Okay, I try SO hard to watch the Dean and Aaron scenes from a het POV and I just…I just CAN’T (accidentally long post incoming, sorry not sorry)

Sure, it’s possible he was disappointed because it was just a chip to his ego that Aaron wasn’t actually into him. Though it shouldn’t be THAT much of a chip if he’s such a confidently straight “lover of the ladies” but that’s besides the point.

Honestly though I think he was more disappointed at himself! Because Aaron’s con WORKED! A guy hit on him, visibly flustered him and successfully threw off any suspicioun! The Winchesters pride themselves on being composed and collected during hunts: it’s hard for their enemies to faze them unless they dig deep. They also tend to be good judges of character, especially on investigations. Dean’s initial instinct was right after all: Aaron was tailing him.

It’s never good when someone is able to slip past their radar. So the fact that it happened because some guy simply flirted his way past him and got away with it? How EMBARRASSING for him!!

This is something that would never happen to Sam, even if Sam is into men too. When Balthazar calls Castiel Sam’s boyfriend, Sam runs with the joke and takes it in stride. When Balthazar says Cas is in love with Dean he just sort of 404s out. Sam would be flattered by Aaron, amused maybe, but otherwise unbothered by it. I honestly think he would’ve been smart enough to see past the flirty ruse. But Dean is just THAT much of a disaster when it comes to men that one forward guy is enough to throw him off his game!

It’s the same as the Siren. He takes that situation hard not because his Siren was a dude, but because he fell for it! He and Sam thought they’d be able to spot the siren a mile away (he even gave Sam a hard time when he thought the girl was the siren) but the Siren took him completely by surprise! He made him feel comfortable and safe! He let down his defenses enough to share a drink with him!

While you could argue that the Siren tricked him on a platonic level by presenting himself as the coolest guy / best bro ever, Aaron didn’t trick him with friendship. It was a straight up, no-other-way-to-interpret-it proposition asking him out.

And the fact that Ben Edlund and Phil Sgriccia discussed Jackles’ acting choices and agreed that he added some romantic fluster to his response in the situation?? INSANITY.

Anyways, it really goes well with the theories that John Winchester might not have been openly homophobic but would’ve adopted a military-like “don’t ask, don’t tell” mindset because he would have seen Dean’s queerness as just another a weakness the enemies could use against him. The same reason why they are afraid to have close relationships, to show any emotion or vulnerabilities, etc.

It’s no wonder so many bad guys use his obvious connection with Castiel against him. My favorite instance of this is when an angel is able to break his grip and escape at the mere mention of Cas.

Anyways, kudos to Aaron Bass (a HUMAN no less!!) for spotting the world’s most repressed bisexual and effectively utilizing that to his advantage. You have to respect it.