NOT necessarily mean that you want to see one another again.   In other words, you can have a “nice time” with someone, and not want to date them.  Don’t pre-judge your success at developmental dating based on your initial ability or inability to get laid or kissed or get second dates, as dating success for a midlife bachelor is often more of an evolutionary (versus instantaneously) successful process.   I’ll explain all of this so that it is clear.

When you first re-enter the midlife dating world, two of the biggest obstacles are

  1. Getting a date
  2. Having fun on a date you do get

First Identify a Potential Date

Just asking for a date can be a stressful experience – especially if you have not been single for quite some time.   First you have to identify a woman who you want to ask out.  Now this is important – the woman has to like you and/or be attracted to you.   You cannot automatically assume (because of your ego) that every woman you are interested in will also be interested in you.   Unless you are super good-looking, there is always some element of random chance involved that she will (or will not) recognize some potential chemistry between the two of you.

Sometimes it is easy to know that a woman is attracted to you, and maybe wants to go out.  Some women are obvious – they go out of their way to either talk to you, or to notice you, or to say “hi” to you.  Other women are really hard to read – and you have to keep your eyes open at all times for any hint of a possibility of a woman’s interest.   Here are a couple of stories from my past concerning obvious and non-obvious women.   Margie (who I also wrote about earlier) worked at a local postal retail store where I rented a mailbox.   At that time, whenever I received a FEDEX or UPS package, the store would call me and ask me to come and pick it up.   When I was in the store, I always spoke to several of the employees there – but Margie was a little different … she would almost never look at me in the face.

She would instead look down or look away.   At the time I didn’t think too much about it – and I had not really considered Margie someone who would be interested in me or vice versa.   But over several months, I noticed that it was always Margie who was calling me from the store.   One day, she called and I asked if I had a package to pickup … and she said “no”.   I then asked her why she was calling … and she said she didn’t know, and sounded kind of embarrassed.   Fortunately, I immediately picked up on what was going on, and I asked her if she wanted to have dinner … and she got all excited, and said sure.   She later admitted to me that she had a huge crush on me … which I almost would not have noticed had she not called and embarrassed herself.   [She said that she did not expect me to answer my home phone, and was calling to hear my voice on the answering machine.]  Margie was really hard to read – even when we were dating, she had a hard time looking right at me.

Margie was really shy, and had I not busted her calling my home phone, I probably never would have recognized that she liked me.   A good midlife bachelor lesson is here – always keep your eyes open.   Don’t overly assume the best, but also don’t be ignorant of what may be going on.  If there is any question about a woman’s intentions about you, you can always talk to her more and try to figure out whether she is just a nice person versus interested in dating you.

Margie was very non-obvious prior to the phone calls.  Other women are way more obvious about liking you.  You may recall my earlier story about Becky, the blonde bombshell nymphomaniac who demonstrated to me that the hottest fires burn out the quickest?  I mentioned before that she and I had been “friends” for a long period of time – but now let me elaborate on that to illustrate how some women are OBVIOUS about liking you.

For many years, Becky had worked at a local pharmacy as a pharmacy technician – the person who interacts with the people who need to fill or refill a prescription.   I can remember in my mid-twenties seeing Becky at this pharmacy … and each of us would always say “hi” when I was in the store (whether I needed a prescription or not).   We would do the small talk thing – we would tell one another about who we were dating, how that was going, etc.   The point here is that she would go way out of her way to talk to me, and I would, too.  It was always a friendship thing because neither one of us were ever single at the same time over the years … until fairly recently.  After I was dating Becky, she told me what I essentially already knew … that for all those years, she wanted to go out with me.   Of course, my very physical relationship with Becky went nuclear (no survivors) very quickly – but hey, it was fun while it lasted!

Lead Generation – Finding New Women to Date

If you are like most guys, you probably h of base level of wowho you know already like you.  These are women who are somehow part of your daily or weekly busy routinee already aware that they are interested in you.  They are your “fan club”.   If you are outgoing and/or especially good-looking, you probably have a large fan club – and can start your dating adventure by picking from that pool of candidates.   However, if you had been married for a long-time – and/or if you have basically been a prick … then you may have a substantially smaller fan club, or possibly even no fan club to mine for dating candidates.

What do you do if you don’t have any women around who you want to go out with?  You take positive, proactive steps to generate new leads.  I use the term “leads” because I’ve been in sales for the past twenty years … and essentially “leads” are what bring you new business.   And new business is exactly what we are talking about for you, the midlife bachelor, who is short on women to date.

I say that you must take “positive, proactive steps” to generate new leads, to meet new women because it will take effort on your part.  You cannot sit at home on your couch in front of the television, and expect that women will somehow line up to meet you – that just doesn’t happen.   You may just have to break out of your comfort zone, and try new things in order to meet women.  One thing is certain – it will definitely be a significant positive personal growth experience for you.  Sure breaking out of your shell, and meeting new women will have its ups and downs.  You will experience success and failure.   Your roughest times will likely be at the beginning of your journey, but take heart that good times do await you!

Every rejection or failure makes you stronger and more knowledgeable.  If you try to meet a woman or attempt to strike up a conversation with her – and she completely blows you off, that is fine.  It is HER LOSS, not yours.   Maybe you didn’t see the wedding ring on her finger?  Maybe she was waiting for her boyfriend?  Maybe she is a lesbian?  Maybe she likes guys with tattoos and shaved heads?  Or maybe she is just a rude bitch?   Sometimes you will never know – but other times, you can later analyze a failed interaction and possibly figure out what you could have done differently.   Maybe you said something cheesy to her, and it sounded pathetic? Perhaps you looked nervous, and she thought you were some freak show?  Maybe you had a booger on your face?   When trying to figure out what lessons you’ve learned from a particular interaction, take a hard look at yourself.  Put yourself in the woman’s shoes, and try to envision things from her point of view.   Sometimes it helps to get the opinion of a female friend on stuff … sometimes you can even take a female friend with you as yowingman man”, and get her direct input on what you are doing or sayingOf course, not Not all of us have that luxue – so it might just be up to you to figure it outAll I can tell  is that practice makes perfect – and even though no two interactions with a new woman are the same, you will become more skilled from a conversation standpoint the more often you try.

