Warnings: Underage drinking, drug use, sensuality, sexual implications, and language
A/N: Y/O/B/F/N= your other best friend’s name
“Why didn’t I skip class today?” Mandy groaned, throwing her head back.
“Because if you got caught skipping again, you would get suspended…again,” Lip muttered behind her.
They were sitting in their eighth period British Lit class while Mr. O’Neil talked about some dead poet. Lip was only paying half attention since he already knew most of the information and he got good grades without even trying. He had a few more important things on his mind like Fiona and his other siblings and the trouble he and Ian could get into over the weekend. However, the other kids in the class could hardly afford zoning out in the way he did.
“…and that is how Edgar Allen Poe invented the modern detective story,” Mr. O’Neil concluded with a small smile under his wiry gray mustache. “Now, before you leave, I have to return your midterm essays.”
“What’s the point? I know I failed,” Mandy muttered.
“You never know. You could’ve gotten a D this time.”
Lip smirked as Mandy turned around to slap his arm. It stung a little, but Lip laughed it off.
“We can’t all be weird geniuses like you.”
“Most of you did not seem to grasp the concept I was looking for, which is confusing since all I requested was for you to dissect and analyze a piece of literature we previously discussed in class,” Mr. O’Neil said as he began handing back papers.
A lot of the kids rolled their eyes, laughed, or groaned when they received their papers. It took a minute for Mr. O’Neil to get to Mandy and Lip.
“I expect more from you, Miss Milkovich,” Mr. O’Neil said.
“Have you met my brothers?” Mandy retorted.
Mr. O’Neil cast a distaste look in her direction, but recovered a little as he handed Lip his paper. “Very good work, Mr. Gallagher.”
“Thank you, Mr. O’Neil,” Lip said.
Scrawled on top of his paper was a 90 along with the comment “Good work, Mr. Gallagher. Your input was interesting but the dissections were a bit off.”
“Not bad, Gallagher,” Mandy muttered.
Lip couldn’t help but feel a little proud of himself. He was always the smartest person in the room, even though the room primarily consisted of idiots. It was nice to be reminded of it.
“Miss Y/L/N, I was quite impressed with your work. I have never read such original or thoughtful input on Emily Dickinson.”
The girl had a small, wan smile on her lips as she accepted her paper. “Thanks, Mr. O’Neil.”
“In fact, you scored the highest on this assignment.”
Y/N smiled shyly yet again and muttered a polite “thanks” to the teacher as she placed her essay neatly in her English folder.
“Looks like Little Miss Perfect beat you out,” Mandy teased in a whisper.
“I’ll let her have it, this is probably the only pleasure she gets out of life besides reading and studying all the time,” Lip muttered.
Y/N Y/L/N had to be the most innocent girl Lip had ever encountered and she was also his biggest competition when it came to academic standing. She was smart as a whip, but she didn’t flaunt it like Lip did sometimes. In fact, she mostly kept to herself, save for the two girls Lip saw her hanging around. Y/N was every parent’s wet dream: quiet, polite, kind, and a bit of an over achiever. She was the class president, captain of the debate team, and captain of the girl’s tennis team. In fact, the only trouble she probably got in was for jaywalking. Lip didn’t really have anything against her but he also didn’t really like competition.
Finally, Mr. O’Neill released them, and Mandy and Lip were the first two out of the classroom.
“Just admit it, Lip, you don’t like that Goody Two Shoes beat you out for the highest grade,” Mandy said.
“It’s just a stupid essay, Mandy, besides, getting good grades is probably the only way Y/N could experience an orgasm,” Lip said.
Mandy burst out laughing and Lip smirked deeply. “That is true, I don’t think Y/N would know what to do with a dick if she ever saw one.” As Mandy and Lip laughed, they were interrupted by someone running into Lip.
“Hey, watch where the f–ck you’re going,” he snapped.
“Oh, sorry!” Y/N squeaked.
Lip instantly regretted his words when he saw how Y/N clutched her book to her chest. “It’s fine, forget about it.” “Hey, Y/N,” Mandy said.
“Hey, Mandy.” Y/N readjusted the strap of her messenger bag. “Have any fun plans for this weekend?”
“I might go to a party or two. You?”
“I am keeping my options open.”
“Y/N!” Y/B/F/N yelled from across the hallway.
Y/N sighed a little. “I have to go, sorry about running into you like that, Lip.”
“Don’t worry about it.”
Y/N hurried off to meet her friend on the other end of the hallway and they immediately began giggling together. Y/B/F/N said something to Y/N that made her eyes widen and take a quick glance at Lip. When she saw that he was looking at her, she quickly turned back around to her friend, who began snickering.
“Hello, earth to Lip?” Ian asked.
“What?” He turned to face Ian and Mandy.
“I was asking if we were still going to Rose Martin’s party tonight,” Ian said.
“Why wouldn’t we be?”
“Because it’s in Old Town and we’re south side trash.”
“Hey, we’re only trash if we think we’re trash, so stop thinking we’re trash,” Lip said.
