It's very plausible that Sam needs Dean to see it to be able to challenge himself to wallow less and come up with ideas even if he doesn't know how yet.

Sam pauses long enough to nod at that. His mistake doesn't change how proud he is of Jack for fixing for souls that didn't deserve to be trapped in a hunger games wasteland to punish them.

He decides to finally have some of his beer with Dean hitting in on the nose without realizing it. He's not frustrated with anyone other than himself though. He lets the liquid poison sit on his tongue for a moment to think of how to answer Dean, the taste reminding him of the worst hooch he's had in his life, before swallowing it down like cough medicine. "No...No. In fact she wanted to know where she was and she thought that this all was too good to be true until I sat her down and talked with her." Which is besides the point. He rolls his shoulder uncomfortably, eyes looking up as if to search his mind that his tongue can't quite push out on its own. "We got...to talking about what she remembers from the last time I saw her and focused on that so she could hold on to something. I...landed in bed with her."