Dean Winchester sits in his usual spot in the back corner of the courtyard, a half empty bottle of Mountain Dew and a sandwich wrapper on the table in front of him. He wipes the crumbs off his hands over the ground, looking around the open space at his peers. The weather had warmed up since the week before, leveling out at a breezy 75 degrees. Dean rolls up the sleeves of his red and black flannel, sitting up when the sun kisses his skin. He sits alone, flashing a charming smile as people pass.

Soon enough, Crowley, Benny and Garth sit around him with their trays of the normal high school mush.

"I've only had one year of this shit they call food, and I'm ready to graduate," Benny grumbles, poking the bread of his chicken sandwich with his pinkie.

Garth rolls his eyes, taking a huge bite from his own sandwich before speaking. "Just 'oll with it 'enny."

Benny grimaces, shaking his head. "I'll go with it when they serve real food."

Ignoring the other two boys, Crowley focuses on Dean, who laughs silently. Crowley was a junior, the other three sophomores. He's in Dean's shop class and quickly latched on to Dean when he found out he was handy with a hammer and some nails. His dark eyes scan the crowd around, then stop. His signature smirk decorates his lips, and he turns to Dean. The other boy raises an eyebrow at Crowley, taking another swig from his Mountain Dew.

"Novak isn't wearing his usual outfit," Crowley says, looking away again.

Dean follows his gaze across the courtyard, searching for the boy's tan trench coat and dress slacks despite the fact Crowley stated he's wearing something different. Not too far away from their table, the boy sits on the brick wall lining the courtyard, legs crossed underneath him. Dean's breath hitches for a second, a small noise no one else at the table heard.

Castiel Novak wears a pair of dark jeans, a black t-shirt and a pair of white Vans. The blue of the jeans is fadedaround the knees and thighs, frayed at the hems, and the shirt hugs the slant of his shoulders to his hips. Dean bites the inside of his cheek. Crowley searches his face, smirks even more when he sees the faint flush to his friend's cheeks.

"I dare you to go over and compliment him," Crowley baits, knowing the infamous Dean Winchester would never let anyone make him look like a coward.

Dean's gaze focuses on Crowley again and he stammers for an answer, for a comeback to get him out of it. But the other boys had heard it and started laughing. Benny smacks Dean's shoulder, holding it for a second as he doubles over.

"Deano giving Novak a compliment?" he wheezes between bursts of laughter. Garth also laughs, nodding in agreement.

Dean glares at his friends, then glances back at Castiel. He doesn't know much about the boy. He's a freshman, is an editor for the paper, is his class's vice president, and gets straight A's. Dean heard from his friend Charlie that Castiel did well in math, but killed in English. And he always looks like a professor from Harvard or something.

In all honestly, Dean had pondered over the slight tingling sensation he gets in his gut when e looks at the guy.

And Dean Winchester never backs down from a dare. If the people call, he answers.

So with a giant inhale, Dean brushes his hands on his own ratty pair of jeans before pulling out his phone. He takes a second to stare at his friends and survey their expressions. Crowley smirks knowingly, Garth smiles as he eats, and Benny raises an eyebrow. He stands slowly, trying to not startle anyone around them into looking at him. He keeps his head down as he approaches the freshman.

Castiel doesn't notice Dean walking towards him until he is a few feet away. The boy looks up from his lunch, tilting his head slightly in question. Dean blushes, pushing aside the thought that the freshman's cute when he does that. He clears his throat and stands up straight.

Dean looks Castiel up and down, smiling, and says, "Damn, Castiel."

Castiel's eyes widen and he looks down at his lap, shaking his head. For the first time, Dean really sees those sharp blue eyes and the mess of curly black hair. For the first time in a while, Dean feels his stomach drop when a blushing Castiel stares up at him with the smallest of smiles.

"Hello to you too, Dean."

Dean steps back, rubbing the back of his neck and smiling awkwardly.

Behind them, Crowley, Benny and Garth laugh.

…

The next day, Dean searches for Castiel in the courtyard as he sits down with his lunch. He doesn't spot the freshman right away, brooding over his lunch as his friends settle around him. They chatter over their own trays, discussing the homecoming dance and how they plan to ask girls out.

Crowley rolls his eyes at Garth and Benny's horrible romantic skills. "Listen boys, you have to woo her. Don't just ask, mean it. Show her you mean it, either in your vocal inflection or which something simple like a flower."

Benny scoffs, pushing around green beans on his plate. "And since when did you become the love expert."

Garth snorts, poking Benny in the shoulder. "Since he got a girlfriend, remember?"

Shaking his head, Benny looks at Dean, who still scans the courtyard.

"You looking for something, brother?"

Dean blinks, finally looking at the boys around him. He smiles quickly to apologize, then opens his sack lunch to grab a bag of chips. "Nope."

