I think that a person just needs to be willing to fail at their wit every now and then but then again maybe don't swing for the fences with people being as sensitive as they are these days. I sometimes think about the things I used to say to mostly girls when I was in my early 20's and that sort of stuff really wouldn't fly today. Times have changed, that's for sure.
The last time I was in the States I was warned by some friends about how "you can't say that" about a lot of things. I wasn't even being offensive in my own eyes but according to them I was out of line. We aren't so sensitive over here... not sure exactly what changed.