Has either one kinda liked each other or has been jealous? Please help me out here.
Well, bulbapedia apparently has a huge thing for these kind of things (although some of them are just plain stupid).
Really, of all of the connections between Ash and other characters, this is the most widely believed. Ash has the possibility of becoming a pimp if a career as a Pokemon Trainer doesn't work out (and how does thaat work out? In the games it makes sense, but I haven't seen much of an exchange of money for winning battles.)
I don't think it has been confirmed, but everyone knows Misty had at least a crush on him.