The Night Dean Winchester Ruined His Date's Prom (But Got Laid Anyway), or How Lyla Durand Learned to Stop Worrying and Love the Bad Boys

The summary: See title.

The warnings: A bit of language. A bit of sex. A bit of violence. But only a bit.

The disclaimer: I do not own the Winchesters. Alas. No profit, etc.

The thanks: On-A-Dare and Lynne, for incredibly helpful betas.


"Hey, Winchester, I got a proposition for you."

Heath Tillman, uninvited and unwelcome, sat down across from Dean at a table in the cafeteria at Washington High School.

"Tillman, I'm getting tired of explaining this. I'm flattered, but you ain't my type."

"Funny," Heath said. He was the golden boy of the school, king of the varsity jacket crowd, and Dean was occasionally overcome with a strong desire to punch him in the eye for no particular reason.

Dean waited a moment, but that seemed to be the extent of Heath's ability to retort. "Yeah?"

Heath leaned forward, slightly. "Hundred bucks says you can't get Lyla Durand to agree to go to the prom with you."

Almost instinctively, they both turned to look over at where Lyla was sitting with several other cheerleaders. She wasn't the prettiest girl at WHS, or the most popular, or the smartest, or the most anything, really. But if you averaged the categories together, she won hands down.

She'd had some kind of long distance college boyfriend, but that had apparently gone belly up just before the Winchesters moved here after Christmas. Bradley something, Dean thought. And then he mysteriously vanished or something in March. Dean kind of suspected that the mystery could be summed up he wanted the hell out of this town, which Dean could understand. Nothing about it suggested it was the sort of "mysteriously vanished" that the Winchesters looked into.

Dean knew far more than he cared to about WHS gossip because his lab partner never shut the hell up about it. Dean paid attention in his science classes – you never knew when you were gonna need to know how to make something blow up, and understanding physics didn't exactly hurt when your life frequently depended on getting a projectile to hit the thing you were aiming it at. (He was careful to miss a few questions on the tests – he didn't want anyone thinking he was some kind of geek like Sam. But only a few – let your grades get too low, and teachers wanted to talk too your parents.)

"What do you say?" Heath asked, and Dean looked back at him.

The thing about Lyla was that while she might not have a boyfriend, a girl like that probably had a prom date already, with the Big Event less than two weeks away. "You sure she's even still free?"

"She's turned three guys down," Heath said.

"Yeah?" Dean asked. "You one of them?"

Heath colored slightly and Dean had his answer. "Deal or no?" Heath asked curtly.

Dean looks back at Lyla. "Hundred bucks?"


"If she agrees to go to the prom with me?"


Dean shrugs. "What the hell? Deal."


Lyla Durand had spent the last eighteen years doing what she was supposed to do. Or what people told her she was supposed to do. She was a cheerleader, class secretary, a soprano in the school choir, and an honor roll student. She was always cheerful, kind, willing to help out, and a joy to have in class.

There were days she was pretty sure high school was going to kill her before it was all over.

This was one of those days, an exhausting minefield of things that only matter to teenaged girls, and stepping in the wrong place is social suicide. A day of trying to remember who was – and wasn't – speaking to whom this week, or what she was expected to like, dislike, know about, feign ignorance of, or ignore.

She was sitting, now, on the low wall in front of the school, waiting for her dad, and trying to look like she was working on her French homework.

"You mind?"

Lyla looked up to see Dean Winchester indicating the section of wall next to the one she was sitting on. She was surprised enough that by the question that it took her just a second too long to reply. "Ah, no."

Dean dropped almost gracefully onto the wall, and Lyla tried not to be too obvious about the fact that she was watching him. He was a puzzle. She had gone to school with the same people since she was five. And while there had been occasional departures or arrivals, by second semester of senior year, there were not any other puzzles left in her class.

He had pretty much kept to himself, though Lyla had occasionally looked up to find him watching her. When she caught him at it, he didn't look away or seem embarrassed, just grinned at her and waited for her to be the one to look away.

