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I have been amazed that some of the scuzziest looking bums think they're God's gift to womankind. They act like they're doing a girl/woman a favor by making a pass at her, when no woman in her right mind would be interested in the guy if he were the last one on earth.

I knew a guy who you might consider fitting that category. Overweight, not well educated, starting to lose his hair. He flirted at every woman who looked interesting. Most women were repelled.

Why did he keep doing it? Because it worked for him!

Yes, most women were repelled. A significant percentage were not. So he always had female companionship.

A technique with a 95% failure rate is still viable if you're not investing that much time and effort in the failed attempts, as you quickly sort through the women who are not going to be interested in you in order to get to the ones who will be.

Rather than being on his best behavior, and spending a lot of time on a woman before she decided he wasn't for her, he made no attempt to mask who and what he was, but didn't spend more than a few minutes on a woman before deciding whether to move on. In the process, he left behind a bunch of women who thought he was a jerk. But he didn't care, because he was carefull to do his flirting away from work, so it didn't matter what the women thought of him afterwards

I was thinking more of along the lines of the dirty, smelly, toothless welfare bums that were prevalent where we used to live. They had the attitude that was described, that of being picky and thinking they were God's gift to women and were entitled to a knock out, or that a knockout would even be interested. They still found someone but ugh... You're right though. Even 5% is enough of a return to encourage the guy and keep him going. That guy you knew sounds a lot smarter than most people would realize, lack of education not withstanding. He wasn't deceitful, and he did it where appropriate.