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?
Yeah, making guy friends is hard at this age, because it's considered weird or needy to show interest in another man. That's why it helps to have a shared interest or hobby. Some men feel uncomfortable "going to lunch" or "going for coffee" without an agenda, because it feels like a date. It's much less awkward to "go out for a beer" or "go watch the game" because those are socially acceptable man dates.