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cruel to be kind

Summary:

ian is an aggressively gay kid in a waspy private school, karen is his stepsister who only kisses girls at parties when she's drunk, mandy is the skanky girl from the other side of the tracks, and mickey just wants to smoke and listen to 70s punk.

or, the 10 things i hate about you au nobody asked for.

Notes:

i own nothing in this story, including the various 10 things quotes sprinkled in #plsdontsueme. anyway WHOS PSYCHED 4 SEASON 5 I AM

Chapter 1: i want you to want me

Chapter Text

“Mickey! Mickey, wake the fuck up, it’s time to go!”

“Chill the fuck out, Mands, I’m up.”

“Well, hurry your ass out the door. Fuckin’ school starts in half an hour.”

Mickey slouches out of his bedroom door, burping. “Didn’t know you were so punctual,” he says. 

“Yeah, well, some of us like to make a good first impression.”

“A good first impression?! Jesus fucking Christ, Mandy, try and be a little more anal. A good first impression, shit,” Mickey said, rolling his eyes.

“Fuck you. You could try a little harder, you know. Wear some clothes that aren’t hideous.” Mickey flipped her off. Maybe he did wear jeans that were a little too baggy, and maybe he should stop cutting the sleeves off of his tank tops, but at least he wasn’t crazy. 

“Yeah, well, speaking of clothes, asshole, put some on.” Mandy made a little shocked noise. 

“Be outside in fifteen or I’m leaving you,” she said, flouncing off in her little bodycon miniskirt, grabbing her combat boots. Maybe her life would be easier if her skirts didn’t make her worry about flashing her uterus at people, and maybe she should wear tops that weren’t a couple sizes too small, but at least she was going to be on time.

“Leaving me? I’m driving you!” Mickey shouted after her.

*****

Mickey pulled up to their school in his beaten up pickup truck slowly, like he was scared of it. “Shit,” he said.

“Yeah,” Mandy replied.

Their new school was the nicest private school in Chicago, way up in the North Side. For two kids who had spent their childhoods doing flashcards on tour buses and dodging drunk drummers, it was a step up. Mickey and Mandy were the two youngest kids of Terry Milkovich, infamous frontman for the Hell’s Angels, the biggest arena rock band of 1987, and Marija Oleynik, his ill-fated muse. Nowadays, she was long dead off a heroin overdose, the band was on their 5th greatest hits tour, and Terry’s new young wife thought it was time to drop the two sullen teenagers from the entourage. So they got sent back to Chicago, where Terry had grown up, to live with his sister Randi in the house he grew up in. The south side wasn’t so weird; even though the Angels stayed in nice hotels and drank expensive liquor, they were just a bunch of guys from the hood who made it big. In fact, in a lot of ways the south side was tamer than life with the Angels was: southsiders didn’t usually have the money to go truly wild. Way weirder was the idea of going to school with a bunch of rich pansies whose parents were in the same tax bracket as the Milkoviches, but spent their money on stocks and home remodeling instead of motorcycles and boob jobs for their increasingly young girlfriends.

For a couple minutes, the two of them just sat there in their car, as blonde girls with designer purses swarmed around them with smartphones on their way to class. “We should go in,” said Mandy, without moving. 

“Yeah, probably,” says Mickey, also sitting completely still.

Finally, Mandy breathed in deeply, squared her shoulders, and picked up her purse. “I’m going,” she said. “Coming?”

“Nah,” said Mickey, lighting a cigarette. “I’m gonna chill for a while.” Mandy rolled her eyes.

“Well, don’t be too late, asshole,” she said, as she swung out of the car door and into the parking lot. Mickey watched her walk towards the building, her black hair and skanky clothing making her stand out among their prissy, chic peers. He took a long drag of his cigarette, turned up his radio — he’d had a new one put in when he got the car, and it was by far the nicest and most expensive part of the entire vehicle — and leaned back in his seat. Fuck high school.

****

Mandy felt herself sticking out like a sore thumb as she stalked the halls of Parker High School, and the more she tried to blend in — walk a little more delicately, smile a little, be more feminine and less trashy — the more she felt like a freak. She was so focused on her status as a white trash new money alien in this sophisticated blue blood world that she walked past the counselor’s office twice before realizing it was where she was supposed to be.

“Um… excuse me? I’m Mandy Milkovich?” she said, poking her head in. 