Lyla was not entirely certain that it wasn't a sin to have a boy smile at her like that.

"Are you waiting for someone?" Lyla asked, mostly because she felt like someone was supposed to say something.

"Not really," Dean said. "I was kind of looking for you."

"For me? Why?"

"There's a rumor going around you've turned down like a dozen guys for the prom. Wanted to know if it was true."

Lyla laughed, a little. "Only three."

"You mind my asking why?"

"Um," she said, suddenly very self-conscious. "Well, Rodney's a jerk. And Jason's hands wander. And Heath is a jerk whose hands wander."

"Fair enough," Dean said. "So would you maybe want to go with me?"

"To the prom?" Lyla asked.

He leaned forward and fixed her with very green eyes. "Yeah. To the prom. With me."

Lyla could think of any number of reasons to say no. She had no idea why he was asking; they'd spoken maybe three times, and she'd never seen him attend so much as a pep rally. (Not that she looked for him at pep rallies, of course.) She knew almost nothing about him. She had no idea what her friends would think about it. And she didn't get the feeling he was the sort of guy her parents would be thrilled about her bringing home, either.

But she was tired of being reliable little Lyla, always trying to do and say and be the right thing, tired of worrying about what everyone would think if she got something wrong.

On another day, she might have turned him down. But on that day, she heard herself say, "sure," even before she had quite decided to accept.

Dean smiled. No, Dean grinned. "So I'll pick you up at seven."


Her father's blue Volvo pulled into the school parking lot, and Lyla picked up her bag. "That's my ride," she said, wishing that her dad had been as late as he usually was. Dean nodded. "So, um," Lyla continued, as her father pulled up to the curb, "I guess I'll see you in class."

Dean nodded again. He waited until she had her hand on the car door – till there was no way her dad wouldn't notice – before he caught her arm and then kissed her. "See you 'round, sweetheart," he said, and walked off.


"Easiest hundred bucks ever," Dean said to Sam that night.

Sam was sitting at the kitchen table in their shoebox of a rental house, surrounded by his books and working methodically through his homework assignments. Dean was fixing dinner – hot dogs and Easy Mac.

"Did you hear me, Sammy?" Dean asked, and Sam sighed and looked up from his math homework. "Easiest hundred bucks ever."

"A hundred bucks? To take a girl to the prom?" Sam asked.

"Yeah. She's pretty hot, too, so it's not even like it's gonna completely suck."

Sam nodded, but his expression was one Dean recognized. It meant, loosely translated, Okay, I have something to tell you, and I'm pretty sure you won't like it, but I'm going to tell you anyway, just as soon as I figure out how.

"What?" Dean demanded.

"I think you got tricked," Sam said, slowly. "Or something."


"Well, I think . . . I think you kind of lose that bet even if you win," Sam said.

"How the hell does that work, Sammy?" Dean asked.

"You know, it's probably going to cost you more than $100 to go to the prom – once you buy tickets and rent a tux or get a suit or whatever, and buy your date a corsage—"

"A corsage? Screw that idea."

"I think they kind of expect it," Sam said.

"Well, she can just stop expecting it," Dean said, slamming food onto plates and bringing dinner over to the table. "Anyway, what makes you an expert on the prom?"

Sam shrugged. "How many times have we watched Pretty in Pink in some motel room or another?"

"A hell of a lot more than we ever have to admit to, Sammy."

"I'm sorry, Dean."

Dean didn't reply, just started in on his food. He was almost done with his third hot dog when he grinned.

"What?" Sam asked.

"This whole prom thing? No problem."

"How?" Sam asked, cautiously.

"Tillman bet me I couldn't get her to agree to go with me. She already has. Everything else is just . . . details, right? Pass the relish."


When Lyla was eight years old, she stood on her front porch and watched her neighbor and favorite babysitter leave for the prom. Of course, that had been 1987, and it had actually been kind of hard to see Amy amid all the masses of hair and ruffles. Lyla, though, had thought she looked like a princess, and she had started planning for her own prom in that moment.

