I used to feel like I wasn’t enough for anyone. These days, I know I have worth, and I can be alone without treating it as a verdict. That’s real progress. It just hasn’t made asking someone out any less confusing.
I’m 25, and every so often I approach a woman I’m interested in. Sometimes she’s a coworker or a classmate; sometimes she’s someone I meet in public. So far, those attempts have ended in rejection. I can accept each person’s answer. What gets harder is looking at all those answers together and having no idea what they mean.
My looks are the obvious thing to question, partly because they seem like something I ought to be able to assess. But I also wonder whether I’m still carrying more insecurity than I realize. Maybe an approach feels awkward even when I think I’m doing okay. Maybe I’m reading interest into ordinary friendliness. My record certainly hasn’t given me much confidence in my ability to spot a signal.
Then there’s the practical side. I live with my family, and when I imagine dating going well, I immediately run into the question of privacy. I don’t have an obvious place in mind if things become intimate. Sometimes I get so far into that problem that I start wondering why I’m trying before I’ve even arranged a date.
My schedule gives me another reason to hesitate. I work, study, work out, and am building a startup. I can tell myself there wouldn’t be time for dating anyway. Still, I think I could make room for a few casual meetups.
I don’t need every woman I ask out to say yes. I’d just like a better sense of what’s happening when the answer keeps being no. Is it my appearance, the awkwardness, the signals I’m missing—or something I can’t see from my side of the conversation?