“Ah, yes yes yes. Please come on in,” said the sweet-looking middle aged woman inside. Mandy awkwardly shut the door and sat down. “Cookie?” said the woman — Ms. Jackson, Mandy read on her nameplate — and held out a plate, and Mandy struggled to maintain eye contact as she realized that sitting right on Ms. Jackson’s desk was a vibrator. A huge vibrator. And not even the kind that could be a neck massager, or could be mistaken for a neck massager — a big, veiny, dick shaped vibrator. Mandy took the plate, staring off into space and feeling somewhat bewildered as she nibbled on the best chocolate chip cookie she’d ever had.  

“Okay, so here’s your schedule, go wait outside and someone should come by to give you a tour, and I hope you just have a lovely day. Now scoot!” said Ms. Jackson, and Mandy found herself picking up all her shit and being swept out of the office, brain still swirling. 

“Okay — bye?” she called out behind her as she shut the door. Normal school was confusing. 

As she left the office, she saw none other than Mickey being escorted in. “Mick?” she asked. “What the fuck?”

“Got caught smoking on school grounds,” he said, rolling his eyes. “Apparently it’s against the rules. Say they’re gonna call my parent and or guardian,” he said, wiggling his eyebrows. Mandy giggled. On tour with the Angels, the only time Terry was ever proud of them for anything remotely resembling schoolwork was when Mickey showed up to tutoring almost blackout drunk at age 14. The tutor had immediately gone to Terry to let him know exactly what his son was getting up to; he had fired her for “bitching about it” and given Mickey a hard clap on the back. “You’re a man now,” he’d said, as Mickey held down vomit. Mandy just heard Ms. Jackson saying “Ah, Mr. Milkovich, something tells me we’ll be seeing a lot of each other,” when someone came up behind her and tapped her on the back. 

“Mandy?”

She whirled around to see a small redheaded girl with a large backpack standing expectantly behind her. “I’m Debbie. I’m giving you a tour.”

“…You’re in high school?” Mandy immediately felt stupid and mean for asking — what if the girl was just a late bloomer? — but Debbie just blushed and said no, she wasn’t.

“Parker starts in sixth grade,” she told Mandy as they started to walk. “I’m an eighth grader this year.”

“…cool.” Mandy rolled her eyes a little behind Debbie’s back as they started to walk down the hall. Of fucking course she would get a fucking infant to give her a tour. 

“So how was Sheila?” Debbie said, laughing a little as she looked over her shoulder at Mandy. 

“Sheila?”

“Oh, Ms. Jackson. I call her Sheila because she’s my stepmother.”

“Wait, what?” 

Debbie smirked. “It’s a long, long story. But yeah, Ms. Jackson is my stepmom.”

“Shit,” Mandy said. “You must have this whole place wired.”

“I mean, I don’t like to brag, but last year I got an A instead of a B- on my biology project because I threatened to leak Mr. Barner’s Fetlife profile to the faculty.” Debbie giggled. “He called himself a naughty little boy who needed a mommy to punish him. And there was, like, more than one photo of him in panties and little skirts.”

Mandy laughed out loud. “Jesus.” She had underestimated this little infant.

“I mean, to be fair, I have four older siblings who got here before me, so they felt it out.”

“For real? I got five older brothers.”

Debbie shudders. “Fuck. At least I have two sisters.” She seems a little uncomfortable swearing, and Mandy thinks she’s adorable. As they walk out into the school’s courtyard, Debbie starts to talk her through the various cliques soaking up the last of Chicago’s warm season, like they’re in some dumb 90s teen movie.

“Anyway, there’s your standard beautiful people. Here’s the coffee kids, the White Rastas, the urban Midwestern cowboys…” 

“What the fuck?” Mandy asked as they passed by a group of boys all dressed in cowboy hats and heeled boots.

“Nobody knows.”

They kept walking, and Debbie stopped near a table full of girls with straightened hair and flat chests. “These are my friends. We’re the 8th grade skanks,” she said, and then, leaning in so they could hear her, “Hey guys!”

“Fuck off Debbie,” says one particularly bitchy looking blonde. Debbie rolls her eyes. 

“Fuck you, too, Holly,” she says, and stomps away. Mandy hurries after her, starting to feel like she’s getting whiplash.

“What the hell? Those are your friends?”

It’s complicated. Last week, I was their god.

“What happened?” said Mandy. Even if most of her knowledge of middle school came from Disney Channel, she had witnessed enough ugly band fights to understand this kind of drama.