Of course, she'd gone with Bradley to his last year, but that was different. That was Bradley's prom. This one was hers.

She'd had to make a couple of substitutions. The dress selection was slightly picked over by the time she went shopping, and she hadn't been able to find her dream dress, which would have been pale pink and vaguely evocative of both a princess and a ballerina. But the red looked good on her, at least, and she had found the perfect slightly tiara-like rhinestone headband.

At precisely 6:57, she checked her handbag one last time to make sure she had everything, took one last look in the mirror, and then sat down on her bed to wait for Dean. That way, she could make her grand entrance down the front stairs.

At 7:06, she got up to look out the window and see if he was there yet. And again at 7:10, and 7:12.

At 7:15, she asked her mother if maybe Dean had called to say he was running a little late. He hadn't.

At 7:19, she looked out the window again.

At 7:23, she went downstairs, because she could see more of the street from the living room window, and sat on the couch.

At 7:25, she got up to look out the window.

At 7:31, she asked her mother is she was sure Dean hadn't called to say he was running late. Her mother was positive.

At 7:37, she moved one of the living room chairs over next to the window, so she could look out every 45 seconds or so without having to keep getting up.

At 7:45, she asked her father if there was anything on the news about a tragic accident involving a WHS student on his way to the prom. There wasn't.

At 7:49, she went out into the front yard and over to the curb, and looked as far as she could see in both directions. Nothing.

At 7:52, Lyla accepted that the unthinkable had happened. She had been stood up for the senior prom. She went back into the house and straight up to her room, not in the mood for either her mother's sympathy or her father's I told you that boy was trouble.

And at 7:55, a car pulled into the driveway, bass-thumping, engine rumbling, and horn blaring.

Lyla looked out the window. Her wayward prom date had arrived.


In the driveway of Lyla's cookie cutter suburban house, Dean sounded the horn again. It was almost 8:00; she had to be ready by now, right? He honked one more time and then sighed. He should have figured she'd be the ring-the-doorbell type. Dean killed the engine and went up to the house.

He didn't actually have to ring the doorbell, though, because the door opened the moment he set foot on the porch. Lyla did not exactly look thrilled to see him.

She did, however, look pretty hot, if maybe a little overdone. The crown was definitely over the top, but the dress was red and pretty slinky, two things Dean approved of. Better, certainly, than cotton candy fluff pink or pseudo-wedding gown white.

"You ready?" he asked.

"What the hell are you wearing?" Lyla demanded.

Dean looked down at his outfit and back up at her. He thought the answer was pretty obvious. Okay, so it wasn't exactly typical prom attire, but the jeans were almost new and the shirt had only been mended once, and he cleaned both his boots and the leather jacket. This was as close to dressed up as Dean got. "Clothes. We going?"

Lyla's chin went up. "My parents want to meet you."

"I don't really meet parents," he said. But he stepped into the Durands' front hall anyway.

"Lyla, honey, is that Dean?" her mother asked, coming in with a camera in hand. "I want to take some pictures before you—" she stopped, smile fading, as she caught sight of her only daughter's prom date.

"Nice to meet you, Mrs. Durand," Dean said, and held out a hand. He counted to seven before she took it (his record was eleven). "Where did you want us to pose?"

Mrs. Durand, with a very uncertain expression, put them in front of the fireplace, and took what was probably the bare minimum of pictures she thought she could take without being rude. She took a lot more of Lyla by herself, while Mr. Durand watched with unmistakable disapproval of the whole affair. He then pulled Dean aside for the you better have her home by midnight, boy speech. Dean saluted, and offered Lyla his arm.

He could totally do the prom date shit if he had to.

Lyla got into the Impala reluctantly and gingerly, like she was afraid of catching something from it, or getting her dress dirty. Dean was insulted – that car was never less than perfectly clean. Okay, so occasionally someone had bled all over one of the seats, but they had always cleaned it up immediately afterwards.

"Nice car," Lyla said, though he got the feeling she wasn't even trying to sound like she meant it.

