I guess you guys call it AMOGing or something? Anyway, there's a guy in one of my social circles that says some pretty off the wall shit to try to bring me down in front of women. I don't think he tries to do it on purpose necessarily, and I normally manage to make him look like a dick for it, but one instance in particular fucks me over every time.

My sense of humor is a little over the top sometimes, bordering on becoming offensive. Think of a Daniel Tosh sort of humor. Just like Tosh, I can get away with it by wording things carefully enough so that no one really hates me for it and following up with a slight grin. But this guy always ends up saying something like "That's not even funny, don't joke about that" and it kind of changes the environment of the conversation to where I look like an asshole.

Any tips on how to respond to something like that? I'm starting to notice a lot of guys, even friends, have been trying to do this kind of thing to me lately.

Couple of things.
1. Mysteries Amog tactic, Ignore or say "cool" and move on with your conversation. Act like he isn't even there. This is great because it will piss him off even more without you even doing anythings.

2.Have clever respond. Don't be afraid to take things to far. Remember, he starts it. If he calls you out for taking things to far, say,
Somewhere along the lines of:
-You start, I finish.
(these 3 lines, treat him like he is a 5 year old kid that got offended and your calming him down, while you say it. Take it to the absurd, it will be hilirous)
-Your not gonna tell your mother now are you?
-your not gonna cry now are you?
-I am so sorry, lets go out for ice cream, my treat.

Hahaha, I love the line about the ice cream. I will definitely be using that. Thanks for the reply.