Get Out and Be Seen
In order to meet new women, you’ve got to get out of the house and be seen.  This means doing things outside of work that expose you to the world.  It could mean going to the gym.  It could mean going to happy hour with existing or new friends once each week.  It could mean having coffee regularly at the local nearby coffee shop.  It could mean taking a class somewhere, or joining some sort of interest group.  It could mean volunteering somewhere.   Or it could mean all of these things – but it really depends on you, what kind of time you have on your hands, what personal interests you have, etc.  The bottom line is that you have to “go public” – see and be seen.  Women covet what they see – so they’ve got to see you in order to want to know more.

Always Say Something  – given that you have now “gone public”, and are out and about … you’ve got to focus on being outgoing, friendly, and approachable.   Try your best to always say something, anything to women.   It doesn’t hjust to be your target womenomen – you can be conversational will all women.  In fact, sometimes it helps to develop as many new friendships with women overall (even unavailable women) because it may lead to them wanting to introduce you to one of their single friends.  Plus you might just need the conversational practice, too.  In other words, when you are out in the world, you shouldn’t be hitting on all women all of the time (as that is cheesy) … many times just normal conversation is good.  I’ve found that the best bet is just to always say something … anything.  If you are standing in line for something, make an appropriate comment to the woman in front of you.   “Have you been standing here long?”  “I know this line moves really slowly – hope you are not in a hurry.”  “Are those boobs real?”  Okay – so I’m just kidding with the boob comment … you would NEVER want to say that!  Make sure whatever you say is reasonably friendly – and make sure that you have a happy look on your face … as you don’t want to scare anyone, right?

Use What You’ve Got.   Every single one of us knows what our strengths are out in the world – take advantage of your strengths.  For example – if dressing up is your thing, then use it strategically … be dressed up when you are out and about, as you may attract more women that way.  Plus you might unconsciously feel better about yourself, and somehow become just a little bit more charming.  If you are exceptionally good-looking, use that to your advantage … good looks can overcome many things like marginal conversation skills, for example.   If you are rich as hell – then use that to your advantage … maybe pay for everyone’s drinks, possibly drop a story or two about your recent European vacation, etc.   Whatever you do – don’t overblow it.   There is a fine line between exposing one’s strengths (like wealth) through carefully dialog versus embellishment or braggartism.   One of my very wealthy friends is a major braggart – constantly talking about himself … saying things like “I am building my mansion as a monument to myself”.  UGHHHH!    I love the guy, but I can only tolerate him for several hours before he really starts getting on my nerves.   Now some women might be fascinated with this type of bragging … but most of the women I have dated could not stand to listen to the guy.   My main message to you, the midlife bachelor, here is to exploit your personal strengths , and use them to your advantage.

Minimize Your Weaknesses.  Just as we each know what our strengths are, we also know our own respective weaknesses.   Keep those weaknesses hidden, or underexposed if at all possible – that way they are less likely to interfere with your success with women.   What kind of weaknesses?  There is a whole range of major and minor weaknesses that midlife bachelors have.   Here are several of mine.   An obvious one is golf.   I hate golf, and I never play it because I don’t have the patience for it.   So if I were to be invited to a singles golf excursion – would I go?  Hell no – I’d look like a complete idiot!  A more typical weakness I have is dancing – I have absolutely no rhythm whatsoever.  Not to say that I won’t go dancing … as heaven knows that if you get enough alcohol in me, I will hit the dance floor with the confidence of a professional.   But the way I dance is just wrong and awful – it just shouldn’t be done.  If I don’t receive any criticism about how I dance, then the woman I’m with is being very polite.  You get the idea – you know what your personal weaknesses are … sometimes you may be able to train yourself out of them … but in large part, when you are out there dating or attempting to meet new women, your best bet is to do everything possible to minimize your weaknesses.

Maximize Your Opportunities
As a midlife bachelor, part of “getting out and being seen” means maximizing all of your potential opportunities to meet new women.  You’ve heard me discuss all of this in previous sections, so hopefully it is obvious.  You need to:

  1. Plant seeds in the overall community of women .   This means being nice overall, and making new female friends wherever you go.  The idea is that if enough women know you are single, you will eventually be introduced to their single friends.
  2. Leverage your friendships .   Be proactive with respect to networking through your friendships.  Ask your friends about specific women they know – there really is no harm in this.  For example, one of my neighbors has this friend named Tracy who I briefly met while she was walking my neighbor’s dog.  I asked my neighbor a lot of questions about Tracy, and told her that I thought her friend was HOT STUFF.  Now I have not been single since I met Tracy – so I there is no opportunity for me to capitalize on this act of networking … but I’ve spoken to Tracy several times since all of this, and I can tell that she is interested in me.   All it would take is me being single, and asking her out once – that would be an instant hookup.
  3. Go on a Blind Date .   Wow – blind dates are risky, but if you are truly maximizing your opportunities, then you will entertain doing this.  There is an element of trust involved – and also just plain random luck.  But if you are planting your seeds [item 1)] and leveraging your friendships [item 2)], then at some point you will cross the blind date bridge – and you should go for it.   Why?  Because the golden rule of midlife bachelorhood is ALWAYS GO FOR IT!  Okay – there’s that golden rule PLUS you probably need the dating practice.   If your blind date turns out to be a no-go in terms of a dating partner, remember to be nice to her … and turn her into a friend.  That way you can at least possibly network through her, right?
  4. Pick the low-hanging fruit first .   As a midlife bachelor, you probably need any dating practice you can get … so date anyone you can in order to get some experience under your belt (ha ha).   In other words, date who you can at first – and use those experiences to “find your center” so that you become more in-tune with what you like and dislike in a woman, on a date, etc.   Part of maturing as a midlife bachelor involves graduating to the next level of “dating who you want” … but it might be best for you to learn your lessons while first dating someone/anyone more casually.

In the context of “lead generation”, you as a midlife bachelor need to do everything I’ve mentioned in order to maximize your own personal opportunities to meet new women.  None of what I’ve discussed necessarily comes easy.  In fact, it can be downright scary for those bachelors who were married for a very long period of time.  It might seem like a set of huge hurdles to overcome – but (just like anything else), if you break everything down into individual well-thought-out manageable steps, then you can really do it.  And you’ve got to try … because if you do not try, then you might just wind up a lonely old man someday.

