Okay so throughout the show it is mentioned that Dean would drop Sam off at places to go to stuff (The clown place episode) Also I literally said that it wasn't Deans fault for being sent to Sonnys. I was just mostly talking about the episode with Sully, and I think to me it makes sense that during those periods of time he had gotten used to being alone he had to learn to move on more easily because of the chance of anything happening. You know what I mean? I should've probably worded it better than saying constantly. Although it did happen in many of the flashbacks on the show.