“They found out my ‘vintage Chanel’” — here Debbie used air quotes — “was actually from a thrift store.”

“They kicked you out for that?”

“I’ll get them back for it. Don’t worry,” said Debbie, and even though Mandy’s feelings for this situation are more ‘mildly interested’ than worried, she nods.

Debbie starts to say something else, but stops and shouts “Hey, Karen!”, and a head of curly blonde hair spins around, and Mandy’s whole world stops.

Karen is a beautiful girl with a delicate nose and soft, pretty lips and eyes that make Mandy want to get right up close to her. Her hair is long, cascading down her back in these soft little waves like an ocean, and her smile is cute and indulgent while Debbie introduces Mandy to her. She’s Debbie’s stepsister, Ms. Jackson’s daughter — “Yeah, her and a shit-eating sheepfucker,” says Karen, and the stupid profanity coming out of her dainty small mouth makes Mandy want to kiss Karen until her lips get swollen and bruised and her hair is messy and rumpled. 

“Well, I gotta get to first period. See ya, Debs. Nice to meet you…”

“Mandy.”

“Mandy. Right. Have a good first day.” And then she’s gone, in a whirl of blonde and a smell like fresh washed cotton and flowers and — 

“Don’t even think about it.”

Mandy whirled around to see Debbie with her arms crossed and her eyebrows raised in quite possibly the most judgmental pose Mandy has ever seen on another human being.

What?” Mandy said, knowing even as she said it that she sounds defensive.

“You’re hot for my stepsister.”

Mandy splutters out a “What?!?! I—hot for—uh, huh, no! No I’m not!”

Debbie rolls her eyes. “Well, anyway, you were pretty pathetic, but don’t worry, Karen probably didn’t notice.”

Mandy feels like she’s in some weird opposite world where she and Debbie can be casually having a conversation about a crush on a girl. The Angels, as part of their no-holds-barred lifestyle, really enjoyed going out to dive bars on the road and beating up people they termed “homos.” Once, her dad had come home at 7 in the morning, sat down at the table where Mandy, Mickey, and their brother Colin had been eating breakfast, and said “Boys, if a slut ever tells you she’s a dyke, just fuck her. You’ll get her moaning like a prize pig soon enough.” Mandy had gotten up and done some dishes, hands shaking even though she wouldn’t really be sure she liked girls for a few more years. When she found out, after meeting a hot Hell’s Angels groupie who was willing to experiment with her sexuality with a teenage girl if that teenage girl’s dad was the singer for her favorite band, she just shoved it down and started sleeping with boys even more. Maybe, she decided, if she was as slutty as possible with boys, nobody would ever suspect her of liking girls. And she liked boys, she honestly did. She could ignore the liking girls part of her sexuality and still be happy. But now she was thousands of miles from Terry, and she had just seen the prettiest girl in the world, and this kid was talking about gay crushes like they were normal, and Mandy’s whole body was feeling fluttery and weird.

Debbie seemed to understand her panic. “Listen, it’s not a big deal if you like girls. To me or to most of the kids here.” She paused. “They might, you know, do douchey shit — try to get you to make out with girls in front of them, or have threesomes with you, but you’re not gonna get killed by anyone here or anything.” She smiled. “My brother Ian’s gay. He goes here too. So you aren’t the only one.”

“Listen Debbie—” Mandy swallowed, and started again. “Listen. I’m not gay.”

“Okay,” said Debbie. “Whatever. But anyway, don’t get too set on Karen. She’s been known to make out with girls when she’s drunk, so you might have a shot, except none of us are allowed to date until the older ones have.”

“How many older siblings does Karen have?” said Mandy, trying to sound like she had a casual interest instead of an urgent need to know.

Debbie smirked. “Well, there’s Fiona, then Lip, then Ian. Fiona’s in college, and she had a bunch of boyfriends in high school, and Lip is a senior. He has a girlfriend named Amanda.”

“So it’s just Ian?” asked Mandy, as Debbie started walking her towards her first period class. 

“Yeah. Only, like I said, Ian’s gay. So he doesn’t have many options.”

“Shit,” said Mandy, then quickly backtracked, “I mean, that sucks. For Karen." 

Debbie rolled her eyes. “Whatever you say, Milkovich. Whatever you say,” she said, as she walked away, leaving Mandy in front of a classroom door, feeling like her stomach was falling out of her body. 

Fuck high school.