From this picture, we would assume that Dean passed out in the middle of a particularly kinky fling.
How did he get back? Did he and the woman have this soft-bondage fling in the room, without waking Sam up? Did Dean walk home from her place, fully dressed, bra and tie and flog around his head, only to pass out mere feet from the bed?
The last time we saw Dean hungover was “Beyond the Mat,” where he had to get drunk for case purposes and Sam was a total dick to him. In contrast, this time, Dean’s gotten drunk for fun, and Sam gives him a pitying look and lets him sleep in.
And then there’s breakfast.
When Sam gets back from the interview, it’s exactly in time to see Dean, in sunglasses, loading up on bacon. His favorite food, bacon.
Because as Dean knows, nothing treats a hangover better than a big pile of bacon.
Basically?
Dean’s being a massive faker, trying to pretend that everything is fine. He’s weirded out that Sam is mothering him, and so he’s determined to prove that he’s living the same great life as always.
He wasn’t nearly as drunk as he’s pretending to be. The flogger and the bra are plants. The alternative is that a woman decided to leave at least $40 worth of stuff with her random drunken fling.
This is a thing that women generally don’t do, and what’s more, the writers know they don’t do it. Once previously, they used a pile of discarded lingerie and clothing to imply that a massacre, not an orgy, had taken place.
That scene, like this one, requires the viewer to look deeper in order to see a truth that is much darker than what is originally implied.
Sam and Dean can track each other’s phones. Dean knew when Sam would be on his way back, and he timed it so that his brother would have front-row seats to the breakfast scene. Dean went out of his way to play up the contradictory states of 1. craving bacon and 2. being massively hungover from partying.
Dean says “whatever happened to you being nice to me” hoping that he’d worn out Sam’s patience and things would go back to normal. Instead, Sam pulls out a gift bottle of alcohol.
Dean instantly drops the pretense of being hungover. He takes off his glasses, doesn’t protest the volume of Sam’s voice, and starts working the case. He’s also eating his bacon as obnoxiously as possible- not because he’s hungover, but because he’s fucking with Sam.
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