I did this because I can. =D
Rich -- Charlotte: This I see going very smoothly. End to End, they could be fast friends that could find a deeper connection if they talk enough. And he mostly sticks to softer types of rock. (Think The Fray, 3 Doors Down, Gavin Degraw, Jason Mraz) However, he has no issue busting out a little Ray Charles and other genres. So I think they will be a-ok.
Rich -- Enrique: I feel like they might clash over the snobbish behavior and also if he belittles working class people in front of him. He would however respect his life in the modeling industry. Rich has done enough research to know some of the crap models deal with. So I think they could have a strong friendship but certainly nothing soft and gooey type of bromance. Perhaps they could, if they end up making it a thing where they give each other crap just to mess with the other.
Rich -- Riley: Oddly enough, I think these two and get along very well. He will most likely see her as "one of the guys" sort of thing. They can end up very close. I can totally see him ending up with funny feelings about her. Perhaps some confusion could be good for him in this city. As for the old friends idea: Yes. =)
Rich - Hazel: I can see a rough start coming off with this one. With a cold reception, he might just wear metaphorical coat around her. Once they start to move past that first wall, however, Rich will be a big fan of her kindness and wouldn't mind doing activities. This one could be interesting.
Rich - Shane: This one could go either way. It just depends how they end up interacting. Because, they both have a bit of a rough past (that I will reveal in the rp, I promise.) If they can get to a point they can have a heart to heart, that a true friendship can be formed.