Make use of Today’s Technology – Internet Dating
In addition to getting out and being seen, another very valid way to “gather new leads” in today’s midlife bachelor world is to take advantage of the various on-line dating services that exist.  What makes such services great is that they are full of women who want to date … they are in a sense, a catalog!  All types of on-line dating services exist – some are targeted at specific groups of people (like professionals, or millionaires), others are targeted at specific ethnic groups, others target literally everyone.   You can also find some seedy services that focus just on sex … with specific types of fetishes like swinging, etc.   As a midlife bachelor, I’m not going to recommend any one particular site – but I am going to presume that you are ultimately interested in a relationship … so I am going to recommend that you stay away from the sex-targeted websites.   My theory is that if you go in that direction once, it might become tempting to stick with that easy solution to one’s physical needs … and that could definitely interfere with your ability to meet a nice, decent woman in the future.  In other words, I view those sex-only websites as akin to visiting a prostitute – it’s a bad precedent to set, so don’t go there even once.   To answer your next question – no, I’ve personally never paid for sex, and I’ve never joined or met anyone on one of those sex-based websites.  Maybe that makes me stuffy or experience-limited – that’s for you to decide.

Okay – so you have my suggestion on what to stay away from … now what?  Well – you might consider trying one of the many more normal on-line dating websites.   As I said, I don’t want to recommend any – but we all see the ads for them. appears to be more of a zip code based catalog approach – you join, complete a personal profile, load in a photo or two … and then you can browse all the women within some number of miles of where you live. advertises heavily – they promote their multidimensional personality analysis … and claim to focus on matching you up with women who appear to be most suited to you.   There are tons of other on-line dating services – so recognize that I’m not recommending any one particular site … I’m just using two of the most common ones as examples, and briefly explaining how they appear to work.  If you decide to try on-line dating, it will be up to you to figure out which one is best for you.  Keep in mind that you don’t have to stick with just one – you can join two or more at the same time.   And if one such service is not generating any new activity for you within, say three to six months – I would suggest dumping that service.

When you sign-up for any on-line dating service – there are two things you need to be keenly aware of:

  1. What you put in your profile
  2. How and what you communicate to the women on the site

As far as what to put in your personal profile – this is a difficult thing to coach someone on.   My general recommendation is that you be truthful, yet political about anything you write.   You need to sound positive, happy, and like someone who would be interesting to meet.   You don’t want to put anything negative or cheesy in your profile – as that will tell the world that you are loser.   You also want to be very careful about what photo or photos you choose to display.   Don’t use a photo of you and your buddies dressed in wifebeater t-shirts and baseball caps turned backward, holding beers, and toasting the end of a football game at your house while yelling,  “YEAHHHHHH”.  Photos like that tell women that you are a party animal – and that is not typically the type of message you want to convey if you are serious about finding a new girlfriend.   A better bet might be to include several photos – the first being a good, clear photo of you … maybe even a professionally-taken photo.   This shows women what you REALLY look like.  In other words, if you are wearing a baseball hat in a photo – you might be bald … and some women really do not like bald men.   So why leave any doubt?  Why risk meeting a woman only to find out she thinks you are funny-looking?  Better to be up-front about everything – don’t lie, and don’t hide anything.  Subsequent photos are also a great idea – maybe show off what you look like overall … a full body shot of you somewhere, doing something.   This will tell the woman that you are not (or are?) fat or skinny … how you dress yourself when you are out in the world, etc.   Be careful about showing photos of you at party places like bars or anything similar … as you want to be very conscious of the self-image and the subtleties you portray.  Vacation photos are great – like if you recently went to Europe or Hawaii or Mexico or somewhere interesting.  Obviously do not use any photos of you with your wife or last girlfriend – as that is cheesy.  You also don’t want to use any photos that make otherwise cheesy statements – like a photo of you in front of your new midlife crisis Corvette … or a photo of you in the gym benchpressing some huge weight.   Just be mindful of the statements your photos are going to make.  Put yourself in the position of the woman looking at those photos, and ask yourself if such photos would really attract the type of woman you want to go out with.   It’s all about the messaging … the message you are trying to convey through your photos.

Just as important as the photos, what you write in your on-line dating profile is extremely important.   How you write it is also very important.   First of all – be mindful of your grammar and spelling.  If your profile has tons of spelling errors and/or grammatical mistakes – that’s the first thing that most women will notice.  Bad spelling and grammar tell the world that you are either uneducated, or that you don’t care about how your profile appears to others   Neither of those traits are good – so I would recommend that you compose anything you write using a word processor that has a spell-checker and grammar-checker, then cut-and-paste the spell-checked and grammar-checked text into your profile.   Good spelling and grammar are no substitute for good content, but they are certainly a key part of your overall presentation.

The content of what you write in your on-line profile is also make-or-break in terms of your potential appeal.  You want to appear to be a positive person who is interesting … you want to highlight things about yourself and your activities that draw in the type of woman you seek.  For example, you probably don’t want to say that your interests include smoking marijuana and drinking beer with your friends.  You probably also don’t want to discuss why you are recently a midlife bachelor, “My bitch wife cheated on me, and so here I am” … NO!!!   Instead you might consider saying something about enjoying fine dining, or eating at new places … or going to new places … or traveling abroad.   You could briefly discuss outdoor activities you enjoy like hiking, or play softball.   The whole idea is that you want to sound active and fun … willing to try new things … while at the same time appearing to live a balanced life.   I’m not telling you to lie on your profile – rather I’m suggesting that you give some thought to how you present yourself.  And if you don’t have any outside interests or activities or anything that even remotely makes you interesting … then maybe you need to get a life before you start to go out and date!   Just remember – when you are writing your on-line profile, put yourself in the reader’s chair, and try to understand how a prospective woman might interpret everything you write or expose about yourself.  If you put your profile out there, and don’t get any worthwhile responses within a month or two – then you probably need to consider revisiting either the photos, or how you’ve worded the profile or something … because there is always someone for everyone, and you should at least get some potential matches.

