Castiel already deeply regretted the bet. Especially when he walked into English class, only to see Dean standing beside the teacher's desk.

Cas, ever the awkward student, promptly tripped over his feet and nearly face-planted into his desk. Dean saw that smooth move, of course, and grinned at him as Cas's face went bright red and he turned his attention to his pencil, which was extremely fascinating all of a sudden.

"You're a little clumsy, aren't you?" Dean guessed, sliding into the seat beside him.

"Not usually, I swear," Castiel admitted. "Just, uh, having an off day, I guess."

"Uh huh," 

"Castiel!" The teacher said suddenly, and Cas jumped a mile. "Could you share your book with Dean today, he hasn't gotten a copy yet."

"Yeah," Cas nodded, trying to force the color off his face. Dean smiled at him.

Okay. Maybe Gabriel had a point. Maybe he could pull this off.

But then Cas dropped the book on the ground, and smashed his head on the desk while trying to grab it.

Smooth, Castiel, smooth.

*****

Gabriel, as a junior, had no classes with anyone in the freshman class. 

He supposed that made his side of the bet more difficult, since he wouldn't see Sam, like, at all.

But then Gabe walked into his Spanish class, and lo and behold, the long haired adorable freshman was sitting front and center in the class.

And for the first time in his life, Gabriel sat in the front row.

"Hello," He began, kicking his feet up on the desk and leaning his chair back.

"Hi," Sam Winchester eyed him warily.

"Name's Gabriel," He held out a hand, and Sam shook it.

"Sam."

"So, Sammoose. Must be a smarty if you're in this class." He shrugged. 

"Just good at languages,"

"Mhmm. Want a lollipop?"

"What?" Gabriel dug a fistful of lollipops out of his pocket.

"Want a lollipop?" Sam reluctantly grabbed one of the lollipops.

"Thanks."

"A cherry man," Gabe grinned smugly. "Good to know." Sam half smiled at him and then focused his attention on the teacher.

Gabriel still has no idea what the teacher said all class. He only paid attention to Sam.

*****

By the time lunch rolled around, Castiel had a decent sized bruise on his head. Whether it was from smashing his head on the desk, or any of the other three skull smashes he had suffered while being distracted by Dean during the day, he wasn't sure. He dropped into the seat next to Charlie and promptly buried his face in his hands with a groan.

"How goes the battle?" She asked. 

"Don't ask," Castiel grumbled in return.

"Hiya Cassie," Gabriel perched on the table beside him. "Can you feel my victory already? I can. Tastes like cherry lollipops." Castiel dropped his hands and glanced up to glare at his brother. Stupid Gabriel. It was all his fault Castiel was in this mess to begin with. Gabriel's smug grin only widened. "Nice bruise. Did you ask hot stuff out and he punched you?" The glare intensified.

"It's probably from the locker he hit in the hallway," Anna guessed, sitting across from them, Balthazar and Hannah following suit. "Slammed right into it and ate dirt on the floor."

"I was gonna say the sprinkler he landed on in gym," Balthazar countered. "How many cracks to the skull have you taken today Cassie?"

"Too many," He grumbled. Hannah held up a hand.

"How many fingers am I holding up?" She asked.

"I don't have a concussion, Hannah."

"Yeah, but I forgot what number comes after two, help a sister out."

"Three, darling, it's three," Balthazar insisted. 

"THREE! RIGHT! THAT'S IT."

"So why is Cassie clumsy today?" Anna questioned.

"There's two new guys at school," Charlie explained. "And these two flipped out and made a bet about asking them out."

"So now every time I see new guy, I crash into something and make a fool of myself," Castiel went on. "Wonderful start."

"But here's the kicker," Gabriel went on. "Guess what new guys names are." Their siblings thought for a moment.

"Jughead," Hannah guessed.

"Gaylord," Balthazar said hopefully.

"Something more satanic than Lucifer?" Anna said.

"Sam and Dean Winchester," Castiel whispered. Their eyes widened.

