I really hoped Sam’s reason for hating Halloween would be more profound, but that’s my only quibble with the whole thing, really.
Like, part of what I really like about the serial killers vs. horror movies Sam/Dean divide is what it says about the two of them, Dean hiding in make believe, stories, because there’s something controllable to them and whimsical and distracting from reality, and Sam whose reality has always been monsters, and therefore finds human monsters whimsical because there’s nothing supernatural about them, and he wishes his life could be that simple.
I love meta diving on all of that, so it’s sad to get such an in depth exploration of Dean’s coping mechanisms with trauma and then get pawned off with an unguessable story about teenage humiliation (although I will admit that there’s something disarming and cute about that too, and not everything has to be exploring emotional depths of our characters, so I’ll still take it as a win.)
That’s partly why I was really happy Sam’s reason for hating Halloween was so… mundane. He really wanted to fit in with these kids, especially this girl he had a crush on. He was probably already hunting by sixth grade (age 12 or so), or just on the cusp of hunting more, and actually being trained to hunt. He’s probably faced down at least one real monster, and been assured by Dean and John that he’s just as badass a hunter as they are. But he wasn’t sure he wanted to be that badass hunter, rather than just another kid who fit in and had crushes and bobbed for apples at Halloween parties, where the only monsters were his friends in rubber masks.
So there he is, sixth grade Sam, living in Bismarck, North Dakota, trying to be Normal Kid Who Is Definitely 100% Normal, fitting in. And he literally… blows it. From nerves, trying to play Normal. For 11-12-year-old Sam, EVERYTHING was riding on his ability to Remain Cool, and he blew it.
And for an 11-year-old, who was probably only a few months past rejecting his Imaginary Friend Sully and deciding he was gonna go be a hunter, who was probably having Major Stress over that loss, and his too-grown-up-for-him choice to hunt, and having what he must’ve thought at the time was one last chance at Normalcy, he associated Halloween as that turning point, that literal change of seasons for him, where he probably thought he would never be normal, never be able to just have friends and go to parties and be a kid again…
I’m sure Jessica’s death two days after his last “normal” Halloween didn’t help matters, but that was not just an embarrassing incident for Sam when he was a kid. And in context with the comparison between Dean’s escapist hobbies delving into Fake Monsters, and Sam’s delving into Human Monsters, it’s an interesting glimpse at what makes Sam tick…