Jane Espenson, Battlestar Galactica and Buffy writer, on a joke she once wrote that failed:
Sometimes you think you’re being perfectly clear, and you’re not. I once wrote a line for an episode of Buffy: Xander, using whimsical phrasing to convey that he thought someone was crazy:
Spike may have gone to the land of the twirly hand gesture next to the temple, but he was right…
No, really. I thought it was clear… And then we were on stage, shooting the scene, and it suddenly became clear to me that no one had the slightest clue what I was going for.
In the end, they made the joke work in a different way:
…in the moment we ended up playing the incomprehensibility of the line. Xander says it, everyone stares at him, and he makes the gesture. It’s not exactly the joke I intended, which was supposed to be swift and smooth, but it works fine.
The point of the story is that moment of realization: I’d written a joke that was totally opaque, and no one pointed it out because they had no reason to even think there was a disconnect.