A friend just sent me this link and oh it's such good advice:
https://whatever.scalzi.com/2010/06/16/the-failure-state-of-clever/
In short: The failure mode of clever is “asshole.”
Meaning, if you're trying to be witty or clever without context (like, the first DM) with someone who doesn't already know you very well, well, don't.
It'll likely get taken the wrong way, and that's a far worse outcome than your first interaction being polite and to the point - the wit can shine later :)
(I have definitely fallen foul of this many times!)