With Dean going home with some chick he picked up at a bar you had all been at, you and Sam decided to head back to the motel with the slight buzz you’d both accumulated throughout the night.

Which, in the end, is what led you both to strip down to your underwear (swimsuits weren’t a Winchester certified necessity, after all) to go swimming in the motel pool because, why the hell not?

And it was just the two of you.