Benny raises an eyebrow but doesn't press. The boys go back to discussing proper wooing techniques, Dean now actively paying attention. He still rakes the crowd for a strip of tan, or the flash of blue eyes, something to tell him that Castiel had made it to lunch today. An image of the boy's expression yesterday appears in his mind, and he grins.

When he gets up to throw away his trash, he spots the freshman sitting in a different sunny corner. Dean grins, noticing that the boy has kept his casual look, including the Vans. Dean purposefully walks past him, looking him up and down again. Today, he notices the angle of Castiel's jaw line, the straight slope of his shoulders, the smooth lines of his waist.

"Damn, Castiel. Back at it again with the white Vans."

Castiel's head snaps up, and he unleashes the most genuine, adoring grin on Dean. His eyes shimmer, dimples shaping the smile. Dean's heart skips a beat, his hands sweat, his stomach flips. Without thinking, Dean winks, which makes Castiel laugh. Peals of baritone laughter follow Dean down the hallway.

Dean doesn't want to admit it, but it gives him a little bounce in his step.

…

This goes on for a week. Dean looks Castiel over, taking note of his new outfit. Castiel blushes and smiles. Dean says his catch phrase, occasionally throwing in a wink for good measure. And Dean's friends hound him about it.

Benny wraps his arm around Dean's shoulders. "Dean you've been checking Novak all week, just ask him to the dance already."

Garth walks backward in front of them, nodding his head as he glances behind him. "He'd say yes."

Crowley smirks the entire time, standing tall and silently taking credit for Dean's new crush.

Dean shakes his head, hugging his binder for Calculus to his chest. He watches his feet walk across the linoleum tile, counting each step to tune out his friends comments. He'd been thinking about it all week. One thought plagues him though. Just because he compliments the freshman every day for a week doesn't mean that he'd want to go to the dance with Dean.

"I don't know guys…." He mumbles, still watching his feet.

Crowley elbows him. "Would if help if I dare you to?"

….

At lunch, Garth, Benny and Crowley push Dean away their table. They shoo him like a pigeon, snickering and whispering among themselves.

Dean stands awkwardly in the courtyard, navigating the tables and faces around him. His entire body quivers, muscles twitching as he walks around. When he sits on the brick wall, feet dangling over the edge, they still shake. He clutches his lunch in tight hands to hide the fact they're wobbly as he continues to look for Castiel.

He spots the freshman walking towards him, head tilted and a curious smile on his face. When he's within earshot, Dean says, "Mind if I join you?"

Castiel's eyes brighten, or so it seems to Dean. He reasons it's the sunlight, rubbing the back of his neck as the freshman sits next to him. The other boy wears a black button up, the sleeve rolled to his elbows. His faded blue jeans make the outfit more casual than his previous one. Dean notices a flash of white as the boy positions his legs under him. Castiel opens his water bottle, gazing at Dean and raising an eyebrow.

Dean gulps, rubbing his palms on his jeans. Him, Dean Winchester, womanizer, afraid of asking out a cute boy? No. That's not his way. He's not a Losechester. He's a Winchester. And Winchester's have the guts to put themselves on the line.

"So, Cas… the homecoming dance is this weekend," Dean offers.

Castiel nods, tilting his head at the nickname. He says nothing of it, but still grins about it. "Yes?"

Rubbing the back of his neck, Dean looks away. "Well… I was wondering if you already had a date."

"I do not."

Dean's gaze locks on Castiel again, hope twisting in his chest until it feels like he could sing an opera and like he's drowning at the same time. "Would you like to go with me?"

Dean bites the inside of his cheek as he waits for Castiel's answer. He clutches his thighs, leaning backward slightly to prepare for rejection. Castiel looks away from Dean, staring at a nearby bush instead. His eyes follow the path of a bumble bee, a soft smile on his lips. Dean takes note of this fondness and tries to calm his heart.

"Yes, I would like to go to the dance with you, Dean."

Relief floods through Dean, drowns his nerves, unleashes his tension. His muscles buzz and he fist pumps the air. He sighs loudly, standing and shaking out his feet. Castiel watches him, laughing silently to himself. Dean looks down at him, a giant grin on his face.

"Pick you up at 5 for dinner beforehand?" Dean asks.

Castiel nods, still laughing. "Sounds good."

Dean bounces on his toes for a second. "Great, I'll message you on Facebook tonight. Talk to you later."

Dean turns on his heel to walk away so he can share the news and to not freak Cas out with his excitement. He stops mid-turn, repositioning himself to plant a quick kiss on Cas's cheek. The freshman jumps, gasping and touching his skin when Dean pulls back.

Dean chuckles at the bright red color of Cas's cheeks, brushing the freshman's jaw with his thumb. With a quick wink, Dean says, "Damn, Castiel."