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My question is why are so many women in this area so immature when it comes to men and dating. I often here them complain that all the good men are gone and its so hard to meet a good looking man who is also caring and compassionate when it comes to others. We believe that our friend was and still is in love with Kim. I heard some good things about her and want himn to find the happiness he deserves. Can anyone offer me any advice to pass on to our friend Bob?
I suspect the only problem with your friend Bob is that he doesn't know how to "play the game" that seems to be the socially accepted method for meeting women in our area.
Plain and simple: Most local women (at first) like the guys who treat them the worst. Granted there are the "few" who are most old fashioned who don't play these games, but by and large most women are this way, although they won't admit it, or even claim the opposite. They don't want the guy they know they can have. The fact that Bob is going the conventional honorable route and that isn't working tells me that this woman is not the old fashioned type and has been conditioned by our local society to like the "bad guys".
It's a shame because Bob may have blown his chances already. Sadly, Bob needed to instead find out the type of guys that her and her friends admire, and be one of them. Note that this is probably a totally different type of guy she "Says" she wants, she herself might not even know she's doing it.
I know this is sad but that's what people are like nowadays.
For starters, he needs to stop holding open doors for her, offering to buy her coffee, all those sorts of things. Matter of fact, if I were Bob, I'd purposely make efforts to do the opposite, like leave just ahead of her and purposely and clearly NOT hold the door for her. When she asks questions, say things like "whatever" and blow her off. Doing "nothing" is not enough.
He needs to look selfish, kinda like smoking a cigar that bothers others and not caring about it, or having a loud motorcycle because "he" likes it and he couldn't care less what others think. Makes him look strong, independent, and strangely successful. Hard to describe, but that's what Bob needs to do for the type of women that don't like the sincere honest approach.