Know when to Talk and When to Listen
So far in this section about midlife bachelor attitude adjustments, we have talked about being a positive person, recognizing and coping with personal insecurities, and also some of the ruts we can potentially fall into.  Now I want to take a little bit of time to focus on the mechanics of how you interact with a woman you are just getting to know … and hopefully trying to get a date with.  I assume that your appearance is great, and that all other aspects of your attitude that I’ve previously discussed are either polished or carefully hidden.  Assume you are now in front of the woman you are interested in – and that it is just the two of you.  There needs to be conversation, and it doesn’t hurt to have somewhat of a strategy in terms of the overall flow.  I’m not going to tell you what to talk about – no. But I am going to give you some basic pointers based on what I’ve noticed with respect to my own initial interactions, and also what I’ve noticed with other people.  Here is what I recommend.
Get her talking about what she is interested in.   Women love to talk about themselves, and what they are interested in. My recommendation to you is that when you find yourself talking to a new potential date – that you focus on asking her questions about herself, listen to her answers, and then talk about how you can relate to what she is telling you.  If you do this, the woman will believe that you are truly interested in her as a person (and not just her boobs).  She will also think that you have common interests – and that you listen to and care about what she says. This approach will help endear her toward you, and will increase your chances of getting a date with her, etc.
Of course, there has to be an element of reality here.  You DO have to be interested in some of the same things that she is … otherwise you are lying to the woman and/or to yourself, and setting the relationship up for failure.  A good example of this was when I was on my first date with that hot Latina electrical engineer named Trish that I wrote about earlier.  Trish explained to me that she was very interested in tattoos, and that she had a very large tattoo on her ass, and that it extended to her leg and also her lower back.  I remember pretending that this was interesting to me, and asking her to show it to me – which she did.  [Actually I just wanted to see her ass, and it was fantastic – tattoo or no tattoo.]  I thought to myself that her tattoo was the tackiest thing I had ever seen on any woman – but I didn’t tell her that.  Instead, I went out with her again – and later let it slip that I thought oversize tattoos are ghetto.  BOOM – relationship over with.  Actually – it was not a relationship, as we had only gone out a few times and had not had sex.  My point – if you are not remotely interested in some of the same things as a woman, or if you find some of what she is telling you to be a complete turn off … then it is best for everyone if you cut your losses, and move on.
Don’t talk too much about yourself. The easiest and fastest way to turn a woman off is to talk non-stop about yourself. I’m not saying that you should intentionally withhold information – no.  Rather I’m saying you will be better off if you prevent yourself from rambling on and on and on about you, and things about you.  You will bore women to death – and create the impression that you are self-absorbed.  Be strategic about what you say about yourself – and don’t sound like you are God’s gift.  Women generally like men who are humble.
My buddy, Mike, is by far the best example of talking about himself too much. Not just to women, but to everyone!  If you spend twenty minutes with the guy, you will know exactly how much he is worth, what real estate he owns, what his overall investment portfolio consists of, etc.  None of his friends are sure why he always does this – but he is as predictable as the sun rising each morning.
Whenever you have your first real one-on-one conversation with a woman you are interested in – by the time the conversation is done, you should be able to answer these questions:
- What kind of person is she?
- What does she do for a living?
- What does she like to do, and what are her interests?
If you cannot answer at least those basic questions, then you either did not listen (bad) or spoke too much about yourself (worse).
