Dean's summer rocks, all the way up until Friday night. He spends it mostly with Anna, who he honestly can't thank Cas enough for introducing him to. She's beautiful, smart, and a firecracker in the bedroom (or the back of the Impala, as the case often is). Sam is a little shit who constantly cracks jokes about What in the world does she see in you, Dean?, and while Dean knows his little brother is only giving him a hard time, it cuts deeper than he'd like to admit. Anna Milton is perfection in a pale-skinned, redheaded package, and he knows she probably wouldn't have ever given him the time of day if not for Castiel talking him up. Dean doesn't know how he got lucky enough to have the perfect Anna Milton as a girlfriend and the perfect Castiel Shurley as a best friend. Don't get him wrong, he loves Charlie, but they're both pretty low on the totem pole of high school (and life).

Dean and Charlie are Grade-A nerds, and they fly that flag pretty proudly. Charlie, at least, has a leg up on Dean in that she's incredibly smart, to boot, but she's also happens to be gay. Dean doesn't mind it one lick. Charlie is awesome, and the two of them often find themselves commiserating over relationship woes and porn. High school and a small town, however, aren't quite as kind to Charlie. She never seems to mind though. Dean kind of admires her for that, wishing he had half the guts and confidence she does. But it remains that they fall pretty low on that totem pole.

Castiel and Anna, though? They're fucking paragons of the community. Cas likes to claim he's nothing of the sort, but Dean is quick to disagree. The only things that bring Cas down is that he insists on continuing to hang around Dean and Charlie (which Dean will never not count his lucky stars for) and that he stopped going to church a few years back (which Dean doesn't think impacts that much, but Cas claims different). Otherwise? Castiel Shurley is every bit as out of his league as Anna Milton. They're both so fucking smart it hurts, neither of them in a single one of the basic classes with Dean. Nope. They're full-blown honors and AP class, Ivy League school bound geniuses. Dean isn't bothered by that though, since he knows they both work their asses off for it. Dean has sat around enough summers with Cas while he studies (and then done the same with Anna this summer) to know it.

On top of the brains, they're both Grade-A hotties in their own right, and could have their pick of anyone in the school. Oddly, the both of them seldom date. Anna told Dean early on that he was only like her second boyfriend or something (though whoever her last boyfriend had been must have taught her a lot because hot damn), and Dean is certain that he's never seen Cas have an interest in anyone (though he's seen plenty of pretty girls bat their eyelashes at the oblivious guy, and Dean swears he isn't jealous of the attention).

And then there's the fact that both of them know basically everyone in the town due to the community church. They're the apple of the whole town's eye, neither one of them ever once getting into an ounce of trouble. They're gorgeous, well-liked, straight-A students that every parent in Lawrence tells their kids to look up and aspire to.

So yeah, Cas and Anna are perfection on legs, bound for so much more than their small town of Lawrence, and Dean is glad for every day they don't seem to realize they're too good for him.

But the last Friday before senior year, Lisa Braeden throws a giant house party. Normally, Dean would be all for a chance to get three-sheets-to-the-wind wasted before he has to start back to homework and tests, but this year is a little different. He knows before he even asks that Anna won't go. Anna Milton does not go to parties, and that's one large difference between her and Cas. Cas will at least attend and act like a somewhat normal high school student, but Anna swears that the "underage fraternization" is what separates those that get accepted to Brown from those that go to KU.

He asks all the same, but, of course, she says no (It's the weekend before school, Dean, I have to make sure I get prepared). He almost doesn't go himself, but Charlie talks him into it, saying things like come on, it's senior year! and we've barely hung out all summer, so he goes.

When he gets there, the party is already in full swing, so it takes him a moment to stake out Charlie and Dorothy, and he's pleasantly surprised to find Cas there as well. He was a little worried the guy was going to pull the same thing as Anna and stay in because school is starting in two more days.

He realizes as he comes up to them that it really has been awhile since they all hung out, and says as much himself. "Hey guys, long time no see, how's it going?"

Dorothy responds, "We're at a party, genius, how do you think?" Her delivery is a little snippy, but Dean doesn't think anything of it; that's just how Dorothy is. There was a time they didn't get along at all, her calling Dean a neanderthal, and him calling her stuck up, but once they both realized they were stuck with each other via Charlie, they figured out how to get along. That doesn't mean they don't still give each other a hard time though.

And he figures she's right about the party- of course it's going well. There's booze and loud music- Lisa's parties are the stuff of high school legend. He's always had a good time at Lisa's (and sometimes with Lisa, though that won't be happening now), and he's prepared to do that tonight until Charlie reminds him of why he almost didn't come, asking, "Where's Anna?"

It's a like a punch to the gut, but he tries to shrug it off, act like it doesn't bother him one bit that his girlfriend would rather be out studying than out with him on the last weekend before school. But he supposes he did hoard a lot of her time this summer, so he can't be too upset. "You know Anna."

Charlie shoots him a sympathetic look. "Won't even come to a party for you?"

She really isn't helping him feel any better, but he shrugs again. "I mean, it's not a big deal. Everyone knows Anna doesn't party, and we spent enough time together this summer. She deserves some time to do her thing, you know?"

Charlie and Dorothy both nod before Dorothy asks, "So did you get the summer reading done?"

"Are we seriously talking about homework at a party?" Charlie whines.

