Well, bulbapedia apparently has a huge thing for these kind of things (although some of them are just plain stupid).
http://bulbapedia.bulbagarden.net/wiki/Shipping:Pok%C3%A9Shipping
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.)