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Sam Winchester was popular and had a lot of friends as he was very involved in school affairs and as well as being a student council member. In short, Sam tries very hard to make a good impression on future prospects and colleges (Stanford, specifically). Sam is literally the embodiment of your typical television high school experience: straight A's, good at sports (soccer, swimming, martial arts, you name it), has a beautiful girlfriend named Jessica Moore and a cool big brother according to Dean himself, and is expected to graduate as... Salutatorian. Despite Sam's best effort to come out on top, there are just some people who were born with the upper hand in terms of intelligence, in which Sam has to compensate for by working extra hard.

Castiel Novak on the other hand is not unknown and a total recluse, and it's probably because of his older brother named Gabriel and thanks to his loyal group of friends he's had since 7th grade. Gabriel is in college now, and because of his astounding popularity and for pulling the best senior prank in the history of his school, people assumed that his little brother might have the same personality. They do not. Castiel has been in school for a while now so why would they randomly assume that now that they're literally set to graduate. Castiel is smart, like crazy smart, in which a lot of people speculated that he traded his sense of humor and knowledge about pop culture references for his photographic memory and high intelligence. Castiel didn't have to try hard in school, always got the highest exam scores with minimal effort, and he was good at martial arts and self defense as well, so despite being your textbook definition of "nerd", bullying has never really been an issue, or at least it hasn't gone far enough for it to become an issue.
Despite Sam and Castiel's similarities, the two have barely interacted with each other in all of the years. Only your occasional being in the same group for a project which was already a rare phenomenon to begin with and it also never helped that Castiel's people skills are also very rusty. So from Sam's perspective, he grew very curious about the boy who literally thwarted his plans to be the batch valedictorian, but whatever, he could still get a full ride scholarship to Stanford to study pre-law through the efforts he's made all throughout high school. Sam tried to befriend Castiel during their senior year, but it's proven difficult to get anything other than a few sentences from that blue eyed boy, which surprised Sam because he thought that they'd be able to bond with their shared wits and... apparently nothing else, oh yeah, and martial arts as well. But like, how do you bond with someone like that with martial arts, huh? To put it simply, Sam tried very hard to break that impenetrable wall of defense that Castiel had when it comes to making friends. It also can't be helped that Castiel's group is literally filled with people who will make you ask why they're friends to begin with. Balthazar and Meg Masters, like seriously? He can understand that he's friends with Charlie Bradbury (the computer geek), and Kevin Tran, who was a junior. He found himself asking what criteria Castiel has in making friends that even Sam's student council charm doesn't seem to work on him. Wait, why is he even trying to be friends with this eccentric shorter man to begin with? It was only a few months before graduation and everybody would go their separate ways, so it probably wouldn't even matter. Sam stopped trying after that.
Graduation day came and went which was weird because Castiel wasn't in attendance. So Sam had to be the one to carry the responsibility of giving a speech to the batch, which was no problem for him, but like, what happened? After the ceremony concluded, he was pulled aside into the office and Sam received the best news he could possibly get, apparently since Castiel had actively decided to decline the valedictorian scholarship for some reason, Sam would receive it instead, which was great because they weren't rich, and even though he had a scholarship, there are still a lot of expenses for dorm, food, and others supplies which weren't cheap.
