This is how my mind worked when I was a man
Specifically when it came to approaching women, here's how my thought process went:
I listened to women's advice on dating (good), but I categorized every bit of advice into "do's" and "don't's." A "do" would be "I like it when guys are very forward and let me know that they're flirting." A "don't" would be "I don't like when guys open with a compliment about my physical appearance."
However, every "do" was a do for only that specific woman. I knew women aren't a monolith, so just because one girl on TikTok one time said that she likes guys asking for hugs, I shouldn't assume every girl likes that. If a girl doesn't like that and I assume she does, then it's going to end poorly for both of us. Better safe than sorry. Conversely, but by that same logic, every "don't" should be assumed to be a "don't" for all women in general. If a girl says she doesn't like it when guys try to hit on her in front of her friends, I'm going to assume that's a rule across the board, especially if it's a social media post with a bunch of agreement in the replies. Again, better safe than sorry, so all the "do"s are just for those individual women and all the "don't"s are for every woman ever.
You can see why this would limit my options.
Like with location. I didn't flirt with women in the gym because duh, women don't go to the gym to meet dudes. I didn't flirt with women at the mall because women don't go to the mall to meet dudes. Women also don't go to public parks to meet dudes. And by the same logic I should also just knock out work, school, any shopping area, laundromats, their house, my house, a mutual friend's house, bars, inside, and outside. I decided at 17 that I should exclusively hit on women in places that I'm 100% sure they went to that location to get hit on by strange dudes, which leaves literally nowhere.
Not being creepy was really important to me. So every time I heard a story about a woman being creeped out by a man, I made sure never to do the things that guy did. I didn't walk behind any women at night, I didn't compliment women in public, I didn't make eye contact with women in public, I avoided women as best I could in parking lots, and I kept my head down in every social situation.
Keep in mind, this doesn't just pertain to dating. At this time in my life I was wrestling with the feeling that I never fit in with my male peers and I've always gravitated towards female friend groups, groups which frequently rejected me because I wasn't one of them. There were times I wanted to reach out desperately to be accepted by the women in my life but since I carried the social stigma of being a man, I felt like I couldn't do any of that. When I say I didn't "flirt" with women in these locations and circumstances I pretty much mean I didn't talk to them at all because I didn't know what would raise the alarm bells in my brain.
Despite the reasons it proved a unique struggle for me, I've read the message boards, I've seen the comments, I know that a lot of men feel limited in the same way with their desire to flirt. There's no guaranteed way to do it right so it's better to not do it at all. I'm not saying "oh boo hoo men's life is so hard," I acknowledged at the time that women's lives were objectively harder and never tried to claim otherwise and now that I'm a woman I can confirm I was right. What I am saying is that I know how men think, and they're hurting.