What successes have I had with on-line dating?  A few – I met a really nice woman named Joyce several years back on one of those sites.   Joyce scared me because she responded to my profile – but she had no photos posted.   I thought at the time that if someone doesn’t post a photo, she must be funny-looking – but that was not true.   Joyce actually just did not want to be recognized publicly, and that was fine.   She understood that I was skeptical about meeting her – so I had her introduce herself in person to me in a local grocery store – in the buns and rolls section (which sounded just a little better than the meat section).   I thought she was pretty cute – and after the intro-meeting, we went on a real date that weekend … and she wound up being one of those very horny divorcees who could not get enough sex.

The other success I had with on-line dating was with Debi the nurse.   Once again, Debi did not post a photo – and once again, I was very skeptical.   Debi turned out to be really good-looking though – and I was not disappointed at all.  I believe I mentioned before that after Debi and I went out several times – we wound up getting quickly and seriously involved in a powerful sexual affair with one another … and wow was that nice.

Neither of the women I met on-line wound up being permanent girlfriends – although both lasted a respectable amount of time … similar to women I would have met without an on-line matchmaking service.   So I would call both Joyce and Debi success stories for on-line dating … thus I am a believer.   Friends of mine have not been so lucky.   My buddy, Mike, tried on-line dating, and basically failed – but I think that was because his follow-up and conversational skills were developmental (actually those skills of his are horrible – but I was attempting to be kind).   Several of my female friends have also tried on-line dating – and the reports I have been given are fairly spotty.   My interpretation of their experiences is that they hooked up with several guys briefly … had sex with them … but the relationships ended fairly quickly (like within several months).    Truthfully, I would say that – in my opinion – meeting someone on-line is pretty much the same as meeting them around town … you meet them, you date them, you learn more about them, and then (often) you move on.   The nice difference about on-line dating is that you do get the chance to somewhat pre-screen them … see what their interests are, their basic statistics, etc.   [You cannot walk up to a woman in a grocery store, and ask to see her profile before you talk to her, right?]

Okay – so this officially concludes Step 2, “Conquer the Basics and Start Dating”.  We’ve discussed how to generate new potential women to go out with, we’ve discussed how to ask them out, …  how to prepare for the first date …  what to watch for during the date … the goodnight kiss PLUS we’ve also discussed the concept of deciding whether to continue dating a particular woman.   The whole point of Step 2 is to get you out and dating, and used to all of the things that can happen to you while you are trying to date.  Practice makes perfect – and many midlife bachelors are extremely OUT OF PRACTICE … so hopefully I’ve given you many things to think about.   Remember that Step 2 is really Step 2 of your Strategy for Midlife Bachelor Success … and the next element of your overall strategy (once you’ve gotten over the HUMP of learning to date again) is to date successfully the woman you think you really want to date.

>> Developmental Dating

Asking for the Date
Okay – so in our overall “developmental dating” journey, right now you have been coached on how to identify a woman who likes you, and who (hopefully) you like and want to ask out.  Now comes the part that some people who have not been single in quite some time dread – the actual act of asking a woman out on a date!   How do you do it?  How DON’T you do it?  Are some ways better than others?  The answer is actually very much an individual answer – what works best for some is not necessarily the best for others.   Often times the ease of asking a woman out is directly related to how good-looking you are – which never helped me any because I’m very average-looking.

Anytime I planned ahead to ask a woman out, I would almost always be nervous about it.  My degree of nervousness was usually a function of how comfortable I was around the woman … how certain I felt my chance of success was.  For me, I always did better with women I had known for a while and had a chance to build some sort of rapport with over time.  That way I could usually tell if they were interested in me, if they had a current boyfriend, possibly what kind of woman they are, and also what kind of things they liked to do … maybe what kind of food they liked, or what interests they had.  It always seemed easier for me to ask a woman out when I knew a lot about her.  I would generally ask a woman out on first date to lunch or dinner – in a very easy-going way.  In other words, I wouldn’t start out a conversation with a date-shot … rather I would work it into the end of my conversation with her.

       “You want to get something to eat after work later this week?”

or maybe

       “You want to have lunch with me at <restaurant name> one
day next week?”

The question has to flow within your conversation – so don’t just pop it out, otherwise it might sound weird.  Sometimes you might even have to practice it beforehand – but don’t make it sound rehearsed.   My advice is that you do not appear overly anxious and that after you ask – don’t ask a second time.   If she is interested in you, you’ll get an answer right away.  If she doesn’t answer directly, take that as a “no thank you” and move on gracefully.   Whatever you do, do not pester the woman!  That will lump you into the stalker category and turn her off (or possibly scare her).

Assuming she agrees to go out with you, the next thing I would typically ask for is her phone number – or some means of contacting her to confirm the date.   Again, I would personally do this in a very non-intrusive way, such as

       “Can I get your cell number, or should I just call you here
the day before?”

Assuming you are at work or her work – it is often less invasive to offer to call her there if she says it is okay.  Some people (myself included) are hesitant to give out our cell numbers until we know someone.   Notice that I did not offer my cell number in my example dialog … because you just don’t know if a woman is psychotic until you date her at least a few times.  In other words, I use my cell phone for work a lot of the time – and the last thing I ever would want is a woman hammering my cell phone with calls during the day … which some women will do.   I try to avoid any possible menaces – so I don’t like to give my cell number out.  Expect that some women will feel the same way, and don’t be insulted if she won’t give you her number at first.

The First Date with Any Woman
Maybe some of you midlife bachelors reading this section think this is all an unnecessary discussion.  Perhaps that is true for you – or perhaps you might consider it an excellent personal refresher course.  Maybe your skills as a gentleman could use some polish?  Maybe not.   If you genuinely feel this is boring you – then please skip ahead.  I think it is all very valuable – it never hurts to hear input from someone else, right?

Okay – you’ve got the woman to agree to the first date, and all either of you knows is that it involves a meal, for example.   First, be sure to confirm the date ahead of time.  If you asked her out more than several days in advance, call her the day before and verify that you are still ON.  If you have to leave a message, that’s fine – just be brief:

     “Hi, this is Greg, and I just want to make sure we are still on for dinner
tomorrow night.   I’ll pick you up (or meet you, if that is how you left it)
at X:YZ p.m., and we’ll go from there, okay?   Call me back and let me

Of course, you are now stuck with having to leave your phone number – so cross your fingers in this case.

