Drake - James thinks that relationship is strange. He just does not understand, which is his general not being able to understand relationships. Since he is friends with all the assholes, he is probably friends with James, lol.
Vivi - Love the name of the tavern. Seriously. I am not sure how much he likes coldly polite, so I don't know how much he is in there.
Jareth - James is cool with being hated. He kind of prefers it. Also, he prefers animals to people, so he has no problem with Cat.
Aisling - Hmmm. Monthly fight ring. I have no idea whether James is approachable on that or not since he's in the FG. Considering his history - which he does not advertise or talk about, but also does not hide - he could be a good candidate. Though, to be honest, he would likely want to get into it to try and shut it down. (Though he will secretly enjoy the fighting.) I'm sure that's not a line you're interested in, but just throwing it out there.