On the Pokémon anime, who would I be friends with? This sounds fun!
Ash: Mainly because he's likeable and easy to be friends with. It would be quite entertaining sharing our experiences of our Pokémon adventures.
Brock: He always seems to have good advice in regards to Pokémon, caring for them and all that. It is also apparent that he cares quite a bit about his friends, a very valuable friend indeed.
The Team Rocket trio. I adore Jessie, James, and Meowth even though they can be a bit annoying. I would hangout, joke around with them, and maybe even help them steal "the twerp's" Pokémon risking getting blasted off lol. I might get a bit annoyed with Jessie and her personality though. And maybe annoyed too at Meowth. He talks too much.
Gary: He'd probably be someone that I didn't like or want to associate with at first, but would end up being friends. To me, he seems to only have a few close friends. That's how I am. I would definitely ask him a bunch of questions about Pokémon research, probably annoying him lol. (If I were in the Pokémon world, I'd be a Pokémon researcher). "Oh wow! You're a Pokémon researcher? So am I! What aspect of Pokémon research are you working on / are you interested in? Mine is friendship evolution! " And of course, I'd have to ask him about Umbreon.