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Develop a Strategy for Midlife Bachelor Success

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

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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 with respect to myself, or with respect to people I know.   Remember – you can learn just as much from watching others as you can from watching yourself.

How long have you been single?   In terms of goal setting and the establishment of an overall midlife bachelor strategy, much can depend on how long you have actually been single.  You have to carefully consider where you are with respect to your own “relationship readiness” … which is a product of your own history, and that history’s affect on your current mindset.   You’ve got to factor all of this into the goals you set, and the strategy you establish for yourself so that you can keep everything realistic.   Your past strongly influences your current state of mind, and often the more recent that something major has occurred, the stronger the influence it will have upon you.   Here are a few examples that relate to 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 very difficult 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 last long-term relationship was a continuous living hell, then you likely have some personal issues to deal with before you can really 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 is going to cheat on you.  

Here’s a different scenario to consider – again, let’s assume you are a brand-new midlife bachelor … but this time the reason you are now suddenly single is that 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 any example case, you always want to focus yourself on 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 any of this here … when we are 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 rather you are “perpetually” a midlife bachelor.  In a case like this, you obviously have some sort of 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 personally know several guys in this exact situation … some might even argue that I, myself, fit this profile, too.   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 “selfish”, “self absorbed”, “domineering”, “controlling”, “manipulative”, “unreliable”, maybe “cheap”, “racist”.  You get the idea – maybe 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 actually 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 while, and 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 in a very short amount of time … as that is essentially a rebound scenario, and is often doomed in the 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.

Next >>> Do You Want to Stay Single?

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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