"Thanks." No matter what she thought of it, getting to borrow the car was always a big deal. Lately Dad had started to talk about them maybe needing to get a second one, and Dean was all for that. In the meantime, he didn't get to take the car out alone all that much.

He handed Lyla a plastic-wrapped peanut butter sandwich and a can of coke. "What are these for?" she asked.

"Dinner," he said. Dean started the engine and, to the dulcet tones of "You Shook Me All Night Long," they headed for the high school.


Lyla sat in the passenger seat of what was probably the oldest, loudest, least reputable vehicle she had ever ridden in, holding a sandwich and a small black purse with nothing much in it. She thanked God that the music was too loud for conversation – the only things she could think of to say were not the sort of things it was wise to say to the guy driving the car you're stuck in.

The high school parking lot was already pretty full. Not surprising – they were over an hour late. Lyla was surprised, however, when instead of parking with the other cars, Dean opted to drive around to the back of the building.

"Ready?" he asked, killing both the engine and the ear-splitting retro rock.

"For what?" she asked, warily.

"The prom? Kind of the reason we're here, right?"

"Aren't we kind of far from the door?" she asked, tossing her uneaten sandwich onto the dashboard.

"Not the one we're using."

"What? Why?" she asked, and then the pieces snapped into place. "Oh my God, you didn't buy tickets."

"Neither did you," Dean pointed out, and got out of the car. She was a little surprised when he came around to open her door for her. Though not surprised enough to actually get out of the car.

"Dean. I cannot crash the senior prom."

"Sure you can. Just follow my lead, sweetheart."

Lyla sighed and finally took the hand he offered. "You are gonna get me in so much trouble."

"As much as you let me," he said.

Lyla decided against asking what exactly he meant by that.

She also decided against asking why he knew how to sneak into the girls' locker room.

Which was probably for the best.


Any other year, the more-than-an-hour-late arrival of someone like Lyla Durand, accompanied by a guy in jeans and leather jacket, and entering through one of the locker rooms would have been The Story to come out of the senior prom.

That year, however, Shannon Costa had already arrived on the tuxedo-clad arm of Bradley Pritchard, Lyla's missing ex-boyfriend.

No one had seen Bradley since the he came home from college for Spring Break. He had gone to take a walk, his mother said, and he had simply never come back. People searched, but no one found him. He hadn't turned back up at school. His parents, supposedly, occasionally found a letter from him on their front porch, assuring them he was fine, but providing no details.

The rumors flew. He had joined the army or a circus or a cult. He had gone insane and been locked up, or gotten arrested. He'd gotten sick, or been in an accident, or gone to rehab.

But one thing (possibly the only thing) that no one had suggested was that he would turn up at the prom with Shannon Costa. Because for all that she was the Queen of both the school and the prom, and for all she'd thrown herself at him over the years . . . well, he had never seemed to actually like her all that much.

Dean was privy to some of that history thanks to his gossipy lab partner, though he wouldn't have been able to pick Bradley Pritchard out of a lineup. He was pretty sure that his date was upset about something, though. She was frowning and tense, and he didn't think it was because they just made their grand entrance through a back door. Or because he was a little late. And, okay, maybe he should have sprung for burgers instead of getting Sam to make sandwiches, but come on, it wasn't like girls ate on dates, anyway.

"You okay?" he asked.

"I'm fine, thanks," she said, a little too quickly.

Okay, this was awkward. Dean didn't really believe her, but he also didn't want to run the risk of her suddenly getting all emotional and girl-like if he pressed. So he changed the subject.

"See, sweetheart," he said, "I told you that you could manage the sneaking in thing."

"I really wish you'd stop calling me that."

"Well, I didn't think we were to the 'baby' stage of things, yet."

"Oh, we're definitely not," she said. "But you could call me 'Lyla.'"

"Sure thing, sweetheart," he said, looking around the gym. It could be worse, he decided. He had no idea why there were quite so many glitter-encrusted stars hanging from the ceiling, and the music sucked, but hey, that was to be expected. Lyla, he noticed, looked better than most of the other girls here. So far, it was shaping up to be a less than terrible night.

