AN: Number of times I banged my head against the wall while writing this chapter: 43 So I do apologize for taking such an unprecedented amount of time with it, it was truly a monster to write. I hope someone is still reading this story. I worry that not enough happens in this chapter, which is because this one and the next one were originally intended to be one, so any feedback is of course appreciated. If you're actually reading this, thank you. Enjoy the chapter, and I promise it should start picking up soon!


The lack of a seating chart in biology was both a blessing and a curse. On the plus side, it meant Dean wasn't chained to unsavory neighbors, but it also made the class a minefield. Each day Dean had to estimate the farthest possible point from both Alastair—a back row dweller—and the perpetually contagious Mr. Rutto. So far Alastair had done nothing more than shoot some impressive death glares in his direction, but Dean wasn't going to test his luck by getting any closer to the guy than necessary. He was always relieved when the bell rang to signal his release from that hellhole.

Yet when Dean got to art that morning he suddenly wished he was back in the Advanced Biology warzone. The period started normally enough, Dean fetched his paper and pencil—and now a smile from Anna Milton—and prepared to sketch his baby again. But today Chuck beckoned Dean to his desk.

He reluctantly obeyed, only to wish he hadn't. Laid out on the Formica surface were all of Dean's drawings—three in total—from the first few weeks of school. Chuck was gazing at them thoughtfully.

"I'm very impressed with your work so far, Dean," Chuck began pensively. "You have an intuitive knack for perspective and proportion." The teacher smiled apologetically. "But how many cars do you expect to turn in this year? I'm getting a little tired of 1967 Chevrolet Impalas, beautiful though they may be." Chuck inserted a nervous giggle, and patted Dean on the shoulder. Dean tried in vain to shrink away from the touch. "How about you try something with a pulse this time?" he suggested.

Chuck gathered Dean's drawings into a single stack, indicating as he did so that Dean—who was mortified—could return to his seat. Dean shuffled back, hoping no one was paying attention. But Chuck wasn't done.

The art teacher searched his desk for a stub of chalk, and having finally produced one write in large, squeaky letters on the blackboard: Portraits.

"I've noticed many of you have a favorite subject," Chuck began, using the teacher voice, and thank god he didn't look directly at Dean. "But the point of art is variety. It's important that the artist captures the essence of life, of humanity. For that reason, I am asking each of you to draw a portrait."

Around the room, the whispers of indignation began. Chuck was giving an actual assignment? Was he high? Had he run out of booze? Who the hell did he think he was, leaving them to their own devices and then making demands? Who died and made him king? One boy demanded. It's like he thinks he's god, a girl countered.

"Now, all of you calm down," Chuck's voice boomed over the frantic exchange. "Your portrait can be of anyone—though I'd prefer it not be yourself—and I don't care what medium you use. If you really want to, you can even sculpt it."

That seemed to pacify the group a bit.

Dean, on the other hand, was in no way comforted by the lack of restrictions. He had to draw a person. He'd have to get a photograph, and he'd probably have to explain why, and that meant alerting another human being to the fact that he took art.

Anna noticed his demeanor and sent him a grin from across the table.

"This assignment sucks," she complained. The look on his face agreed with her.

"I thought you liked drawing natural stuff," Dean grumbled.

"Yeah, trees, landscapes. It's not drawing people that's so bad, though. I just hate being told what to do," said Anna.

"I know that feeling," Dean muttered in response.

Anna smiled to herself. She could see why Castiel seemed to like Dean Winchester. She hadn't been too pleased about the move—it wasn't her fault Lucifer was dumb enough to get caught—but things were starting to look up. Anna wanted to be able to consider Dean Winchester a friend. She knew Castiel did, and she wondered if Dean returned the sentiment. Dean wasn't the kind of person she would have expected Castiel to be friends with, but her brother's friends were never what she expected.


"There is a lot of guilt in this novel," Ms. Rosen was explaining. "Guilt over the broken friendship, obviously. But many readers believe that there is also another guilt, a guilt these two boys are afraid to even admit. In the setting of this book, they could have been arrested for confessing that they have repressed sexual feelings for each other."

While Dean and Anna were bonding over a dislike of Chuck Shurely's new 'I actually give a crap about what you guys do in my class' policy, Sam Winchester was taking notes on textual clues in A Separate Peace. According to his teacher, everything in the book was symbolism for Phineas and Gene's repressed feelings for each other. Sam didn't take much stock in it, because as far as he could tell, Ms. Rosen felt every literary character was secretly gay.

