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Develop a Strategy for Midlife Bachelor Success

Step 3:  Figure Out What Kind of Woman You are Looking for
                and Date Her
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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, then what do you look for?   The answers are unique to you, and your individual 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 – this is a tremendous attribute that can be hard to find … a woman who is loyal and trustworthy.   Assuming that you, too, have high integrity, then this is a great attribute to seek.
  2. Cash cow – I use this term somewhat jokingly - what I am referring to is a woman who stands on her own two feet financially.   The best “cash cow” women can actually support you – imagine you, me, and your buddies drinking beer on, say, 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 what I earlier referred to as a “jackpot” type.
  3. Trusting – a woman who trusts you (and does not get jealous) is a rare find.  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 – a woman who is independent 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 in the long-run.
  5. Fun factor - this 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 out that way, but over time many relationships degenerate into no fun.   I don’t know of a good way to predict long-term fun – certainly my historical gut feels have not been accurate predictors of long-term fun factor.
  6. Nice teeth – okay, this is extremely superficial of me to call out here, but it is something that I personally 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!  To me, “nice teeth” means they are white, straight, and well maintained.
  7. Good looks – I said to be careful about over-weighing this particular characteristic, but you do have to attach some sort of value to it.  I’ve personally found that the better-looking a woman is – the higher maintenance she is overall … so there is some sort of personal magic balance you have to figure out for yourself with respect to a good-looking woman you are considering keeping as a long-term girlfriend.  The key question to ask yourself is – is whatever maintenance she requires going to annoy me to the point where I don’t want to be around her?   Sometimes this question is easy to answer, other times it is difficult.  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, chances are that it will get on your nerves a lot more in the future.   Just like the hard-drinking of the hot Latina nurse Debi – it ultimately really caused a lot of problems between us.
  8. Good sex – good sex is different than good looks because you can have great sex with a woman who is not necessarily great looking.  I’ve had plenty of good looking girlfriends, but I think some of the best sex I had 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 with.   The reason these less-than-ideal looking women were great sex partners is that they craved the sex … they were really into it, and were grateful as hell.   I won’t go into this any further, as I think you get the idea.   My point is – give careful consideration to the degree of sexual fun you have with a particular woman.  Don’t over emphasize it, because the frequency and fun factor of that sex will diminish over time.   Recognize also 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, yourself, are a born-again Christian or similar.  If you are not religious (like me), you should probably avoid someone who is 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 one’s own.  I’ve found that the women who come from the worst families, or the most screwed up families make the worst girlfriends – if they are accustomed to a lot of problems within their own family, then 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.

Next >>> Focus on Meeting the Right Type of Woman



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Develop a Strategy for Midlife Bachelor Success

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

        How long have you been single?

        Do you want to stay single?

        Are you better off being single?

        Rebound – Does fear of being single drive your behavior?

        Understanding your current needs vs your longer-term needs

        Define your objectives

               Midlife Bachelor Objective Roadmap

   Step 2:  Conquer the Basics and Start Dating   

        Developmental Dating

               Identify a Potential Date

               Asking for the Date

               The First Date with Any Woman

               Watch for Signs or Signals

                     The Look

               Saying Goodnight or Goodbye on the First Date or Two

                     Goodnight kiss

               The Three Date Rule

                     Time to Dump her?

               What’s Next After Three Dates?

        Lead Generation – Finding New Women to Date

               Get Out and Be Seen

                    Always Say Something

                          Use What You’ve Got 

                                Exploit your personal strengths

                                Minimize Your Weaknesses

                    Maximize Your Opportunities

                          Plant seeds in the overall community of women

                          Leverage your friendships

                               Go on a Blind Date

                          Pick the low-hanging fruit first

               Make use of Today’s Technology – Internet Dating

   Step 3:  Figure out what kind of woman you are looking for and date her

        How do you know what the right kind of woman for you is?

        Focus on Meeting the Right Type of Woman 

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