Several things to remember before picking her up for that first date:

1)   Dress appropriately for where you are taking her

2)   Keep all of the basics that you learned in The Midlife Bachelor Personal Makeover in mind

3)   Be on time – this is important.  If you are running more than ten minutes late, call her and tell her what is holding you up. Women HATE to be left waiting.

4)   Have reservations made for where you are going, if appropriate.

5)   Make sure your car is clean or reasonably clean.  No one wants to date a slob!

When you pick her up for the date, or when you meet her somewhere:

1)   Tell her that she looks nice (assuming she does look nice).

2)   Be a gentleman.   This means different things to different people. For me, I am the type to open doors for a woman.

3)   Don’t go overboard on the gentleman stuff.  Don’t try to order her meal for her, for example.   Try to be considerate, and stick with all the basics.

4)  Keep in mind the conversational suggestions from the Midlife Bachelor Personal Makeover section.   Don’t talk too much about yourself, and try to get her to talk about herself.  Try to figure out common interests based on what she tells you … in other words, LISTEN to what she says.

5)   Don’t look at other women or be flirty with the waitress.   This is just common sense, but some midlife bachelors don’t know
any better.

6)   Plan the date loosely, and allow for spontaneity.

If your first date is going well, time will seem to pass quickly for both of you.   Keep in mind that even though you might be having an excellent time, she might not be for various reasons.  It might be something you said or did or didn’t say or didn’t do.  Hell – you might never even know why she didn’t have a good time … it might not even have anything to do with you.  [For example, she might feel wrong about going out with you because she recently broke up with a boyfriend that she cares about.]

Watch for Signs or Signals  on the First Date or Two
You’ve got to watch for various signs that she may be giving you, which can signal how the first date is going from her perspective.   For example, if she looks at her watch or cell phone frequently, she thinks it is time for the date to end.  If she seems bored after a while and stops engaging you in conversation – that is also a signal that the date should end.   If she comes over and sits in your lap and starts kissing you – that is a sign that the evening is going great and probably just getting started.   Everything is situational – there are countless signs that she could give you.   Don’t be overly analytical, and don’t necessarily call out what you think you see her signaling … but do keep your eyes and ears open, and try to act appropriately.   For example, if you notice her constantly looking at her watch or cell phone – you could ask her something like, “Is it time to go?”  She might respond with something you are not expecting – like she is concerned about her children with a new babysitter … and that is why I say it is best to not be overly analytical.

Positive signs or signals a woman gives you can be sometimes be either subtle (hard to detect), or sometimes they can be really overt or obvious – it all depends on the woman, and also on how comfortable she is with you.   Usually women will become more comfortable with you the more they see you – so don’t necessarily expect her to fall for you immediately.  I’ve found that if you listen very carefully to what a woman is telling you, you can pretty much gauge where she thinks things are going between you.  If she hints at going somewhere you can be alone, then you can guess what she might be thinking.  If she talks subtly or not-so-subtly about sex – you can bet that sex is on her mind, and that you might just be getting lucky sometime soon.

  The look  – I’ve found that women who want to either make-out or have sex will almost always give me what I call “the look”.   She just looks right at you in a very distinctive way.  Not like you have a zit on your nose – but more like an extremely attentive eye-locking stare.  To me this look is unmistakable.  You will know when you receive this look.  If you are on a first date with a particular woman, you might not get this look until you are telling her goodnight – or you might not get the look at all.  If you don’t get “the look”, don’t take it personally – sometimes women take a while to warm-up to you.  Or sometimes the chemistry just isn’t right for both of you.  There is no right or wrong – it is just what it is.

Saying Goodnight or Goodbye on the First Date or Two
Your first or second midlife bachelor date is coming to a close.  You are pulling up in front of where she lives.  You have not kissed her before, nor had any contact of this sort yet with her.   What do you do?   Refer to the golden rule of midlife bachelorhood (which I introduced in the earlier section entitled “Some Fundamental Truths about Women and Midlife Dating Today”) – ALWAYS GO FOR IT.  Okay – so let’s keep this golden rule in context.  You have to ask yourself several questions before attempting your next move:

  1. Did the date go really well from your perspective?
  2. Did she seem to have a good time?
  3. Was there any detectable romance whatsoever between the two of you during the date?  [In other words, did she give you any signs whatsoever that she is really interested in you?]
  4. Do you think she is hot?
  5. Does she seem at least somewhat approachable for a kiss?
  6. Does she respond favorably about possibly wanting to go out again?

If the answer to all of these questions is YES, then you owe it to yourself and to her to attempt to give her a goodnight kiss .   What kind of kiss – a peck or a mouth full of tongue?  That is very situational and hard to answer – you have to figure it out for yourself at the moment your lips touch.  If she is a very conservative woman, then probably a peck is best at first – unless she opens her mouth when you kiss her (in which case YOU GO FOR IT).  If she does not appear conservative, then my advice is to go for a full-on French kiss, and see where that takes you.   Sometimes women put on this “good girl front” the first several times you go out so that you don’t think she is a slut.  If she shuts your effort down, don’t be insulted – just smile, and tell her goodnight … and that you would love to see her again soon.

I’ve had first dates run all over the map in terms of how they’ve ended.  It really depends on the woman, how “in to” you she is, and also where she is in terms of needing attention or physical contact.  Religion doesn’t matter – religious women will respond just like any other woman … although they might tend more toward being conservative AT FIRST.  Remember Linda – the religious brand-new divorcee?  She was very religious, and taught Sunday school … but when she came over to my home for a visit, her son was tired so we put him in the next room … and then within a few minutes we were making out, and I was rubbing her crotch with my hand … first outside her underwear, then inside.   She was going crazy – but we didn’t have sex that time (because her son was in the next room).   Then there was the Mormon woman named Kristy – who always talked about church and being LDS.  But as soon as I had her out to dinner, she started drinking and then wanted to go back to my home … where she had sex with me the first night.

