When I was in my mid-twenties I attended a singles mixer in San Francisco, held outdoors on a pier. It was a frightening place for a shy person. One very Dilbert-looking fellow (literally), in a brown leisure suit, went straight to the outdoor bar and started ordering stiff drinks. I watched in awe as he chugged one after another, trying to find some social courage. Unfortunately he reached the blackout point before he reached the witty and charming sweet spot. I happened to be looking in his direction when he started to topple, like a diseased redwood tree. He was probably unconscious before he hit the pavement because he never used his hands to break the fall. It was a full-on face plant in cement. I didn't see him move again, even after the emergency crews arrived, although I assume he recovered.
Anyway, as the emergency crews worked on him, right in front of the outdoor bar, while the assembled crowd watched in horror, I walked up to the bar and said in an overloud voice, "I'll have what he had."
This witticism did not go over as well as I hoped. The bartender went into full legal defense mode, explaining that the fallen gentleman must have had many drinks before he even showed up. And none of the single women came up to me later and said anything like "That was very witty. I must have you." It was one of my more inappropriate moments.
Tell us your most inappropriate witticism. What's the worst thing you ever said out loud?