He glanced towards to front and to his left, to where he knew Jessica Moore's assigned seat was located. Sam sort of missed hanging out with her. Jessica had never been anything but nice to him, but she was Brady's friend, not his. Brady. It still hurt to think about how Brady had treated him. Sam wished he was the kind of kid who skipped class so he wouldn't have to look at Brady's stupid smug face all through biology. Sam stared at the clock and wished he could just go straight to math. Algebra was easy enough that he didn't need to pay attention, which meant he could spend the whole class talking to Ruby. He was really beginning to like her. She was a year older, a sophomore, but she didn't talk down to him or act like she was better than a mere freshman like Sam Winchester. And she was honest. Ruby and Dean had lunch together and she'd confessed to Sam from the beginning that the two of them were not friendly. She'd also promised to try to get along with him for Sam's sake, and that meant a lot. Sam hoped Dean would be equally willing.


Dean entered the cafeteria after the bell carrying his paper bag of lunch. He noticed Ruby sitting at a crowded table and realized she must have found some friends in their lunch period. Good. Dean ducked past the group, hoping she wouldn't see him and try to talk to him. He chose an abandoned corner table near enough to hers to keep a close eye on the girl. Dean wasn't comfortable with Ruby's friendship with Sam. Preoccupied as he was with observing Ruby, Dean didn't notice the figure quietly approaching his table. He didn't realize another person was present until the newcomer spoke.

"Hello, Dean."

Dean startled, spinning his head in the direction of the sound.

"I don't suppose you'd mind if I sat here?"

Castiel Milton was standing in front of his lunch table.

"Of course not, Cas, happy to have you," Dean said quickly, not even realizing that he'd shortened Castiel's name until the words had already rushed out of his mouth. His hands, halfway to his mouth with an unsatisfying peanut butter sandwich, stopped suddenly as, for a moment, his entire body froze. Castiel reacted similarly, and their eyes met, Dean's asking silently for permission, Castiel's giving unspoken approval. And then everything returned to normal; Dean bit into his sandwich, Castiel sat down.

At first the table was silent; nobody knew quite what to say. Cas realized that he barely knew Dean Winchester. He knew that his mother was dead and his father mostly absent, that he had a brother named Sam who was a freshman and who he loved fiercely, he knew that Dean took music and art and that he hated Mr. Guerre's lectures and that he thought Paradise Lost was dumb, and he knew that Dean liked to shorten names.

Actually, he didn't really know that. He was just working off the example of his own name. Castiel had never had a nickname. Anna had tried shortening his name on occasion, but it was awkward to do in the Milton household. Gabriel had no shortage of nicknames for everyone, invariably dirty or insulting or whatever passed for witty under when viewed through Gabriel's twisted sense of humor. Michael always called him Castiel, so he was Castiel. He had never been Cas. He liked the way Dean had said it, how it had just slipped out like it was the most natural thing in the world.

"Okay," Dean said, snapping Cas out of his reverie, "time for a game of twenty questions."

"What?" Dean wondered if Castiel knew that he tilted his head when he was confused.

"You know, one of those stupid 'get-to-know-each-other' things they make you do? Take turns asking dumb stuff like your flavor of ice cream?'" Castiel's eyes showed no sign of recognition. "There's just two main rules: no answering a question with another question, and you have to answer honestly." Castiel still looked hopelessly lost. "Alright, I'll go first. I'm sure you'll figure it out."

Dean paused to think of a question. He didn't want to waste it—he had to admit that Castiel was intriguing as hell—but he didn't want to start with anything too personal. It was one of Dean Winchester's golden rules, no chick-flick moments.

"How many brothers do you have?"

"Four. And two sisters."

So there was another Milton brother Dean hadn't met. That put him at three out of seven.

"Alright," he said, "your turn."

"What?" Castiel asked again, obviously still not understanding the game. He was the first person Dean had met who had never heard of twenty questions, and it only served to boost Dean's curiosity.

"Ask me a question," he explained.

"What about?" Castiel answered, and Dean wondered if it was even possible to be this clueless.

"Anything. Something about myself. Like what I asked you, about your family."

"Oh," Cas frowned. "Okay, um… how many brothers do you have?" Unoriginal, but Dean took pity on Castiel and decided to go with it. At least the poor guy was trying.

"Just Sammy. No sisters, either, just the two of us. And our dad, when he chooses to show up."

Dean tried to think of a good question.

"What's your favorite color?"

It sounded stupid and babyish, but it was the best he could come up with.

"Green," Castiel replied immediately. He had no idea where that answer had come from. Castiel had never given much thought to which color was his favorite. Cas didn't realize it, but the reason green was the first color to come to mind was that at that his eyes were awash in green. His eyes were staring into Dean's.