Other women in my past were not such fast movers.   There was Andrea who worked at the local BMW dealership as the cashier.  I dated her for weeks before she actually had sex with me – although she did make-out with me on our second date.  She had kind of a strong personality – and was fairly controlling in terms of everything.  She was a tough nut to crack – but I remember that after several weeks of dating her, I was making out with her and I just flat out asked if we could now have sex upstairs in my bedroom.  She was a little put off by my directness – but said “okay”, and that’s when I found out how much fun she really was.  I had sex with her twice in that first session – and I remember that her body kept shaking and shaking after each orgasm of mine … because she had not had sex in quite some time, it turned out.  Andrea was a little chunky – but there was something extremely sexy about her.   Even when I was mad at her, I still wanted to give it to her … which is kind of rare for me, quite honestly.  Anyway, that “controlling” aspect of her personality is what eventually did us in as a couple – we clashed because I am also controlling.  But it was a fun couple of months.

The Three Date Rule
Should midlife bachelors have RULES concerning how long is too long to wait to sleep with a woman, or to kiss her?  Absolutely it is fine to have such rules – but best to keep them as good reference points, and not necessarily firm rules.  Some midlife bachelors will tell you that if a woman doesn’t have sex with you within three dates, then she either has some other action going on or is frigid   There may be some truth to that – but I think that in many cases, some women just move more slowly than men.  Plus I think it can be very situational – like if the woman is freshly divorced, she is much more likely to want to have sex than if she has been divorced several years, and is over the phase where she needs constant sexual gratification.

For me, I always used “the three date rule” as a reference point to decide whether to continue seeing a particular woman.  Some women are really conservative – and it would take me three dates to just get a decent kiss out of them.  Other women were the opposite of conservative, and by the third date we had already had sex one or more times.   I would suggest that you use “the three date rule” as a milestone for deciding where you think the relationship can head … if you want to pursue it INDEPENDENT of whether you are already having sex with a woman.

One thing I can say with certainty for me – and that is that if a woman has not allowed me to really kiss (French kiss) her by the third date, then I can pretty much assume that the relationship is destined for friendship … or something other than a hot physical relationship.   Friendships with women are fine – in fact, they can be critical for a midlife bachelor to network through to other women.  So just because a woman winds up being more of a friend, don’t write her off … use her as a reference point.  If she thinks highly of you, then she is much more likely to want to hook you up with one of her friends.

Time to Dump her?  Another possible scenario is that after three dates, you find the woman completely annoying.  You don’t want her as your friend, and even if you have had sex with her – you really cannot stand the sound of her voice, and you need her to be out of sight and out of mind.   This is also completely normal and acceptable in the world of dating (it may even happen with you being on the annoying side).  Here you do not want the friendship – so my advice is that you:

  1. Tell her how you feel in the most polite way possible, or
  2. Stop accepting or returning her phone calls or emails, or
  3. First 1) then 2)

If you want to be polite and up-front, then tell her that you really don’t think the two of you have a future together, and that you are sorry … or something similar to that.  I believe it always pays to be very polite in situations like this because you would want someone to be polite to you if the roles were reversed, right?   Treat others as you would like to be treated – but don’t necessarily expect them to treat you how you expect.  So many people take being dumped way too personally – it really shouldn’t be that way.   If it happens to you, then move on and look forward to your next date.

What’s Next After Three Dates?
You know you can date any woman as long as you want, or as long as the two of you want.  If you were paying attention to the other sections of this site, then you know to watch out for things like wanting to marry the first woman you date (rebound), or for allowing great sex to mask the truth about the nature of a particular woman’s personality, etc.  My point – as a midlife bachelor, you need to periodically ask yourself if you are dating a particular woman for the right reasons  Is she really what you want in the long-term?  Have you reasonably sampled the various types of women out there to really know what you want in the long-term?  What happens when the hot sex wears off with the woman you are with – will you still want her around?   Are you settling for a particular woman because you are afraid of being single, or are afraid you won’t be able to do any better?

For me, the answers to the questions I pose above have always been reasonably easy for me to answer.  I usually know in my heart if a woman is going to increasingly annoy me … it is like a gut feel or something.  I will say that in many cases, I have kept a particular girlfriend around a lot longer than I should have simply because I enjoyed the sex … and I’m not entirely sure that was the right thing to do, but it seemed right at the time.  I didn’t keep them around until I found something better – usually I kept them around until I just couldn’t stand the relationship any more … or I felt that I was leading the woman on, and that it was no longer fair of me to continue to do so.   You will know what is right for you to do – just make sure that you are thinking about all the right things, and looking at the bigger picture for yourself.  You’ll make the right decision as long as you keep everything in its proper perspective.

Step 3:  Figure Out What Kind of Woman You are Looking for
                and Date Her

Let’s now assume or presume that you have mastered the art of dating … that you can ask a woman out, have fun on your dates, and turn a woman into your full-time girlfriend if you wish.   Since you supposedly know the mechanics of what you are doing, now might be the time to for you to start looking for someone you want to date (versus someone you simply can date).  The transition from being “able to date” to “dating who you want” is actually quite huge – and I don’t mean to minimize that hurdle by any means.  Some guys never make the transition … or never get to the point of being able to date successfully to begin with.   If you recognize these individual steps you are going through, and self-analyze where you are failing – you are much more likely to develop your own self-corrective action plan … which is Step 4 (which I’ll discuss shortly).

To successfully transition from Step 2 to Step 3, you need to have some sort of idea what kind of woman will make you happy in the long-term.   This is a hard question to answer for many of us.  Many midlife bachelors initially focus on the wrong attributes – like basing requirements purely on looks, and/or great sex.  It seems like the longer I have been a bachelor, the more I have focused on a balance of characteristics … nice-looking, nice teeth, good family, high integrity, and easy-going seem to be the attributes of women that I have enjoyed dating the most.   Of course, my own history is spotted with exceptions to women with those qualities.   For example, whenever I have changed girlfriends in the past, I usually go from the “quiet conservative” type over to the “hot-looking party chick” type, and then back again.   For example, Joyce was the hot divorcee I met on-line – she was very quiet and conservative (except in the bedroom) … but honestly, I got kind of bored with her over time … and so the next woman I dated was Debi the hot Latina nurse … who drank excessively, but was a ton of fun in the bedroom as well as overall.   They say the hottest fires burn out the quickest – and although Debi lasted more than a year, that relationship was probably doomed from the start (because she was such a party chick).   I knew in my heart when I was dating Debi that the woman I needed long-term was someone more conservative … someone who didn’t drink huge amounts of alcohol every night … someone who didn’t yell at me in public places …  someone more like Joyce, but who I wouldn’t get bored with.   Mine is a tall order – and maybe that is one reason why I’m still not married!

