My bad social habit which I am working on correcting is in imposing a thought on someone's personal life a bit too eagerly, which for me usually begins with the phrases, "so then it's like..." or "you should..." - I got caught out on the former phrase just today, in fact. When they take offense it's always a blow to me since I don't want to be That Guy, but I have to admit that I get the same sense that people I really click with don't even bother taking offense at that stuff. They're okay with having a conversation that has some conjecture and vulnerability, and some difficulty of thought conveyance, built into it.

Conversely, I get a really bad impression when the defense mechanism rolls out, particularly so when it's elaborate, practiced, and snarky. A strong rejection indicates that I've tread into territory they'd really want to not dwell upon. Extreme snark is even worse since it indicates that their intention is to control the power dynamic. The time I encountered that, I found myself boomeranging it by replying "I'm too trusting."