"Uh…" Now that the topic had been broached, Cas realized that he was dying to know Dean's favorite color, but he couldn't steal Dean's question twice in a row. Quickly, Castiel tried to think of the kind of question Anna would ask, or Rachel. His sisters were so much better at this than he was. "What's your favorite band?"

Dean chewed his sandwich pensively. This was a question that he would have to give some thought.

"That's tough, man, real tough. I like all the classics. ACDC, Led Zeppelin, Bon Jovi. Kansas."

"I actually have no idea what any of that music sounds like," Castiel confessed.

Dean's eyebrows shot up. Castiel Milton was one weird kid.

"Dude, someone seriously neglected your education. Guess it's up to me to teach you some culture. Okay, um… how many books have you read?"

"I've lost count. It's somewhere in the low hundreds."

Dean shook his head. And he thought Sam was a nerd.

"What's your favorite subject in school?"

Cas knew, especially combined with his last answer, that question made him look like a nerd. He felt his face heat up and hoped it wasn't turning red. When girls blushed, it was endearing. When boys blushed, it was pathetic. Michael had told him that.

Dean didn't know how to answer Castiel's question. One thing immediately sprang to mind, but there was no way he was going to say that. Then again, he was supposed to be answering honestly. He could tell from the look on Castiel's face—was he blushing?—that it had never even occurred to him to lie, and Dean couldn't deal with the guilt of lying to someone like that.

"Uh, art, I guess," he said, hurrying to qualify it with, "I mean, Chuck is pretty cool, he doesn't make us do anything dumb, you know? What's yours?"

He'd let Castiel steal his question for free earlier, so Dean figured he'd earned the right to use the same technique to change the subject. Castiel didn't even seem to notice.

"Oh, I suppose mine is art as well. At my old school it was history, but Mr. Guerre's class leaves… something to be desired."

Dean chuckled.

"Guy like you, gotta say I was expecting English."

Castiel shook his head slowly.

"English classes make you read old, famous, books, many of which do not live up to their reputations. And when they do teach about truly great books, they are full of lies and their own ideas of what they have to mean and they ruin them. I'd rather read classics without all the strings attached."

"Huh."

Dean took another bite of his sandwich. He thought it was kind of weird that Cas wasn't eating, but he could have had something before he sat down. Dean didn't spend any more time on it.

Across the table, Cas watched Dean eat. Cas didn't like eating lunch, but he often found the choices of others provided great windows into their lives. It was embarrassing to admit, because he knew it was rude, but Castiel loved people watching. And if his specimen just happened to be someone especially interesting, like Dean Winchester, Cas couldn't help but be captivated.

The question he hadn't asked earlier was on the tip of his tongue, about to spill out, and Cas was growing nervous. It was his turn and he was taking too long. He'd managed to distract Dean for a minute with his speech about the sins of literature in education, but he needed a question now and he wasn't ready. Dean had turned his own question back on him, though, so didn't that mean it was okay?

"What's your favorite color?" Cas blurted out, unable to resist any longer. Dean was looking at him like it was the most mundane question in the world, and suddenly Cas was embarrassed that he had exclaimed it like it was something important. And yet to him it was of great import. He wanted to know.

"That's your question? What's my favorite color?" Dean asked, masking his amusement with faux skepticism.

"Yes," Castiel snapped, ready to defend himself.

Dean shrugged and went back to concentrating on his sandwich.

"Blue," he said.


Dean and Cas walked to history together. They sat down at their adjacent desks and complained about the lecture topic being the Reign of Terror for the third day in a row. There was a rumor running through the school that Mr. Guerre and Mr. Rutto were locked in a fierce competition to see who could put more students into comas just by talking. Dean knew he was biased because he was also too edgy in biology to fall asleep, but after today he was starting to give the edge to Guerre. He glanced at Cas, who was occasionally scribbling in an open notebook. It figured that Castiel Milton would be the kind of diligent kid who took notes in class even though he already knew everything. Dean tried to read what he was writing but he was at the wrong angle to decipher Castiel's tiny, looping script.

Halfway through the class the notebook landed on Dean's desk, startling him out of trance. What Dean had assumed was a page of notes on the Reign of Terror was, in fact, a neat column of tallies labeled 'Number of Times Mr. Guerre Has Uttered the Word 'Guillotine' Today' with a note saying "Did I miss any?"

Dean grinned involuntarily. He'd found himself doing that a lot lately, more than he could remember doing in a long time. For the last few years most of his smiles had been forced, mainly for Sam's benefit.

"I was zoned out," he scrawled back, "but I think you got them all."

He did a quick count—there were twenty-five tally marks—before passing the notebook to a grinning Cas. So much for the obedient little student. This, Dean realized, was what it felt like to have friends.