Weirdest fleet is a tough one - most of the time, at least a few folks are pretty drunk, so the conversations are fun. Let's see ... I've been on a few fleets where folks have gotten into screaming matches with their spouses, which tends to be awkward until somebody finally mutes 'em. I remember a fleet where we were working with some Russian folks who didn't speak English, but the corp had someone who spoke both Russian and English jumping back and forth between channels to coordinate. As it turned out, there were a few things lost in translation, so we all wound up dead I've also been in some fleets where the opposite is true: 90% of the fleet (including the FC) only speak e.g. German. After being in a few of those fleets, I learned "jump", "hold", "s**t", and "idiot" pretty quickly.
For drink, I would say Coke. I might add whiskey if something expensive just melted into pixels.
On a kitchen sink roam, I like 150mm rail cormorants. They're cheap, quick, and can catch lots of stuff with some targeting scripts. I've also done pretty well with rapid light Caracals, and Omens are fun ships to take out just to see what happens.