You’ve got to figure out what type of woman is right for you.  You have to date a bunch of different types of women to know what suits your personality the best over the long haul.  As I mentioned earlier, you cannot jump to a particular conclusion in your first year of midlife bachelorhood (rebound scenario) because you just have not experienced enough of the women out there to know for sure what is best for you.  My advice is that you give everything time … the time for you to date different women, and be better self-educated on what YOU NEED in a relationship.   I caution you to look past good looks and good sex – those things fade out over time … they are the last things you want a long-term relationship based on.

How do you know what “the right kind of woman” for you is?   Okay – so if you follow my advice and minimize the impact of sex and good looks on your choice for your long-term relationship, what do you look for?   The answers are unique to you and your personality and needs.   Here are some core qualities to consider and where or how, or why they might be appropriate.   They are not in any particular order.

  1. High integrity is a tremendous attribute that can be hard to find … a loyal and trustworthy woman.   Assuming that you, too, have high integrity, then this is a great attribute to seek.
  2. Cash cow – I use this term somewhat jokingly – I am referring to a woman who stands on her own two feet financially.   The best “cash cow” woman can support you – imagine you, me, and your buddies drinking beer on a Tuesday afternoon while lounging around her pool while your cash cow wife or girlfriend pays all the bills.   That’s what I’m talking about.   A cash cow is also referred to as a “jackpot” type.
  3. Trusting – a woman who trusts you (and does not get jealous) is rare.  Finding a woman of this sort is akin to discovering gold or oil in your backyard … don’t sell the house, just enjoy your wealth of freedom without harassment!
  4. Independent – an independent woman does not need you to give her focus and direction.  Some women are independent, some are co-dependent, and some are just plain dependent.  Independent is best (in my opinion), but you need to decide for yourself what level of independence (or co-dependence or dependence) is best for you.
  5. Fun factor refers to how fun a particular woman is in the long term.  What is fun?  Fun is the ability to have a good time with her wherever you go together.   Fun is not fighting.  Fun is romance.   Fun is and is not many things – but the key to fun is that you enjoy being with her … she enhances your life and brings a smile to your face.   Don’t assume that all relationships are fun – they might start that way, but many relationships degenerate into no fun over time.   I don’t know of an excellent way to predict long-term fun – indeed, my historical gut feels have not been accurate predictors of long-term fun factors.
  6. Nice teeth – okay, this is highly superficial of me to call out here, but it is something that I give weight to.  I like nice teeth a lot – and I think it is a decent predictor of long-term hygiene.  Plus, a woman with nice teeth is less likely to generate large bills at the dentist!  “nice teeth” mean they are white, straight, and well maintained.
  7. Good looks – I said to be careful about over-weighing this particular characteristic, but you have to attach some value to it.  I’ve found that the better-looking a woman is – the higher maintenance she is overall … so there is some personal magic balance you have to figure out for yourself concerning a beautiful woman you are considering keeping as a long-term girlfriend.  The critical question to ask yourself is – is whatever maintenance she requires going to annoy me where I don’t want to be around her?   Sometimes this question is easy to answer. Other times. It isn’t easy.  Look past the great sex – does anything else she does get on your nerves, maybe a little?  If it gets on your nerves a little right now, it will get on your nerves a lot more in the future.   Like the hot Latina nurse Debi’s a hard-drinking, it ultimately really caused many problems between us.
  8. Sensual sex – good sex is different from good looks because you can have great sex with a not necessarily great-looking woman.  I’ve had plenty of good-looking girlfriends, but I think some of the best sex was with women who were not the hottest.  Okay – I’ll be honest, I’ve had sex with some chunky monkeys in my day.   Not huge, but certainly not skinny.   Most of them were very short-term for me … as they were too large for me to consider having a long and public relationship.   These less-than-ideal-looking women were great sex partners because they craved the sex … they were really into it, and we’re regretful.   I won’t go into this, as I think you get the idea.   My point is – to give careful consideration to the degree of sexual fun you have with a particular woman.  Dooveremphasizesize it because the frequency and fun factor of that sex will diminish over time.   Recognize that you cannot base a relationship solely on sex – such relationships are doomed as soon as the thrill of the ride is gone.
  9. Religious – this might be a key discriminator if you are a born-again Christian or similar.  If you are not religious (like me), you should probably avoid someone extremely religious – as it is likely to result in long-term conflict.
  10. Good family background – this is not as subjective as you might think.  She either comes from a good family, or she doesn’t.   A good family might be somewhat dysfunctional, but not overly so.  A woman who comes from a good family understands family values and the importance of taking care of herself.  I’ve found that the women from the worst families or the most screwed-up families make the worst girlfriends. If they are accustomed to many problems within their own family, they will think that a lot of problems or issues or trouble with you are business as usual.   And midlife bachelors don’t want any problems, right?
  11. Kind-hearted – a woman who is kind to everyone is more likely to be kind toward you when the chips are down, or things are rough in your relationship with her.  A kind woman is much easier to deal with than a mean-spirited one.   A kind woman looks for the good in everyone first and foremost – and lives her life in a way that everyone can be proud of.  You won’t have to bail a kind woman out of jail.  You are less likely to argue with a kind woman.  A kind woman won’t beat you up, or throw things at you.  I view being kind as one of the most important characteristics of a woman that I stick with – everything is just so much easier.

The qualities I discuss above are just some of many possible which may or may not be important to you as a midlife bachelor looking for love.  Some of them are important to me – others are not.  Most of the time you cannot have EVERYTHING you want in a woman – there is always some kind of overall balance or compromise involved.   The lack of some qualities might be a show-stopper for some of us.  My friends who are born-again Christians would never date someone who is not also a born-again Christian, for example.  For me – bad teeth are a definite show-stopper … she could be beautiful, rich, kind, come from a good family, have high integrity, etc. – but if her teeth are extremely jacked up, then I don’t think I could go near her!  Superficial of me – perhaps … but I’m being truthful here!  My point is that some qualities are mandatory, some are optional, and some are a bonus.

