“u up?”: when he texts you late at night

Let’s start with something that I hope would be obvious for most of you, but for some reason remains controversial, maddeningly so, even amongst experienced older daters who should know better. If a man you’re not involved with texts you very late at night, asking to hang out that same night, he doesn’t see you as a romantic prospect. Read that again: he does not see you as a romantic prospect—you are already in the “hookup only” category in his mind. He is looking to see what he can get away with.

By “late” let’s say 11PM on, but really whatever time feels right for you, when you would feel uncomfortable if you were in a relationship and you saw your partner getting a lot of mysterious texts. For my math-inclined readers, let’s call it a normal probability distribution centered around 1AM.

Maybe if you were closer, dating seriously, etc, there could be some other plausible intent for contact like this other than casual sex. Maybe it’s a once-in-our-lifetime meteor shower event, and he wants to show you with his at-home telescope! Maybe his mother died at 2AM, and he just needs someone to talk to, and the only one he could rely on was you! But given that you aren’t close, casual sex is vastly more likely his intent. Barring that, anything he wanted to say to you or do with you, he could still do in the wholesome light of day.

 Your best answer, if you are still interested in him, is a cheerfully rested “Hey! Missed your text last night! What’s up?” or something along those lines, THE NEXT DAY. In the (unlikely but not impossible) event that he really is interested in you earnestly, he will still like you tomorrow, and even feel thrilled and relieved when you finally do reply. He will not write you off or give up.