“Fine. Now tell me, what had you so distracted that you couldn’t answer me?” Ian asked.
Mandy smirked. “It was because of her wasn’t it?”
“Who?” Ian asked.
“Shut up, Mandy,” Lip said.
“Y/N, Lip’s got a thing for her,” Mandy said.
“Y/N Y/L/N? The same girl who cried when Eddie Carver kicked a baby rabbit over the school fence?” Ian asked.
“That was third grade,” Lip said. “And I don’t like her like that.” “Why not? Because she’s too good for you?” Ian teased.
“No, because she’s too f-cking innocent. It would be like being with a little kid all the time,” Lip muttered.
“I would believe you if you hadn’t been eye-f-cking her a second ago.”
Lip didn’t respond, and he didn’t really know why he had gotten so defensive when Ian and Mandy began suggesting that he liked Y/N. He barely spoke to her except in passing and there was no way she would go for a Gallagher of all people. Somehow, he still found himself attracted to her innocent, shy nature. He would ruin her and she didn’t deserve that.
Late that night, the party was in full swing at Rose Martin’s penthouse in Old Town, Chicago. Her father had won the lottery two months ago, so the penthouse was filled with gaudy art, strange mini statues that were considered art, and stainless, techy everything. Waka Flocka’s “It’s A Party” was blasting through the speakers as teenagers grinded to the beat throughout the penthouse. In the kitchen, a group of people were playing drinking games; the bathroom was dedicated to cocaine; the bedrooms were used for coitus; and the balcony was for the cigarette and pot smokers. Lip, Ian, and Mandy were in the living room in the middle of the chaos, dancing as they drank. Lip was near the threshold of being drunk, but was still in the place where the colorful lights didn’t transfix him and he still had control of himself.
“This is the best night ever!” Mandy shouted over the music.
Ian and Lip shouted in response before they toasted her words and downed the vodka in their cups. It went down smooth since Rose could afford not to scrimp on the alcohol anymore.
“I love Rose Martin!” Ian exclaimed.
“You can’t, you don’t swing that way!” Lip shouted back.
Lip and Mandy burst out laughing. In the midst of the madness, Mandy ended up grinding with some guy and Ian disappeared. Lip ended up wandering out of the living room and went outside to light up a cigarette. The sky was completely ink black with a few stars scattered in the mix. A few people were smoking pot or cigarettes around the balcony. In the corner was a group of girls wearing short dresses and skirts, giggling. One of them looked extremely familiar to Lip but he couldn’t put his finger on it. She flipped her y/hc ponytail and burst out laughing at something before turning around. Lip nearly dropped his cigarette.
“Y/N?” he whispered.
She was wearing an oversized blue button down shirt that managed to accentuate her curves with a pair of black over the knee boots. Her hair was pulled in a ponytail with a few strands falling around her face, which was made up in a tasteful fashion with gold eyeshadow bringing out her y/e/c eyes and blush to compliment her skin tone. She was holding a plastic cup filled with white wine and her friends had sneaky smiles on their faces when they saw Lip.
“Lip!” Y/N stumbled over to him, managing not to spill a drop of her wine. “It’s so good to see you.”
“What are you doing here?” Lip asked.
“Drinking.” Y/N took a long swig of her drink to prove her point.
“I can see that, it’s just, this isn’t really your scene.”
“I guess you don’t know me as well as you think you do.” She managed to smolder at him which managed to both amuse and arose Lip at the same time.
“How many of those have you had?” Lip asked.
“Don’t worry about it, Dad, I can handle my alcohol, see?” Y/N downed the rest of her wine and smiled.
“Maybe you should go back to your friends.”
“I’m sick of them, I want to talk to you.” Y/N leaned more of her weight into Lip and he paused to grab her.
He kept his lit cigarette between his lips as he pulled her to stand upright. “Fine, let’s talk.”
“Can I try one of those?”
“Why would you want to smoke?” Lip asked.
“Because I can.”
Lip looked at her skeptically before handing her cigarette and lighting it for her. Of course, Y/N almost immediately began coughing, making everyone turn to look at her and Lip. Lip shook his head as he patted her back.
“You have to inhale deeper before you exhale, like this.” Lip showed her and Y/N nodded before following his lead. “See, it’s easy.”
“Thanks,” Y/N said.
“Geez, I feel like I’m corrupting you.”
“You’re not. I’ve done a lot more than you think I have.”
“What does that mean?”
Unfortunately, Lip was interrupted by the strains of “Hips Don’t Lie” coming from inside. Y/N squealed. “I love this song!”
She tossed her cigarette down and ground it out with her toe before hurrying inside.
“Y/N.” Lip got rid of his cigarette as well and followed Y/N’s lead.
He almost immediately lost her but quickly spotted her dancing with Ian. They had created some sort of salsa two-step that mostly consisted of Ian twirling Y/N around and dipping her. Though Lip trusted Ian, he couldn’t help but feel protective over Y/N. It was strange how worrying about her sobered him up.
“You’re being ridiculous; you barely know her,” he hissed to himself.
