Develop a Strategy for Midlife Bachelor Success

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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.