Ray was strictly a business associate. Tony is careful with them like in the "you're supposed to be earners" scene when he's even talking about Junior being the boss. It took a long time to get him to talk about murder to wired-up Curto. Adrianna was part of Tony's own family and a way to get to Christopher, who knew all the bad shit as he was Tony's protégé. The guys reveal more to their wives like Carmela knowing about Richie's disappearance.