NYC dating etiquette — did I fumble by not talking to her on the train

💖 Dating

Last night I was on the train pretty late after a night out. There were two girls near me, and throughout the ride I kept noticing them looking at me in my peripheral, talking to each other afterward, and occasionally one of them and I would actually lock eyes. It happened enough times that I started wondering if there was some interest there.
I considered saying something, but I was a guy by myself and it was two girls together late at night on the subway. I feel like approaching women in NYC can be a difficult line to read. Obv I don’t want to make someone uncomfortable if I’ve completely misinterpreted a few looks. At the same time, there’s still this expectation that the guy is usually supposed to make the first move.
Part of my hesitation was also the fear having an innocent approach taken the wrong way. Nowadays, with sensitivity around literally everything, I would rather be overly cautious than make someone feel uncomfortable, especially on public transportation.
The funny part is we all ended up getting off at the same station they left ahead of me first. Once we were off, nobody said anything and we eventually went our separate ways.
Now I’m wondering if I fumbled what could’ve been an opportunity lol.
For New Yorkers, especially women: if you’re repeatedly looking at a guy, talking to your friend, and making eye contact with him, would you be comfortable with him saying something? Or is the subway basically a “don’t approach” situation regardless?
And once we were off the train, should I have just said something? I also figured if she was interested enough, she could’ve approached me too.
Curious what the actual NYC etiquette is because I genuinely couldn’t tell if I played this correctly or completely fumbled it.

Posted Aug 14, 2026, 5:47 AM UTC

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