"You want something to drink?" he asked.


"Be right back." But first he needed to find Heath Tillman.

Somebody owed him a hundred bucks.


Shannon waited about five seconds before she excused herself from her date and came over to talk to Lyla.

"Hey, Lyla, there are you are. I didn't see you come in."

Lyla suspected her smile looked about as forced as it felt. "Guess you missed it," she said. "You look nice, Shannon."

"Thank you." Shannon smoothed non-existent wrinkles out of a pink ballgown-like dress. "Bradley seems to like it; he just can't keep his hands off me tonight," she said, lowering her voice to a conspiratorial whisper.

"I'm surprised to see him, honestly. Just, you know, given that no one has heard from him for a while," Lyla said.

"Well, he wouldn't have missed being my prom date for the world," Shannon said. And then, with markedly false concern, asked, "You don't mind that he came with me, do you, Lyla?"

"No. Why would I? He and I broke up, Shannon. Months ago. And I'm glad he's okay, we've all been worried, but I really don't have any say in how he spends his time."

Shannon's eyes narrowed. Lyla had a feeling she was not going to like whatever came next. Shannon's perfect prom queen smile never wavered, though.

"That's so sweet of you. And I think it's really great that you were brave enough to actually show up tonight, Lyla."


"Well, yeah. I mean, if my, um . . ." Shannon paused, and looked over at Dean, standing by the punch bowl, and then back at Lyla, ". . . well, let's call him your 'date,' for lack of a better word. If my 'date' had only asked me to the prom because of a hundred dollar bet? I wouldn't have been able to ever show my face at school again, never mind have the nerve to actually show up at the prom with him."

"Shannon, what the hell are you talking about?"

"Didn't you know? Everyone else does. Heath Tillman bet Dean Winchester a hundred dollars that he couldn't get you to go to the prom with him. I guess you're easier than Heath thought."


Dean wasn't exactly surprised when Tillman didn't have the cash on him. Annoyed, but not surprised. He took fifty bucks as a down payment, though, and that wasn't a bad start.

Dean was also not surprised to find that some idiot had spiked the punch, though he was a little pissed that they did such a bad job of it. Used some nasty shit vodka, and not nearly enough of it.

He was willing to bet that Lyla wasn't much of a drinker. Fortunately, he knew, thanks to some earlier experimentation, that if you hit the soda machine in the cafeteria just right, it would dispense orange soda without the use of quarters.

The halls were pretty deserted once he got away from the gym. He did run into one guy on his way back who looked a little . . . wrong. It was hot and loud in the gym, though, so maybe the guy just sick and needed air.

Lyla was still where he left her, talking to some blonde in a dress that was too damn pink even for Barbie. Dean couldn't remember her name – Sharon, maybe – but she smiled when she saw him.

(It was the sort of smile that made Dean wish he was armed – things that smiled like that were almost always evil.)

"Hi, Dean," she said. "We were just talking about you."

"Hi, Sharon," he said.

"It's Shannon," she corrected. "Well, I'll leave you two alone. Bye, Lyla."

Shannon flounced off.

Dean held out the can of soda. "Some idiot spiked the punch, so I thought you'd probably rather have this."

Lyla didn't thank him. She didn't take the soda, either.

"Take me home," she said, and oh, Christ, was she about to cry? He hated it when they cried. "Now."

"What? We just got here. Don't you wanna do anything—"

"Did you really think I wasn't going to find out?"

"Find out what?"

"About you and Heath and your bet."

Oh, shit.

Honestly? It had never occurred to him that she would find out. Or, well, it had never occurred to him to wonder if she would find out.

"Hey, look, I —"

"I'm not interested. You have completely humiliated me, and I just want you to take me home, and not talk to me on the way." She turned, and walked out of the gym.

Dean watched her go, and then opened the soda. She looked like she maybe needed a minute to calm down.

Possibly longer than that.


Lyla stood by her date's hideous car, and tried not to cry. There was no way she was going to let that bastard see how upset she was.

