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?

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    64 months ago

    my younger brother is like this lol. we have a really good relationship, but he’s a busy person and sometimes a text message, even an invitation to something, will go completely unanswered, but we’ll have an entire conversation in the same thread the following day.

    sometimes I’ll send him a text that is an invitation, and part of a different conversation, and sometimes he just responds to the conversation part and completely ignores the invitation side. I’m not entirely sure what’s going on there, but it’s not unusual.

    try inviting him to something different. bowling maybe