I feel your pain Pike. I've been raised on deadpan humor so the results are very mixed. Friends that know me really well get off on it, and the occasional stranger will enjoy it as well.

Otherwise, I end up using it in social situations, and the results are almost never good. In one instance, my friend introduced me to a group of guys he knew from high school. The conversation went pretty well until I said "you guys are a very, very attractive bunch" with a straight face. I'm honestly not sure what I was going for, and they honestly were very attractive, but I was met with (understandably) very strange faces and an "..Okay, so anyways we gotta go...".

The worst part is that I think I function pretty well socially. Everything goes fine until that inevitable horrible joke or comment that never works out. I end up monitoring my thoughts around people I don't know, but that in itself just makes things strange enough. Lose/lose situation until you find people that enjoy it, I suppose.