If you asked Sam, he would say that Dean's absolute determination to win over Castiel Novak was purely based on the "you always want what you can't have" principle.

If you asked Dean, he would say because she was freaking gorgeous, and brilliant to boot.

"Tonight's the night, Sammy," Dean said confidently, straightening his bow tie in the mirror, "I can feel it."

Sam just rolled his eyes from where he was sitting on his bed, nose in a book, as usual, "She's so out of your league, Dean. And contrary to what you read in Playboy, just because you dress up in a tux does not mean she's suddenly going to fall in love with you."

Dean chortled, picking up the masquerade mask from the dresser and sliding it around his head. He took a moment to admire his reflection, the black lacquer finish swirled with emerald green flushing out the color of his eyes.

"Oh Sammy, ye of little faith."

Sam just sighed and shook his head, turning the page.

"Now, remember Sammy, just because you're an underclassmen and can't go to the party doesn't mean you have to have a dull Halloween. Eat some candy! Watch some porn!"

"Dean," Sam groaned, "Will you just leave already?"

Dean just laughed as he stepped out the door of their dorm, smoothing his lapels as he headed downstairs to the main hall.

"Woah, Winchester, lookin' good," Jo complimented, and Dean turned to grin at her as she came from the direction of the girl's dorms, stunning in a vivid red dress and matching mask.

"Mmm, right back at cha, wow," Dean smiled, looking her up and down slowly.

She smacked him playfully before hooking her arm through his and cozying up to his side, "Which means you'll have no problem escorting me downstairs like a gentleman, right?"

"It would be my honor, fair lady," Dean purred smoothly, and Jo grinned, a faint blush flushing around the corners of her mask.

"They really went all out this year," Jo commented as they entered the hall, taking in the lavish decorations and the live orchestra that was already playing lively classical peices.

"Glad to see our tuition used for something practical," Dean murmured, and Jo chortled.

"Hey, Dean, what's up?"

"Jo! You look great!"

"Nice masks, you guys."

By the time they hit the drink table, they had seen almost every friend and acquaintance they knew, and Jo smiled as Dean scanned the crowd as he got punch from the punch bowl for them both.

"No sign of Cas, huh?" she teased, and Dean gave her a look as he handed her her glass.

"I don't know, any sign of Ash?" he quipped back, and she groaned.

"Don't remind me. The guy's practically a puppy."

Dean chortled, taking a drink (not bad, but maybe he'd spike the punch bowl later) when Jo tapped his arm, nodding at a point behind him. He turned, and froze when he saw Castiel.

She was stunning. Simple, long black dress that was elegant without overdoing it, and an ornate, silver mask that made her blue eyes practically glow.

"Pick up your jaw, Winchester," Jo nudged, and Dean snapped out of it, grabbing another glass and filling it before heading toward her.

"Go get 'em, tiger!" Jo encouraged, but Dean barely heard her as he shifted his way through the crowd.

"Hi, Cas," he said, finally reaching her, and Cas smiled.

"Hello, Dean."

"Aw, look, the monkey's wearing a tux."

"Hello, Meg," Dean said dryly, glaring at her, "Sorry, didn't see you there, you blend right in with the decorations. Must feel real homey to you."

"You're hilarious, Dean. Real stand-up material," Meg purred back, shifting in her dark blue, low-cut dress, eyes narrowed behind her gold mask.

"Meg," Castiel said gently, giving her a look and Meg fell silent, giving Cas a pointed look in return.

"I came to offer you a drink," Dean turned back to Castiel, holding one of the glasses out for her.

"Thank you, Dean," Cas accepted it gracefully, while Meg scoffed.

"What, no drink for me, Dean?" Meg couldn't help but jab, and Dean glared.

"If I ever offer you a drink, it'll be poisoned," he said flatly, "Shouldn't you be out there sucking some souls or something?"

"You know what, I should," she sneered, "Maybe I'll just take a trip upstairs and start with your precious baby brother."

Meg sauntered off before Dean could answer, giving Castiel a warning look as she disappeared into the crowd.

Cas sighed heavily, looking into the bottom of her glass.

"I wish you wouldn't fight so," she said quietly, and Dean deflated a little.

Despite his best efforts to convince her otherwise, Castiel liked Meg. The two were roommates, so Dean supposed it made sense to want to like the girl you were living with, but he just couldn't understand it.

"Sorry, Cas," he apologized anyway, stepping a bit closer as the music picked up the volume, a snappy song making it a little harder for casual conversation.

"You look beautiful tonight," he said, and he could see Cas flush behind her mask, embarrassed by the compliment.

"As do you, Dean," she said in return, "That mask is very beautiful, it suits you perfectly."

"Jo helped me pick it out," he confessed with a smile, "The girl's got style, I gotta admit."

"Indeed," Cas answered simply, and Dean smiled. She looked so lovely, her hair artfully curled and hanging loose around her shoulders, and Dean very much wanted to tangle his fingers in it and kiss her silly.

"Did you attend with Joanna as your date?" Castiel asked, and Dean shook his head.

"Nah, just hanging out. Thought I'd fly solo this year, see how it goes."

