I’m 30, and I’ve had very little success with women. What I want to understand is what happens in the heads of men who seem comfortable with dating. Somewhere between noticing someone attractive and saying hello, I start considering everything that could go wrong.
I’m not looking for a line to memorize. I don’t want a trick that supposedly makes someone interested. I want to understand how an ordinary conversation becomes romantic when the interest is mutual—and how you recognize when it isn’t.
When you see a woman you’d like to meet, what are you expecting from that first interaction? Are you simply curious about her? Are you already thinking about asking her out? I seem to put so much weight on the possibility that I struggle with the actual conversation.
Then there’s rejection. A no sounds manageable when I describe it like that. In my head, though, it comes with awkwardness, embarrassment, and the possibility that other people will hear about it. I worry about making someone uncomfortable, then worry that my worrying will make me uncomfortable to be around. It’s a remarkably efficient system for staying single.
I’m also curious about men who have dated someone they considered out of their league. I know that phrase reduces people to a ranking, but it captures a feeling I recognize: being interested in someone and deciding, before she has any say, that she couldn’t possibly be interested back.
What helped you get past that? Confidence? Experience? Being able to read the situation? And how did you learn the difference between taking a chance and pushing where you weren’t welcome?
I’d like to become less attached to getting a particular outcome. Right now, that sounds good in theory and feels much harder in practice. I’d welcome honest stories from men who remember being where I am. Before you got comfortable with dating, what did you have to stop telling yourself?
