Midlife Bachelor

February 2, 2008
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6) You usually don’t get laid
I say “usually” because I have gotten laid on several first dates – but that is not really the best way to start off a good long-term serious relationship.

7) You have to keep the conversation going
Keeping the conversation going can definitely be a challenge – depending on the personalities involved.  Me – I can talk to just about anyone about just about anything … but others I know struggle to keep things interesting.  I usually try to get the woman talking about herself and her interests (and not talk about myself too much – I hate people who talk or brag about themselves).

8) You have to be entertaining
Talking is one challenge, but talking AND being entertaining is another even bigger challenge.  You cannot talk about religion or politics usually.   And you definitely don’t want to talk about your last girlfriend.  You have to listen to what she says very carefully, and on-the-fly figure out how to entertain her.

9) Watch out for landmines
A “landmine” is a topic that she is sensitive to – and one that if you bring it up will make her either angry or sad or in some way kill the date.  Religion and politics are the most common landmines.  Racial topics can also be landmines.

10) You may have to meet the family
If you are picking her up from where she lives, you may have to meet her children, or possibly her parents.  You have to be extra nice in such situations – and roll with any odd punches that may get thrown your way.

Really the best way to know if that first date you just went on really did suck was how you would answer these two questions:

  1. Do you want to go out with her again?
  2. Did she agree to go out with you a second time?

If your answers to both of these questions was YES, then your first date did not suck.  Otherwise, your first date did suck, and you have “joined the club”.   The only thing you can do is learn from what happened, and try it again with someone else.

If you are a midlife bachelor, and ALL of your first dates seem to suck – then you could probably use some help from other parts of this website.  Check out the section entitled, The Midlife Bachelor Personal Makeover – which will help you fine tune both your appearance and attitude.  [Even a Ferrari needs a tune-up once in a while – and so might you.]   You also might consider reading the section on Develop a Strategy for Midlife Bachelor Success.   The more thought you put into your own personal dating strategy, the more likely you are to succeed.   Good luck.  First dates suck!!!

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