Midlife Bachelor Strategy - The First Date with Any Woman

Develop a Strategy for Midlife Bachelor Success

Step 2: Conquer the Basics and Start Dating
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The First Date with Any Woman
Maybe some of you midlife bachelors reading this section think this is all an unnecessary discussion. Perhaps that is true for you – or perhaps you might consider it a good personal refresher course. Maybe your skills as a gentleman could use some polish? Maybe not. If you truly feel this is boring you – then please skip ahead. I think it is all very valuable – it never hurts to hear input from someone else, right?

Okay – you’ve got the woman to agree to the first date, and all either of you know is that it involves a meal, for example. First be sure to confirm the date ahead of time. If you asked her out more than several days in advance, be sure to call her the day before and verify that you are still ON. If you have to leave a message, that’s fine – just be brief:

     “Hi this is Greg, and I just want to make sure we are still on for dinner
      tomorrow night.   I’ll pick you up (or meet you, if that is how you left it)
      at X:YZ p.m., and we’ll go from there, okay?   Call me back and let me
     know.”

Of course, you are now stuck with having to leave your phone number – so cross your fingers in this case.

Several things to remember prior to picking her up for that first date:

     1)   Dress appropriately for where you are taking her
     2)   Keep all of the basics that you learned in The Midlife Bachelor
           Personal Makeover in mind
     3)   Be on time – this is really important. If you are running more than ten
          minutes late, then call her and let her know what is holding you up.
            Women HATE to be left waiting.
     4)   Have reservations made for where you are going, if appropriate.
     5)   Make sure your car is clean or reasonably clean. No one wants to
           date a slob!

When you pick her up for the date, or when you meet her somewhere:

     1)   Tell her that she looks nice (assuming she does, in fact, look nice).
     2)   Be a gentleman.   This means different things to different people.
           For me, I am the type to open doors for a woman.
     3)   Don’t go overboard on the gentleman stuff. Don’t try to order her
           meal for her, for example.   Try to be considerate, and stick with
         all the basics.
     4)   Keep in mind the conversational suggestions from the Midlife
         Bachelor Personal Makeover section.   Don’t talk too much about
           yourself, and try to get her to talk about herself. Try to figure out
         common interests based on what she tells you … in other words,
         LISTEN to what she says.
     5)   Don’t look at other women, or be flirty with the waitress.   This
           is just common sense, but some midlife bachelors don’t know
           any better.
     6)   Plan the date loosely, and allow for spontaneity.

If your first date is going well, then time will seem to pass quickly for both of you. Keep in mind that even though you might be having a nice time, she might not be for various reasons. It might be something you said or did or didn’t say or didn’t do. Hell – you might never even know why she didn’t have a good time … it might not even have anything to do with you. [For example, she might feel bad about going out with you because she recently broke up with a boyfriend that she really cares about.]

Watch for Signs or Signals on the First Date or Two
You’ve got to watch for various signs that she may be giving you which can signal how the first date is going from her perspective. For example, if she looks at her watch or cell phone frequently – that typically means that she thinks it is time for the date to end. If she looks bored after a while, and stops engaging you in conversation – that is also a signal that the date should end. If she comes over, and sits in your lap and starts kissing you – that is a sign that the evening is going great, and probably just getting started. Everything is situational – there are countless signs that she could give you. Don’t be overly analytical, and don’t necessarily call out what you think you see her signaling … but do keep your eyes and ears open, and try to act appropriately. For example, if you notice her constantly looking at her watch or cell phone – you could ask her something like, “Is it time to go?” She might respond with something you are not expecting – like she is concerned about her children with a new babysitter … and that is why I say it is best to not be overly analytical.

Positive signs or signals a woman gives you can be sometimes be either subtle (hard to detect), or sometimes they can be really overt or obvious – it all depends on the woman, and also on how comfortable she is with you. Usually women will become more comfortable with you the more they see you – so don’t necessarily expect her to fall for you immediately. I’ve found that if you listen very carefully to what a woman is telling you, you can pretty much gauge where she thinks things are going between you. If she hints at going somewhere you can be alone, then you can guess what she might be thinking. If she talks subtly or not-so-subtly about sex – you can bet that sex is on her mind, and that you might just be getting lucky sometime soon. The look – I’ve found that women who want to either make-out or have sex will almost always give me what I call “the look”. She just looks right at you in a very distinctive way. Not like you have a zit on your nose – but more like an extremely attentive eye-locking stare. To me this look is unmistakable. You will know when you receive this look. If you are on a first date with a particular woman, you might not get this look until you are telling her goodnight – or you might not get the look at all. If you don’t get “the look”, don’t take it personally – sometimes women take a while to warm-up to you. Or sometimes the chemistry just isn’t right for both of you. There is no right or wrong – it is just what it is.

Next >>> Saying Goodnight or Goodbye on the First Date or Two