I have a rule of thumb. I’ll try three times to make plans with someone else without a definite response. After that, it’s up to them whether or not to do something. For instance, when asking someone out if I get three non-committal maybes, I won’t bother to ask the person out again. If they were secretly hoping for a relationship but were following some set of advice that says to play hard to get, it didn’t work. Or if they are just too busy to carve out an hour to hang out, I’ll know their time management would annoy the hell outta me if we were to date. This rule of thumb applies to making friends, business relationships, etc.
Any kind of definite response triggers the end of the rule. A no is obviously a no and I’m not going to pursue it. If the answer is yes, obviously the rule no longer applies. If the answer is something along the lines of
I can’t do X, but how about Y that also counts as a definite answer.
It’s important to remember this is a rule of thumb, not something I apply rigidly. It depends on the person and the level of relationship I already have with them. But as a rule of thumb it keeps me from wasting my time.
Sometimes people just have to say maybe or cannot commit to a plan. But after three times it tells me they have a fundamental problem (perhaps justified) with being up front. It’s pretty demoralizing to keep chasing something while being strung along. I refuse to be strung along.