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If I could just talk with her alone at a coffee shop for an hour I know I have an excellent chance of wooing her. I can't knock on her door at random and ask her nor can I do it during dinner time. How should I approach her?nGaryn Hi Gary,If you don't want to ask her out in front of others, then you'll just have to think up some plan to break her away from the crowd for a moment or two. Maybe using a buddy can help somehow?

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***QUESTION***

"David,

I am a 39 year old guy and am still single because of a lot of personal problems I went thru in the early and mid 1990s (nothing too serious--wasn't arrested, didn't go bankrupt, wasn't psycho, etc). Now that all of this is in the past, I've been venturing out into the dating scene again. As I'm more serious about finding a relationship, I prefer women in their 30s and early 40s. My question is this: Do you think that the "cocky and funny" routine works on women in their 30s and 40s too? It seems to me that women of this age group who are divorced/single do not want to play games as much. I'm not looking to play games either.

Or should I take a modified approach to cocky/funny?

Thanks,

Dating in Chicago"

***MY COMMENTS***


You're using the word "games" here to describe the cocky/funny attitude, and I think that we're mixing up our definitions and associations. When I think of "games" as the term relates to men, women, and dating, I think of things like lying, cheating, and manipulation (in the negative sense).

Cocky and funny is a fun, attractive attitude that is VERY attractive in general - to women of all ages.

And yes, women that are in their 30s and early 40s love it.

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