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If you message him casually and just to talk though, he may ask you to go out and do something. If you are hesitant to just come out and ask him to hang out with you, it's a good way to lead him in that direction. Depends how direct you want to be or if you'd prefer he continue to do the pursuing.
She'll own some old rich guy one day. Wow!
But, after I was married, flirting for fun became easy. If I'm not trying to pursue a woman, no "skin in the game", confidence is high and talking and flirting is easy. I find it fun. That doesn't mean there was ever any true intent behind the flirting.
I didn't try to shame her, and I bet she knows it. In fact, I praised her for seeming to have good self-knowledge. I also suggested that calling women "hoes" and thinking of sexual relationships as "games" to be won or lost, scoring or sacrificing points for your gender, was not productive or positive
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