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?
Usually I stop after 2 or 3 attempts.
You could also ask him directly. Maybe he's generally not interested in lunching together, or he was just too busy to respond, or whatever. These questions can be awkward, but also deepen a friendship. A risk-reward mechanic in the game of life.
You can't harm a friendship by talking about it, but you can save yourself some time by finding out it's not working out earlier than otherwise
Right, that was the spirit. Though to be honest, it can harm. Some people are shy. Or strongly shy away from awkward situations caused by not-yet-close-friends. They can still be great friends, but unlucky situations during the getting-to-know each other phase can prevent that. We judge people with different standards, depending on how close they are. So when you interpolate distant-behavior to predict close-behavior, there is probably some error margin.
So there is some risk involved in asking, but likewise for not asking. I guess just be you and see where it goes.
One final thought: I think it's important to take care that the question is not perceived as an accusation.