It's not that hard, dude — and I say that being nontrivially Aspie, and profoundly bad at these kinds of social cues. The point where it becomes "unacceptable"

It's not that hard, dude — and I say that being nontrivially Aspie, and profoundly bad at these kinds of social cues. The point where it becomes "unacceptable" is subtle and situational, but not terribly ambiguous. A good generalization: presumably, you like this person. Why would you want that — or you — to be a thing that is unpleasant for them? That should be the place you're operating from: what's good (or, at the very least, not bad) for them, not what you want out of the situation. That said, here's a few tests you can use: If you have any kind of authority over the other person (or them over you), don't even start. If it's unwelcome, stop immediately. Apologize if it's warranted. Go out of your way not to make it worse. If you're in any kind of doubt about whether it's appropriate or welcome, it probably isn't. Err on the side of caution. If you still want to try, a good place to start is probably an honest, respectful, "Hey, so I think I've got some feelings here, but I don't want that to be a problem for you." If you do that and you're told it's not OK (whether explicitly, or implicitly, thorough the lack of an enthusiastic response) DO NOT UNDER ANY CIRCUMSTANCES CONTINUE, unless that response changes. "Unless that changes" doesn't mean polling for state changes. That's creepy. That's all I've got, offhand. This list isn't remotely exhaustive. It's survivorship bias, but I've never been sued for harassment, nor my employers because of me. And, like I said, I'm not good at this stuff. (This comment was edited bigly.)