Be Careful Right Out of the Starting Gate

This Fundamental Truth and the previous ones (be comfortable with yourself and don’t take things too personally) are all closely related.  When I say “Be careful right out of the starting gate”, I am referring to being careful and watchful during the first few months of a new relationship – because people (yourself included) are usually on their best behavior.  Sometimes subtleties snowball.  Sometimes things that might bug you just a little when you first start dating someone will eventually bug you a whole lot!  I am a big fan of initial “gut feelings” about people – as they have almost always proven to be correct in the long run.  Just be careful – keep your eyes and ears open, and make your own mental notes.  Over time, you will learn to trust your instincts about people – as I do.  If you know yourself really well, you will develop a midlife bachelor skill set that allows you to recognize rather quickly if a particular relationship can work (not WILL WORK but CAN WORK).  If you develop a pretty good feeling that a new relationship is not going to work out, then it is to your advantage to categorize it as a “false start”, and move on.  This will conserve everyone’s energy, and minimize any potential hurt feelings.

Great Sex Hides the Truth

Before I dig into several examples about being careful at the starting gate, it is important to state the obvious.  If you are having great sex with a woman, you will likely not care about anything else for a while … because sex is the ultimate mask!   The better the sex, the more likely you are to ignore any other potential incompatibilities.  I’ve known this for years, but I’ve never been able to get past it myself.  Even fairly recently, I’ve allowed sex to dictate the direction I took my life with respect to a relationship.

Okay – so the very cute blonde bombshell that worked at the local drug store up the street, her name was Becky.  I mentioned before that she was my friend, and that I had this long-standing crush on her – and that we met up around town one day, and started going to lunch together.  Before we started formally dating, we were already sleeping together – and wow was it ever fantastic.   I was so attracted to Becky that I could perform miracles – which meant that at age 38, I was able to have sex with her five separate times in one session.  And I had not done that since I was around 19 years old … I didn’t even think it was possible for me at age 38, quite frankly.  I just couldn’t believe how attracted I was to this woman.  Now granted that this relationship started off kind of backward in that we didn’t date before we jumped into bed – but I can say that as we started to date, I noticed right away that she had two qualities that really bothered me:

• She said things that made her appear trashy.
• She was very permissive with her 13-year old daughter in terms of dating.

In terms of the things she said that made her appear low class – she would say things like, “I have the pussy, so that makes me the boss.”  In fact, I remember her saying exactly that fairly often – and each time she said it, I thought to myself what a piece of white trash she was.  But then the next thing I knew, we would be in her bed or mine having a marathon sex session, and I would forget all about anything she had said.  I do remember wondering to myself how much she would annoy me when the red hot sex wore down.  Actually, I didn’t have a chance to wait for the sex to wear down – because she and I got into a huge fight over how she was raising her daughter.

I was very fond of Becky’s thirteen year old daughter.  In the three short months that I dated Becky, I wound up helping her daughter with her homework, taking her shopping, and generally spending time with the two of them.  I knew that Becky allowed her daughter to have a boyfriend – but since her daughter was 13, I didn’t think too much about it … especially since I never saw the boyfriend over at Becky’s apartment.  Well everything changed the day I took Becky and her daughter to the local Six Flag’s Magic Mountain theme park.  Becky’s daughter wanted to bring along her boyfriend, and I said “sure”.  To make a long story shorter, the boyfriend and Becky’s daughter were kissing, making out, holding hands pretty much the whole day at the park RIGHT IN FRONT of me and Becky.  I was seriously concerned about all the heavy petting and action going on between these two kids – and when I asked Becky what she thought about it, her reply was “I want her to be comfortable with her body.”  I thought to myself – “Oh my God, this woman is a retard … and her precious little daughter is going to wind up pregnant at age 14”.  I pretty much had to tell Becky that I just didn’t approve of the kids behaving that way toward one another, and that I thought she was taking a huge risk by being so permissive with her daughter.  Becky’s response?  She dumped me!  She told me that she had started sleeping with a guy from her work, and that she was going to date him.  I was so mad that Becky had cheated on me … but it made me think about how my relationship with her started, and also about the trashy things she would say.  It all added up.  The relationship was doomed from the start, but the sex was outstanding … so the energy was only partially wasted!

Here’s another example of a “false start”.  I met a nice-looking Latina woman (oh – I do love the Latinas) named Virginia.  Virginia was an administrative assistant for a local government official, and seemed to have a lot of the qualities I enjoyed.  She was smart, could carry on good intelligent conversations, plus I was very attracted to her … with her thick black hair, her full lips, and the way she said my name when she wanted me to kiss her, “Grrrregorio …  dame un besito.”  [translates to “Greg – give me a little kiss.”].  Things happened between us pretty quickly … probably too quickly.  As I started to spend time with her after work, I began to notice how bossy she was with her children who were around ages 9 and 13.  Now I’m not saying to not be bossy with children, but I think what I noticed was how she always tended to talk DOWN to them.  Then one evening she started showing me her closets – and how she had everything she owned organized by garment type and color … the whole closet was in perfect order.  Now why would any of this bother me?  Well – people often treat those closest to them the same way … and I could easily envision Virginia talking down to me!  And believe me – that is not what I would find attractive.  Plus – I knew that even though I am very much of a “neat freak”, I didn’t hold a candle to Virginia’s taste … and I knew she would be “on me” – it would be just a matter of time.  So quite suddenly, I decided to bail out on Virginia.  She was so shocked, and hurt – she couldn’t believe that I dumped her.  And I don’t believe I ever told her the exact reason … I believe I simply said that I didn’t think that she and I were compatible in the long run.

Okay – so at this point, we talked about setting some preliminary high-level dating objectives first – then discussed being comfortable, not taking things too personally, watching out for false starts, conserving one’s energy, and being careful at first.  Now we are going to move into several truths that are more related to midlife bachelor operations.  We are going to discuss how to leverage the relationships you have with your female friends, and how to avoid destroying or alienating these critical assets.

NEXT is Fundamental Truth #4 – Female Friends are a Critical Asset which you can also access through the DROPDOWN menu on the top-left of this page.  You can also ADD ANY COMMENTS you wish down below (using our commenting system) OR you might even consider checking out our Midlife Dating Discussion Forum (link immediately below)

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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.