It's a big bomb to drop all at once. Letting Dean take it all in, Sam lets silence linger for a few moments for his words to let his brother soak it all in. In fact, there's parts of it himself that he needs to come to terms with. There are no guarantees that everything will go his way. Ruby could refuse the proposal, just to start with. Yes, he absolutely could choose to end up with someone named Karen. He wants to believe it'll work out but he has a healthy understanding of the risks.

Hope is what he needed to hold on to. His brother's doubt didn't change that but it helped sober a fraction of any delusions that still lingered. He nods, pulling his lips into a line. "I might never get my memories back. Yeah. Everything from the time I was born to when I leave here... Just everything. There's no two ways around it," he clarifies for Dean all in one breath. Of course he's still on the fence because of what Dean might say as he realizes this affects their relationship the most. The complicated part comes with that he's already made up his mind subconsciously deep down. He knows he needs Dean on board (just as he needs Ruby to want it too) first even if that takes time.

He makes a face at Dean's next statement about the imaginary new family he could come back with knowing. "Honestly, I don't want to think about that. But if that happens, I'll throw in the towel. There isn't anything worse I can think of than not trying to mend things because I'm afraid of the results."