She considered kicking the tires, but given that she had on open-toed, high-heeled shoes, she'd probably just wind up hurting herself.

"Hey, there, Lyla," someone said, and she turned to find Bradley standing by the door, leaned up against the wall and watching her. "Where's your date?"

"Around," she said, walking over to talk to him. "Where's yours?"

"Shannon? Inside being queen of the prom," he said. "I'd much rather be out here with you." He reached one hand out to touch her hair, and Lyla jerked away.

"Bradley, don't," she said. "We broke up, remember?"

"Maybe we shouldn't have. You are all I ever think about, Lyla."

"Which is why you're at the prom with Shannon? After the whole disappearing act, and being gone for more than two months? Everyone's been worried, where have you been?"

Bradley shrugged. "I didn't have a lot of choice in the matter. I kind of owed her. But I'm done with her now." He reached out to Lyla again. "Have you been worried about me, Lyla?"

She stepped away, shrugging lightly. "Sure, I guess. I mean, no one even knew if you were alive or dead."

"I am," he said, which wasn't really an answer to that statement. But before Lyla could ask what he meant, he continued, "And it's going to be better this time, Lyla. I promise."

"Bradley, cut it out," she said, but his hand closed on her wrist, and she didn't remember her ex-boyfriend being that strong. "You're hurting me."

"It's going to be better this time," he said, again, and something was really wrong here.

"Let go of me, Bradley. Please," she said.

"You have to come with me," he said, and started to pull her away from the wall. "I need you."

Behind her, Lyla heard the truck of a car slam.

"Pretty sure she said to leave her alone," someone said, casual but dangerous.

Lyla's wayward prom date had, once again, arrived.


Did Dean know how to pick them, or what?

"Why don't you mind your own business?" the other guy replied.

"Well," Dean said, amiably, starting to close the gap between them, "that's my date you're molesting, so this kind of is my business."

"Seriously, buddy, you should go. You don't know what you're messing with here."

That was only partly true. Dean was about 90% sure he was dealing with the guy he'd seen in the hall earlier. He was more than 90% sure that whatever was wrong with this guy, it was a hell of a lot more than needing some air.

Of course, that didn't tell him exactly what he was dealing with, though he had it narrowed down some.

"Well, neither do you," Dean said.

The thing about a gun loaded with silver bullets was that it was the ideal weapon for relatively few things. But it was also not a bad weapon for a lot of things. Most weird shit was at least a little bothered by silver. Or at least by bullets.

And if he was just dealing with some seriously messed up human being, well, pulling a gun was usually a good way to make the guy back down.

"Okay," said Lyla, "I think maybe everyone just needs to calm down a little. Or a lot. Or someone's going to get hurt."

"Just let her go," Dean says. "And walk away."

The thing holding onto her arm didn't let her go, just pulled her around so that she was between him and Dean. Damn. Dad was gonna be pissed if he wound up shooting his prom date, even accidentally.

"Please, Bradley," Lyla said.

"No. She's mine," Bradley said to Dean. And then, to Lyla, repeated, "You're mine."

Christ, the lovesick ones were the worst.

"You put the gun down and leave," Bradley told Dean.

Dean assessed the situation. Putting the gun down probably got everyone good and dead. Then again, the hand Bradley had just moved to Lyla's neck looked like it could make her good and dead, too.

Dean held his hand up, fingers clearly away from the trigger, and slowly began dropping into a crouch to set the gun on the ground. He never took his eyes off Bradley, though, and he was ready for it when Bradley shoved Lyla into the wall and jumped at him.

That was what the silver knife up his sleeve was for.

If his date hadn't recovered her footing and tried to help him, it quite possibly would have ended right there. But instead she tried to pull Bradley away from Dean, and Dean wound up stabbing him in the shoulder instead of the chest. Bradley gave an inhuman cry and took off into the woods behind the high school, moving faster than he should have been able to.

Dean looked up at his shell-shocked date. "So I take it that was your ex-boyfriend?"

She managed to nod.

"And was he a zombie when you two were together, or did that happen later on?"