In the few manuals that I read, as well as on this forum, I've never seen mentioned issues of social awkwardness, in particular in speech.

To me it happens not when I have in mind what information I want to communicate (like which coffee I want at the Starbuck's, or how noisy my roommate is, or why the government sucks), but when I have in mind the kind of vibe I want to communicate. In this case it feels like I know what goal I want to achieve (be funny, be sarcastic, be compassionate), but I have no idea how to get there, and it becomes a hit-or-miss.

For instance when I'm with a girl the conversation would be flowing and at some point I'd have this message scrolling through my head: "Insert a joke here." I then have about 3 seconds to make up a joke based on the context (so as not to leave too big a hole in the conversation), sometimes it's funny and the girl laughs, some other times the second I utter the words I realize it's offensive or awkward.

Has anybody been there? Any suggestion on how to deal with that kind of problem?

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