The confusing thing is it’s not a gradual thing of them losing interest. It’s very fast. Like something is just “different” one day out of the blue. I had one girl break it off with me because we were talking about sex and she said something about liking to be tied up. I said I don’t like to be tied up, I like to be in control. She later told me that made me sound like a prude and dumped me.lol It’s not something drastic I’m doing, they’re taking one small thing and nexting me for it. I haven’t found that older women are always looking to get settled down and all that, they sure aren’t pursuing that with me. They just seem to be dating around, doing these 4-5 dates with a guy and move on because they will tell you stories about guys before and the same 4-5 dates happened and something ran them off.If your friend is genuinely unattractive he may need to persist more than the average guy. He has gotten laid by sacrificing his dignity, integrity just for sex.
Men can pursue, up to a limit. The issue is when you are pursuing and the lady isn't reciprocating and you're still pursing to change her mind.
If you went on 4 or 5 dates, it means the woman was interested, at least initially. It's okay to pursue interested women! In those 4 or 5 dates the woman has changed her mind so its something you've done to make her feel different about you. Also as you get older a ladies priorities change, they are looking to settle, get married, have children etc, so you can't employ the same game.
I know what you mean, you need to get better at assessing her true interest. This is part of your self development.