"No freaking way," Balthazar declared.

"No wonder you two made a bet," Hannah offered.

"Wait, does this mean you're trying to screw guys with the same name as your childhood toys? That's messed up."

"We are NOT-" Castiel started.

"Bitch please, like you didn't have the hots for Jessica Rabbit or Malibu Barbie?" Gabriel countered.

"No, I didn't," Balthazar objected. "I don't have the hots for people. People have the hots for ME. I just indulge their fantasies."

"We know, the house has thin walls," Hannah reminded him. 

"Well at least I don't have to make bets with my siblings to get a date. I just open the door and let somebody waltz in." Anna rolled her eyes.

"And you call ME the whore-" She muttered.

"No, darling, you're the slut, I'm the whore, Gabriel is the hooker, Lucifer is the pimp, Hannah is the bodyguard, and Michael and Castiel are the only ones smart enough to be working somewhere outside the porn industry."

"Hey!" Hannah objected. "I can be much more useful than a bodyguard."

"Well you're still too young to be a stripper so-"

"I was thinking I'd be in charge of the costumes."

"Wait a second, that's a great idea." Balthazar pondered it for a moment. "You could dress Luci in all the greatest pimp fashions."

"Absolutely not," Anna said. "After what you two have already done to my outfits in the past, I forbid Hannah to dress anyone." Hannah shrugged.

"I can't help that Balthazar and you are the same dress size. Believe me, things would be a LOT simpler if he fit into my clothes."

"Oh, how I've tried," Balthazar sighed. "We should break into Aunt Amara's house and steal some skirts or something though."

"Dude. YES." Hannah grabbed a notebook and started sketching a blueprint of their aunt's apartment. "Cassie come here, help us pull off a way to get into her house undetected."

"That's impossible. Aunt Amara is like one of those mean dogs guarding a junkyard." Cas insisted. "You'd have better luck-" He was cut off as Charlie slapped him on the arm hard enough to bruise, and then flailed wildly to slap him some more. "Charlie what the-"

"LOOK." She ordered, directing his attention to who was currently walking through the lunch line. Jo Harvelle, golden hair shining, looked like every bit of the beautiful badass she was as she walked, even while carrying a tray loaded with mystery meat and expired chocolate milk. Charlie had had a crush on that girl since forever, yet since Jo was so mysterious in her ways, Charlie still wasn't even sure if she had a shot. For all they knew, Jo was straight. 

But then Cas stopped paying attention to Jo, because walking next to her and chatting up a storm with the Harvelle, was Dean Winchester. He was smiling, and Sam trailed close behind him, scanning the cafeteria warily. But there was something about the ease between Dean and Jo that made Charlie's flailing understandable.

"No," Cas shook his head. "Nope."

"They BETTER NOT." Charlie practically hissed the words and Gabriel let out a low whistle.

"Welp, looks like you're out of luck, little bro," He declared. "If he's sitting with Harvelle, he's definitely straight and therefore, I should be taking my bet to one of you guys," He pointed a spoon at Balthazar, Anna, and Hannah, who all shook their heads. There were many unspoken rules at the Novak household, everything from 'Never tell dad what we did' to 'Never leave Balthazar unattended when there was any sort of alcohol in the house', but one of the biggest and most important rules was that they didn't go after each others crushes, friends, or exes as potential romantic interests. Going after Dean Winchester was a big no no now that Cas had called dibs. They knew better than to try.

"Just because he's sitting with Jo doesn't mean anything," Cas insisted. "For all we know, she could be interested in Sam." Gabriel dropped his spoon, and joined Cas and Charlie in their intense one sided staring match with the table that Jo and the Winchesters brothers were seated at.

"There's only one way to find out for sure," Gabriel said gravely.

"The bet?" Charlie guessed.

"No. You have to ask Jo out."

The shriek of fear that Charlie let out silenced the entire cafeteria, and left Cas wishing he had paid more attention when they'd taught him the Sign Language alphabet.