SAM (Agitated) You know, I don’t get it. What do you care if I hook up?
DEAN (Calmly) Cause then maybe you wouldn’t be so cranky all the time.
SAM stares at him, then huffs out a breath and looks away.
DEAN (Sitting up on the bed) You know, seriously Sam, this isn’t about just hooking up, okay? I mean, I, I think that this Sarah girl could be good for you.
SAM sighs and scratches his head. DEAN watches closely.
DEAN (Softly) And… I don’t mean any disrespect but I’m sure this is about Jessica, right? Now I don’t know what it’s like to lose somebody like that…. but… I would think that she would want you to be happy.
SAM is quiet and listening now, tears in his eyes.
DEAN God forbid have fun once in a while. Wouldn’t she?
I’ve talked a lot at random intervals and never as the main subject about how Dean lives a lot in the moment, maybe to the detriment of his future when it comes to stuff like relationships and stuff. I was thinking about this a lot to do with 8x14 - Dean is the one who sees himself dying soon and bloody and doesn’t care about doing the trials if it kills him, while Sam is the one who is uncomfortable settling into the Bunker, with the implication he sees it all as work and has an endgame idea of what a ~real~ home and family could look like instead of a weird underground Bunker shared with your brother. Dean has no problem nesting because he’s making himself a comfy personal space to enjoy right now immediately and to take advantage of everything (like in 8x13 Sam is researching, Dean’s enjoying the showers and dead guy robes etc the Bunker has to offer). Anyway, it reflects in all their thinking about life and the future, to me.
This is another example of Dean’s philosophy and I think it’s something we run into a lot through the years where people are upset that Dean doesn’t seem to be worried or holding out for Cas when he hooks up to cheer himself up or even when he thinks Cas is dead or in trouble. Kinda making this point in part because season 13 may or may not go around upsetting people depending on how Dean reacts to Cas’s death; if it looks permanent to him, he may end up going for cheer up hook ups. He was trying to hook up in 7x04, just 2 episodes after he saw Cas die for good, back then, for example.
I always think this is a very interesting Dean episode, because it’s overtly about Sam, and caricatures Dean in the background to a lot of surface level Dean traits. But there are tells that Dean might be PRESENTED this way but he’s still his usual smart cookie self underneath the partying and obsession with sex and so on - for one thing I’m not even sure Sam realises that Dean never lost his wallet in the first place and was always trying to get Sam back to the auction house, where they’d have hung out fruitlessly looking for it until Sarah showed back up. And when Dean opens up to Sam, he’s very emotionally attuned to how Sam is feeling, and ready with this advice… I know this episode does make him look kinda silly and incompetent at times but it’s literally one of the closest things we have to a rom com episode on this show, and Dean’s playing the supportive yet benevolently manipulative side character to do everything in his power to get Sam and Sarah together, and I think the whole thing sort of frames him that way, starting with the first bar scene where he’s striking out on getting Sam laid - though it looks insensitive to Sam’s eyes and we see Dean through Sam’s eyes not focusing on the case and wanting to kick back, the episode does tell us if we stop looking through Sam’s eyes that Dean is exactly as he ever is…
Anyway just thought I’d add that last comment because I know this episode has a reputation for not being a great Dean episode but I really like it, and I think this comment he has about hook ups isn’t just a flippant thing, but quite meaningful and relevant to a great deal of his characterisation through the show, not just relating to sex but any sort of comfort.