Bite me

The past few years I've become much more sarcastic and, eh, almost mean but it's intended to be playful. Almost everyone gets that. Actually, most everyone throws it right back at me and we have a good time. This is now a part of who I am.
How the heck am I supposed to get the idea that someone is irritated if they play along and act like a friend? It's lame and I feel like a jerk for acting like a jerk but I didn't know he thought I was being a jerk. The whole beating around the bush thing, when things aren't said straight up make me feel like I'm back in high school.
I feel lame and I think this situation is lame.