He possibly would, only with a little more self-esteem. *lol*

I can see him going to college, and having a not so close relationship to Sam. Friendly possible and less "You ruined my life and I hate you!" like from Sam's side, but definitely not that close. And I can see them not hanging out much together with each having their own circle of friends.

And I think Dean would probably be married at the age of 25 or something :-)