He decided he needed another drink and headed into the kitchen. That’s where he found Mandy, mixing drinks at the kitchen counter while another group of people played flip cup.
“Hey, stranger,” Mandy said as she poured a drink into a glass.
“What made you hide out in here?” “Tyler Sanders’ hands kept wandering to places I did not want them to. I decided to see how good of a bartender I am.” Mandy handed him the glass she just poured.
“Thanks.” He took a sip. “Not bad, what is it?”
“Of course. Did you know that Y/N was coming?”
“No, but I saw Y/O/B/F/N leave the bathroom wiping her nose and figured Y/N had to be around somewhere. She is full of surprises.”
“Yeah,” Lip muttered.
“Do I need to make you another drink?”
“That sour look on your face wouldn’t have anything to do with Y/N being into the party scene, right?”
“Not really, it’s just weird seeing her drunk.”
“I like it, it makes her more relatable. She’s not better than either of us.”
“Of course she’s not. She goes to a Chicago public school.”
“True, but maybe you’re so weirded out by it because you liked the idea of her being super innocent and you don’t like that you can’t be her first, well, whatever.”
He hated how right Mandy was sometimes. While it was kind of cool to see Y/N let lose, Lip kind of liked the idea of making her do something bad just for him. He had no idea when those feelings started but seeing her act so drunk was bringing them out.
After a couple more drinks, he and Mandy made their way back into the living room, where Y/N and Ian were the center of attention. It made sense since the openly gay Gallagher was grinding with the supposed sweetheart of the south side.
“Y/N’s got moves,” Mandy said.
“Uh huh,” Lip said, trying to ignore the tinges of jealousy creeping up on him.
However, everything came to a head when Y/N pulled Ian close and they began making out, causing everyone to scream and yell. That was the last straw. Lip quickly broke them up, much to the crowd’s chagrin.
“What the hell, Lip?” Ian demanded.
“Ian, you don’t know what you’re doing, you’re drunk and you have a boyfriend,” Lip hissed.
“Not really, besides, Y/N’s a good kisser. Were you jealous?” Ian shot back.
“Jealous? Why would you be jealous?” Y/N slurred. Then she grinned. “You wanna dance with me, Lip?”
She wrapped her arms around Lip’s neck and leaned into him. Lip’s arms immediately wrapped around her waist out of instinct but he didn’t start dancing. Mandy and Ian had begun dancing together somewhere else in the room.
“Y/N, you’re drunk.”
“I wanna dance.” She turned around in Lip’s arms and began grinding against him, leaning her head against his chest.
Lip gulped before hesitantly grinding with her, holding her hips and keeping her pressed against him. He didn’t know what got into him but he began kissing down the side of her neck. Then, he turned her to face him and grabbed her face in his hands and really looked at her. Her eyes were completely dilated but she was so beautiful.
“I can’t do this.”
“Do what? Dance with me?” Y/N teased.
“Not just that, it’s, you’re too perfect. You deserve better than this, better than me.”
Lip moved to pull away from Y/N, but she grabbed him. Her eyes held a deep sincerity in them, albeit they were extremely dilated.
“You’re perfect,” she said with a large smile.
“Yes, but I know that you’re funny, really smart, and loyal, a little impulsive, and a bit self-destructive. And you’re daring and really, really, really hot,” Y/N said.
“You really think all that about me?”
Y/N nodded. “Ever since second grade, but I thought I wasn’t cool enough for you, but I do go out sometimes and I have made many questionable decisions.”
Lip had a lot of questions, a majority of which had to do with what questionable decisions Y/N had made. But, all he could think about was how Y/N thought she wasn’t good enough for him.
“You’re cool in your own way.”
“Now that’s a load of bullsh-t.” Y/N started laughing, a sound that made Lip smile.
He cupped her face in his hands again and slowly, she stopped laughing. Lip stayed quiet and leaned towards her slowly. Y/N closed her eyes, awaiting to be kissed only to be surprised when Lip kissed her on her forehead.
“You missed,” Y/N said.
“No. I want you to remember the first time I kiss you and you’re way too sh-tfaced to do that right now. If you still feel the same way about me when you’re sober, we can pick up where we left off.”
“But I want you now. I promise I won’t regret it.”
Lip didn’t listen to any of her protests as the night went on. So, they continued dancing, earning winks and rude gestures from Ian and Mandy. When the party was over, Lip took Y/N home to make sure she was safe.
“But who’s gonna walk you home?” Y/N asked as Lip helped her walk up the steps.
“Why do you get to walk yourself home and not me?”
“For one thing, I wouldn’t fall if you let go of my shoulders,” Lip said.
Y/N huffed and leaned against her front door. Lip fished her keys out of her purse and unlocked the door for her.
“All right, now be quiet. The last thing we need is your parents coming after me.”
Y/N nodded and wrapped her arms around Lip’s neck, giggling quietly. Before Lip could stop her, she pressed a sloppy kiss to his cheek before pulling away. “Good night, Lip.”
She slipped into her house and Lip closed the door behind her.
All he could do now was pray that she felt the same way about him in the morning.