Thomas is pretty open to most opportunities. That said, I think if he moved into the neighborhood that Thomas came from that could be a good way for them to know one another, he would have known Thomas when he was starting out so he would be more likely to be friendly with him.
As for Ottiley I think they could know one another from either the Orchid Lounge (if you think he'd go there) or just a random meet up. Drinks and bitching always on the menu.