cross-posted from: https://lemm.ee/post/38443030

I’m a man in my 40’s, moved to a new area and trying to make friends. A guy I’ve had lunch with a couple of times and we’ve connected pretty well. I’m not getting disinterested vibes when we’re actually at lunch. However, I’ve invited him to lunch 3 times recently, once each month, and he’s not responded. He’s responded to other texts. “Hey, I’m going to event XYZ, any advice” and he’d reply. I’ve run into him at the grocery store twice in that time period and he’s been genial. He’s never offered/initiated lunch or anything, but that’s not new. (No one ever asks me to do things, I’m The Organizer.) I’m getting really, really mixed signals.

How many more times do you try in a situation like this before you “take the hint” and stop?