"Oh? And how is it going?"

"Well," Dean smiled warmly, "It means I can come over here and talk to you all night without a jealous date, so I guess pretty well so far."

Castiel blushed a little deeper and took a sip from her glass, clearly unsure of how to respond.

They were saved by the appearance of Chuck, who suddenly appeared at Dean's elbow like he had been magicked.

"Hey guys," he said, looking sharp with his grey-patterned mask, "How are things?"

"Heya Chuck," Dean clapped him on the shoulder, "Good, man, how about you?"

"Good, good," Chuck nodded, fidgety as always, "Think I bombed that math test yesterday, though."

"I'm sure you did fine, Chuck," Castiel assured him, and Chuck smiled at her.

"That's nice thinking Cas, but I doubt it. Guess we'll see come Monday, eh?" he laughed nervously, and Cas and Dean nodded politely.

All three of them looked up when the music changed, the previous upbeat song turning into a slow, mellow tune.

"I love this piece," Castiel sighed, cocking her head to listen, and Dean knew an opportunity when he saw one.

"Chuck, buddy, hold our drinks for a minute, won't you?" Dean said, and Chuck nodded, holding his hands out.

"Castiel, may I have this dance?" Dean asked formally with a little bow, offering out his hand. Cas considered it for a moment and Dean panicked that she was going to leave him standing there like a total ass.

"You may," she finally said instead, allowing Chuck to take her glass as she slid her hand into his.

Dean felt butterflies in his stomach as he lead her out onto the dance floor, where many other couples were already standing, swaying in time to the music.

Dean pulled her close, but behaved himself, keeping his hand at a respectable place on her back as the other held her hand gently.

There was silence for a few minutes, just the gentle roll of the music and their patterned swaying; Cas's electric blue eyes staring straight into his unflinchingly.

"You really do look beautiful tonight, Cas," Dean leaned in to say quietly, and Cas gave him a small smile.

"You don't give up, do you?" she said unexpectedly, and Dean smiled.

"Nope."

"Dean..." Cas began, clearly gearing up to let him down gently again, but Dean cut in.

"What's so terrible about the idea of being with me, Cas?" he asked, "What have you got to lose, hm?"

"My dignity, if your reputation is anything to go by," she answered honestly, and Dean balked.

He'd been around a bit, sure. Dean was a flirt, he couldn't really help it, but he hadn't realized it had become some kind of mark of shame to have been with him.

"Yeah, well, don't believe everything you hear," he said lamely instead, actually a little hurt. He looked away from her, eyes going instead to the surrounding crowd.

He was surprised to feel Cas's hand move from his shoulder to the side of his face, cupping his cheek gently and turning his eyes back to her.

"I've hurt your feelings," she said simply, looking upset herself, "I'm sorry."

Dean gave her a small smile, "At least you're honest. I can always trust you for that, Cas, so I can't complain too much."

"Can I trust you to be the same for me?"

Dean paused at the question, looking searchingly into Cas's eyes.

"Yeah," he said honestly, a little surprised himself at how much he disliked the idea of lying to her, "Yeah, Cas. I don't want to lie to you."

"Then please tell me, why me?" she asked quietly, "Why do you like me so much?"

Dean felt the impulse to laugh at how forward a question it was, but refrained, the seriousness in Cas's eyes telling him just how important his answer was going to be here.

The truth was, he wasn't entirely sure himself. Castiel wasn't exactly his usual type; she was exceptionally brainy, quiet, shy. More his brother's type, if Sammy were old enough for her. Dean's girlfriends were usually... well, Rhonda Hurley. Confident, athletic, brash, and flirty, just like him.

He'd been asking himself the same question, "Why Cas?" pretty much since he met her.

"I don't really know," he said truthfully after a moment, "I just know you're... special. You're brilliant, and funny, even though I know you usually don't mean to be, which makes you even funnier."

He smiled, giving her hand a gentle squeeze, "You're sweet and thoughtful and just... nice. I don't know, Cas, I just really like you."

Dean felt a moment of panic when he it looked like Cas's eyes were watering behind her mask, an he had no idea what he had said that could have upset her. She wanted the truth, and that's what it was.

"Cas," he started with concern, but didn't get farther than that before Cas was pushing up on her toes to kiss him.

Dean was momentarily stunned, but pulled himself together in an instant, wrapping his arm tighter around her and leaning down into the kiss, her hand still cupping his face.

He was disappointed when her lips parted from his a moment later, Cas pulling back to look at him seriously, "I believe you," she said, and Dean raised his eyebrows.

"So..." he prompted gently, "Does this mean...?"

"It means you get to kiss me again, if you want," she murmured, turning pink around the corners of her mask, and Dean grinned, stepping back but keeping her hand in his.

"Come on," he said, thrilled to his bones, already planning on wrapping her in his tuxedo jacket and taking her outside, where the light of the moon was promising to make her glow beautifully, "If I'm gonna kiss you, I want you all to myself."

Castiel blushed deeper, but smiled, allowing him to lead them both in the direction of the doors.

Take that, Sammy.