Well, the Experience (where his mother works and he hangs out a lot) is right next to the Casino. As is the strip mall where the Boom Boxxx is located (where he works). I think he probably spends a little time at the Brothel, too. Which is secretly located inside the casino. So, yeah, they have different circles but they're pretty close together. I think they'd either run into each other at the Casino or in the immediate area surrounding it.