"Yes, because unlike some people," Dorothy emphasizes the statement with a hard look at her girlfriend, "some of us actually have to make an effort."

Charlie pulls a face. "I make an effort."

Dorothy rolls her eyes. "Yeah, in breaking into the school records to change your grades."

"Exactly!" Charlie chirps with a bounce and a flick of her hair. "I earned those grades through hard work. Maybe just not the kind of hard work the teachers intended."

Dean can't help laughing at the couple because damn. They really are a blast to be around.

Dorothy finally stops shaking her head at Charlie and turns her attention back to Dean. "So, the reading, you do it?"

"Yeah," he responds, sticking his tongue out. "Anna made sure of it."

Charlie laughs good-naturedly. "Man, you're so whipped."

Dean just flips her the bird, grinning at her the whole while. "Like you're not."

She laughs with a, "Screw you, Winchester."

He just grins wider, and then turns his attention to Cas. "What about you, Cas? Anna said you guys had some rough stuff this year."

But Cas doesn't answer. He's glowering at his beer bottle instead. As a matter of fact, he's been suspiciously quiet the whole night, didn't even say hey when Dean walked up. It kind of pisses Dean off, actually, because the alternative is to feel bad, and he already has enough insecurity where Cas and Anna are concerned that he doesn't want to dwell on that tonight.

"Dude, what's wrong with you?" he finally asks. The last thing he expects is the vicious glare Cas sets on him, so harsh it knocks the breath out of Dean. They stare at each other for what feels like hours, awkward silence crackling between them, completely oblivious to the party raging around them.

Finally, Cas looks away, grumbling, "I need some fresh air," before stalking off.

He can't help feeling hurt, but the Dean Winchester way of dealing with feelings is to get angry. "What the fuck is his problem?"

Charlie rounds on him, expression like a thunder cloud over water. "Seriously, Winchester!?"

He backs down a bit in the face of a pissed off Bradbury (because damn if Charlie didn't get her mother's temper). "What!?" Because really? What the hell is going on here?

"You ignored him like all summer! His feelings are hurt!"

"I did not!"

"Really? Then when was the last time you saw him?" Charlie puts her hands on her hips in an expression of go on, prove me wrong, I dare you.

And he hates to admit it, but when he actually thinks about it, he realizes he actually hasn't seen Cas since school ended. He glances at Dorothy who is no help at all because she just shrugs at him, giving him the you-done-fucked-up-Winchester look.

She nods her head at his silence. "And how many times did you blow him off for Anna?"

That one bothers him. "He said he understood!"

Charlie rolls her eyes so hard he's momentarily concerned they're going to get stuck in the back of her head. "Of course he said he understood! It's Cas! He isn't going to tell you he's upset over something like that."

"Well why the hell not!?"

Charlie lets out the most exasperated noise. "Seriously! Do you even know him!? He set you and Anna up! He isn't going to come between you guys! God! Some best friends you are!"

That one goes straight through his heart because she's right. They've been best friends since they were four, but yet he somehow missed this. He refuses to take all the blame, though, because after fourteen fucking years Cas should have learned how to fucking tell Dean he was mad at him!

Dean doesn't stay much longer, suddenly altogether not in the partying mood. He was managing without Anna by his side, but now with Cas pissed at him, he isn't managing anything. Without evening having one beer, he climbs back into his car and heads straight home, curling up in his bed (thankfully, no one is still awake to question what he's doing home so early). He contemplates texting Anna, but decides against it. She's probably busy doing her brainiac thing, and Dean doesn't want to get in the way of that. It's a pounding reminder that he isn't good enough for two of the people he cares most about.

He spends the whole night tossing and turning, his brain refusing to shut off. At some point around five, sleep drunk and delirious, he texts Cas an apology. He agonizes over it, not wanting to come off too clingy, but wanting Cas to know that he knows he screwed up. He finally settles on sry man. charlie n i talked last night n she told me what an ass i was all summer. can u forgive me?

He goes down for breakfast not too long after. When he still hasn't heard from Cas after eating, he sends Anna a text saying "wat u up to 2day babe?"

Anna doesn't respond either.

It's about ten in the morning when he finally hears back from Cas, "it's ok. i understand. we'll talk later. not feeling well today." He feels guilty somehow, unsure if Cas really does feel bad or if he's avoiding him. He wants to ask Cas if he should come over, but something stops him. He doesn't want to bother Cas if he doesn't want to see him, so instead he responds, "thats cool. hope u feel better. call me whn u do?" He feels a little better when Cas says he will.

It's about another two hours later when Anna texts him back saying, "not feeling well. Gonna stay in bed. sry."

Dean sends back "hope u feel better soon. dont want you to miss the frst day of school".

Anna sends back "lol god no".

So Dean goes and pesters Sam until the kid agrees to have a Star Wars marathon with him to distract him from his loneliness (but of course he doesn't tell Sammy that's why, instead opting to act like he's doing the kid a favor).

This is going to be how this story is told- alternating POVs of the same events. I recently read Dean Winchester is a Gay Virgin by bettydays (which, btw, if you haven't yet read, you should, as well as everything else she's ever written; you can find her over on AO3), which also uses the tactic. I fell in love with the idea and realized it was the perfect way I wanted to tell this story. Despite the overlap in content, though, I'm hoping it doesn't get too repetitive.

Also, huge thanks to pharocomics, without whom, this was basically illegible.