Yes, there were a couple of times when Leo kept asking about his family. I think that's because Leo knows what happened to Dylan in the past and it probably has something to do with them. Leo encouraged Dylan to reach out to his family. Whereas Samuel's main motivation is to get Dylan to come out when he's not ready.I’m not sure about that. Like maybe I’m remembering wrong but i felt like Leo was quite pushy and refused to respect boundaries. Like when Dylan makes it clear that he’s not comfortable talking about his family and Leo pushes on repeatedly despite that.
The morning after at breakfast with Michael and that girl, it probably didn't go as bad as Dylan thought it would, but on some level, it has already changed the relationship between them to the point where he is covering himself up in the showers, when Dylan is present, and he's never done that before.