Hook Man tag
Sam doesn't think he can move on from Jessica yet - it's way too soon, as much as he likes Lori. The woman he loved is gone, it's his fault, and it feels wrong to have feelings for somebody else. He gets why Dean is encouraging, this, though - he wants what's best for him and always has. He doesn't fault his brother for it, could never do so.
Sam has absolutely no clue what the future holds but he's looking forward to having a life beyond hunting again. It's what is keeping him going at the moment despite the current shitstorm.