Focus on Meeting the Right Type of Woman.  After at least a year or two of being single and dating different types of women, you should have at least some idea of what is out there and also what key qualities of a woman are important to you.   You might also have learned something new about yourself – like you have a particular attraction to certain types of women (like blondes or Latinas or large boobs, etc.).   Hopefully, you have also dated women who have characteristics you know are incompatible with you in the long-run … such as excessive drinking, throwing punches, yelling at you in public, or being jealous, etc.   Based on what you have learned about yourself, make a list of what you are looking for in a woman and what you are NOT looking for.   [This doesn’t necessarily have to be a written list – but that helps.]    Assuming you want a long-term relationship (which most of us do), you need to seek a woman with the features you desire actively.

How do you meet her?   That is the $64,000 question!  The answer is highly dependent on what you are looking for in a woman.   If you are religious, the solution might be a little easier – you look for her at church and church-related functions.   If you don’t meet her at your church, then change churches.  I do not mean to mock religion by suggesting you choose a church based on where the single women are … my point is instead that you expose yourself to different congregations with the hope of meeting someone suitable.   I’m not a religious person, so I’m not speaking from experience, but I have a fun story.  I’m Catholic, and one of my friends named Robert is a severe Catholic … he does the Bible reading at the Sunday Masses, participates in many local church-related events, etc.   Years ago, he invited me to start going with him to the church’s weekly Catholic adult education classes on a weekday evening.   I asked him somewhat jokingly if there were any single women there – and he said, “Yeah – sure … some, I suppose.”   The point of going was for the Catholic lecture, not the women – but I remember thinking to myself, “hmmmmm.”   So I attended one of these sessions – and there were about twenty-five adults of various ages there – including a handful of women.   After the lecture, two women came to me and introduced themselves … noting that they had not seen me there before.  This was very friendly of them – and I appreciated it … but these women were HUGE.  I guess I looked like fresh meat to them at the time – not sure if they wanted to date me or throw me on the barbeque.   Anyway, my friend, Robert, got a great laugh out of the whole situation – he knew these women were shark-like and that they would try to contact me!

How do you meet the right woman if you are not religious?  The answer rests with what you find essential in a woman.  It might also be a function of what ethnicity you prefer.  You need to try your best to place yourself wherever your “target” female is likely to be found.  This can be very difficult to do with precision, but it can be done more generally so that you at least increase your odds of meeting someone with the desired characteristics.   If you like career women, go to restaurants where well-dressed women congregate for happy hour – not the local biker bar.   If you think physical fitness is critical – try to focus on meeting women at your gym.   [Maybe even join a second gym to mix things up a little.]  In general, try to place yourself in locations where the type of woman you want is likely to hang out.  It may work – it may not.   You can also try online dating and tailoring your profile to attract specific types of women – but try not to sound too exclusive, as that can be a turn-off.   Just try as many new locations or options as you can – and remember not to let rejection slow you down.  You have to be deliberate and proactive in your search – the woman of your dreams typically will not come to you. Instead, it would help if you found her.

The key to finding the right woman is to keep dating different women until you meet her.   Keep in mind that some women are “sleepers” – good catches but difficult to recognize them as such at first glance or on the first date.   So keep an open mind, and if you enjoy hanging out with a particular woman, keep dating her until you know whether she is someone you’d like to stay around for an extended time.  If you decide she is probably not a good long-term match for you, I encourage you to break things off in as friendly a manner as possible … so that you can continue to network through her.  Your “Miss Right” (or “Ms. Right”) might be one of her friends … but you will never meet that friend of hers if she thinks you are an asshole!

Step 4:  Periodic Re-evaluation of your Midlife Bachelor Strategy

The final element of any good midlife bachelor strategy for success must always be a periodic re-evaluation of your current system.   Every couple of months, you need to take inventory of everything and figure out what you have learned about yourself, the effectiveness of the way you are conducting yourself, how you are attempting to meet the woman of your dreams, etc. … and then you need to make the necessary adjustments.   Every midlife bachelor out there is going to make mistakes … is going to have a unique set of personal challenges to overcome.   It is OK to make mistakes – everyone does.  The key to moving forward with your life is to learn from those mistakes and not repeat them.   You most definitely need to take the time necessary to look at your actions and attributes and differentiate between standard rejections you may have received versus rejections you’ve received due to misplaced effort on your part.   In other words, if you are repeatedly failing at some aspect of dating – you have to ask yourself why and then adjust what you are doing accordingly.

For example, let’s say you cannot for the life of you get a damn date.  There could be many reasons for this – but there is always a solution.   It might be that your teeth are jacked up – so get your ass to a dentist or orthodontist immediately.   It could be some other element of your appearance – like maybe your sense of overall fashion is poor … so get some advice from a good female friend, and buy the kind of clothes that she suggests. Perhaps the problem is behavioral, not physical – perhaps you are asking out women who are “out of your league” … too good-looking to go out with someone like you.  The solution is to lower your standards until you find your equilibrium point.   I’m not necessarily saying you should date the chubby/homely women – but kick everything down a notch and get some experience dating.   You might get more comfortable and successful with better-looking women after your self-confidence improves after dating a few lower-tier women.

My “day job” is being a sales manager for a technology company.  Some of the products we make are real-time control systems.  These systems run an algorithm that keeps whatever they control within a certain tolerance.   They contain some critical process – which could be anything.   It is analogous to your home thermostat – you set it at a specific temperature, and either the heater or the air conditioner kicks on whenever the temperature goes past a certain threshold.  Step 4 is all about YOU being the control system or the thermostat …  if you drift too far out of the desired range, then you adjust yourself to get back where you need to be.  But instead of just a hot/cold air adjustment, you have many more potential personal variables to work with.   Go through all of the individual items that I’ve discussed in this and previous sections – the more detail you dive into about yourself, the more likely you are to be able to optimize yourself and your strategy.  If you are aware of every single aspect of yourself, you will eventually figure out what you are doing right and what you are doing wrong.  If you are unsure, ask a female friend or two for their opinions.   Trial and error are satisfactory – that often is the only way for a midlife bachelor who is extremely out of practice to determine his strengths and weaknesses as a single man.  Don’t ever give up – just re-evaluate, and be ready to make the necessary adjustments.   Leverage your strengths, minimize your weaknesses, adjust your strategy accordingly – and move forward with your life, my brother.

Avatar of Greg Smith
About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.