I even find it vaguely intriguing that Sam would take a back door into wanting stuff out of life again, that he'd get to it through feeling that he'd lost everyone and had no anchor and would fall back on the last thing he had really been able to want. There's been a lot of fatalism and acceptance about Sam the last few years, and this seems like sort of a positive version of that. But it's hard to get around the Dean thing, and hard for me to believe that he wouldn't have a boatload of issues surrounding romance.