As uncomfortable as it was to talk about, maybe that's what they needed. To get the words out there in the open. 'Hi, my name is Sam Winchester and I'm a demon bloodoholic', 'hello Sam'. They probably already knew how the other felt about a lot of the bad shit that had happened. But saying it out loud? Maybe that's what they needed to move on.
Dude! He wasn't a cushion, damn it! Fine, if he was a cushion, then Dean was a table. He rested his cold, damp with condensation bottle on Dean's shin and leaned over to reach a protein bar, settling that on Dean too. "At least there's one difference between us and Dad... we're not dragging our kids into this life." Maybe because they didn't have any kids, but, y'know, details.
"And we've got something else Dad never had." He turned his head to face Dean, a ghost of a smile curving onto his lips. "We've got each other."