No, I think Sally would be better off with a GM who is interested in helping her achieve her interests within the game, then stay in one with a GM that has arbitrary "must be this tall to ride" standards.
I’ve spent five years as a stand up comic, maybe 15 as a decent dungeon master. I've been paid for writing comedy modules. I’ve been on the set of comedy TV shows, I’ve listened to thousands of hours of comedy podcasts…
I have no idea how to make someone quippy. You can tee someone up to be funny; Zeppo Marx, Michael Cera, Christina Applegate in
Anchorman… Lauren Lapkus’s show “
With special guest” varied week to week if she or the guest would be playing it straight. You can give people suggestions, act credulous, take them both literally and seriously. You can follow the trail where your partner is going and ask what 1000-year-old man did when he met Moses. You can't inculcate a quip.
Some of these suggestions are utterly ridiculous. The idea that everyone comes up with the jokes beforehand is bizarre. The idea that the GM would come up with the jokes beforehand is wild.
Someone accidentally came up with the best idea, write a bunch of jokes…
But you should randomly roll for the punchline and make the player sell it. Someone just lost their daughter? Oops, that’s number 15, “
that had to hurt!”
The mayor believes only the heroes can solve the case, because the Avengers are busy elsewhere? Number 15,
"That had to hurt!"
Maybe make them all that one. Worked for "Clobbering Time."