I know right? It's like the more they try to "bond" the worse things between them get haha.
You can thank the long windedness of the series for that. Maybe the showrunners feel that if the Winchesters were too on point they would solve all of the lingering plot threads.
I feel like Dean has a better relationship with everyone besides his brother. I mean, they're functional but there's no love there.
I have a friend who developed the phrase "God dammit Sam" from marathonning the first seven seasons back to back.