Dean gets it and he's not asking for an answer right now about what Sam is going to do. He expects Sam will have to do some research and some discussion. When Sam changes the subject, he's happy enough to talk about other things like what Jo is up to and what's been going on at the bar and the garage.

Castiel is a good choice. He understands human life and love. He understands how mistakes can be made. For Dean's part, he keeps an eye on Sam, asking regularly if he's doing okay, and giving him odd jobs as a distraction. It doesn't matter so much here if Sam gives someone the wrong drink; he can always make another right drink. But it's noticeable to most people who see Sam regularly that something is up.

Time in Heaven works differently anyhow. It's a good thing Sam takes some time to consider it because that's the first thing that Dean is going to ask him. Dean hears Sam come in the garage and hollars out 'Hey, Sammy," from underneath the Impala. He slides out on the mechanic cart and sits up, reaching for a rag to wipe his hands on. Dean leads him over to a small area furnished with a couple of bench car seats and a rough, wooden table. He sets the plate on the table and goes to the mini fridge to pull out a couple of beers then sits opposite Sam, passing one beer to him. "You've got your something face on. What's up?"