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Derek Danforth x GN!Reader
Part 1 | Part 2 | Part 3 | Part 4 | Part 5 | More parts coming soon
Summary: As Derek gets drunk, he spots a rather attractive person he feels desperate to spend the night with. Consequently, you were tasked with helping him sober up so he wouldn't be so foolish when approaching her.
Word Count: 4.4k
Content: gender-neutral reader, angst, Mickey angst, fluff, drinking, throwing up (brief mention of the texture), Derek's mommy issues continues, reader and Derek get closer
Ao3 Link
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"Huh?" You nearly scoff at Derek's abrupt proposal.
"It's five o'clock somewhere," he reasons, beginning to sit up on the bed with an eager smirk.
"Uh, yeah, actually, it is," you huff, looking down at your wristwatch, "it's literally five here."
"Okay, great, even better," he says, immediately getting up from the mattress, "let's go."
"Wait, hold on," you interject, stopping in front of him. "There's no way you're getting blackout drunk at a time where you're supposed to be keeping up a good reputation! And, what, especially in front of those investors, who, conveniently, are also on this boat! Derek, you're going to blow your own cover!"
Derek gave your words the smallest amount of thought until he shook his head dismissively. "That's why... You can keep an eye on me."
What the hell.
"Seriously? You drinking your ass off is one thing, but leaving me out of it? That is so unfair!" You exclaim angrily. "This was your plan, and the only person being tortured in this deal so far is me! I always get the short end of the stick! Jesus Christ, Derek, have some, what, consideration? I'm bending over backwards for this bullshit, and you don't have any decency to advocate for me!"
Derek was always frustrating. Hell, you never really knew how you were still friends with him because somehow, you two just made it work. He was a shameless product of nepotism; he went from eating baby carrots to caviar off of the same silver platter ever since he was born. He was arrogant, selfish, inconsiderate, and an overall pain in the ass. He would boss everyone around him, regardless of age or role, unless, of course, they were his mother.
But he was barely his mother's son. As respectable and graceful as Jessica Danforth was, he was the complete opposite. Unlike her, he couldn't last a meeting without rudely interrupting somebody, so who's to say he could lead an entire nation? Derek was difficult, and that was that. It was like walking on eggshells trying to deal or negotiate with him, even if it was the most mundane, simple thing. Yet you were still best friends with him, yet you agreed to this overcomplicated deal to help him. Really, it was tricky to pinpoint why exactly you still dealt with his bullshit. Hell, the only thing you could seem to truthfully admit was that he wasn't so much of a bad person.
Sure, he had his whole phishing scam business. That wasn't excusable. But Derek always had his ways of showing his care for others, even if a few are unethical. He wasn't 100% malicious, nor a sociopath. The point is, even after all this, he cares about you and the people he loves. It's not an amazing quality, as it should be an inherent trait in a human being. But for Derek, it's a start.
Still, you were pissed as hell.
"Fine, fine!" He huffs, taking in your words. He should've felt bad for you, he should've felt guilty, but when it came to situations like that, he couldn't exactly read the severity or the implications of his own actions. "You can drink with me."
You sigh as Derek was still not understanding it, mostly because he had always been very dense. "No, I don't w—"
"Then what the fuck do you want?" He interjects, eyebrows furrowing. "You want to drink, you don't want to drink—"
"I want you to be responsible," you say harshly, watching his lips form quickly into a frown. "The whole reason, the whole fucking reason why we're here, why I'm here, in the first place, is because you wanted to prove to your mom that you're 'good now' and that you deserve every penny she gives you. And if you can't even follow your own plan, then this is all pointless. It's bullshit."
Finally, Derek consciously absorbs your reasoning. He was still stubborn about it, but he, for once, wasn't going to be a big asshole while knowing he was in the wrong. He hated how you were always right, and he especially hated whenever it felt impossible to argue with your logic.
"I won't drink too hard," he says in defeat, his volume lowering, "you can drink with me, no babysitting. We're on vacation, we can play it off that way. No hard drinking, no hard drugs in front of anyone, and I won't seem like that guy who took a belly shot off a stripper from weeks ago. Does that sound good?"
You didn't exactly want to scold him either. You weren't his parent, but he could be so childish at times that it's impossible to treat him like an adult. So now, with him making that compromise to accommodate to your wishes, it felt so artificial; unsatisfying when he gave in. Because all you felt like at this moment was, well... his parent.
"I'm just advising you," you exhale, sitting back down on the edge of the bed. "I'm not trying to tell you what to do, I'm not your mother. I'm just... I'm just saying, it's probably not good to go crazy tonight if you don't want to get caught by Wallace or your mother. But you know what?... Do whatever you want. I'm kind of exhausted, so I'll probably just shower and hit the sack."
Derek pursed his lips, observing your current beaten state before shrugging slightly with a sigh. "Alright. Uhh, I'll be at one of the bars, probably meet up with the rest of the guys." You simply just nodded at his words. "And Y/n... You know you're always welcome to join us. I'll pay for your tab, it's whatever."
You nod again, watching him get ready to leave the room.
Of course, there's been a lot of tension that the two of you never got to release on each other. Just always brushing it off with humor and playing it off as "playful banter." It was frustrating, though; you having to deal with Derek's recklessness, him having to deal with your responsible rationality. You were each other's anchors, which was what made your friendship worked—or at least you thought.
The problem was having to be in this role where you had to pretend to be his romantic partner. You hated the lack of authenticity. Even knowing you had to fake it, even knowing it was fake, you hated how this was a lie. But you didn't know what made you feel worse; having the public think you were dating your best friend or the fact that this kind of relationship would always be impossible that it can only ever exist as a lie.
No, that's ridiculous. You didn't see him that way, of course, you would never date him. It was just insulting to you, that's all. Dating you shouldn't be so painful to lie about. Dating you shouldn't feel so condescending. You would be a great partner, you thought. And that was definitely your problem with this entire plan. Nothing else.
***
As Derek left the cabin, leaving you to take a shower, you decided to explore the ship afterwards, just for the time being. As your footsteps would gently meet the lavish planks of the deck, you spotted a familiar figure looking out at the ocean in a reflective fashion.
"Mickey?" You ask, standing beside him after realizing who it was.
"Oh. Hey, Y/n," he smiled weakly at you, looking back at the faint horizon line where the sky met the sea.
"How are you feeling?" You inquire, considering what happened in the past between him and Derek.
"I'm fine," he shrugs, shaking his head dismissively. "Seriously, it's not a big deal."
"I know," you remark, placing your hands on the railing as you stood on the edge of the ship with him, "but... I don't know, you've been so quiet. It's just... The friend group's never been the same ever since."
Mickey ponders at your words, feeling a wave of guilt, and then exhaustion. "It's not like I, um, like him anymore," he mutters, barely looking at you. "It's just, uh... I guess I'm just... offended? Like... Would it have been that embarrassing to be seen with me, y'know? I mean, I know I'm not perfect and, hell, invest too much in crypto, but... it's not like he's any better than me. But he constantly acts like it, which is fucking frustrating."
You frown as you listen to his perspective, sighing to yourself. You couldn't disagree, he was a hundred percent right. "Derek's a dick," you huff, "honestly, it's surprising how all of us, at one point, are able to stand it. But... You know him. He's afraid of intimacy. Real intimacy. He's too afraid of getting too close to someone, too afraid of disappointing anyone. He thinks it's better to leave first so that he doesn't get hurt."
"So then I should get hurt?" Mickey scoffs, looking at you now.
"No, it's just... I'm not excusing his actions. What he did was completely idiotic. All I'm saying is... he's a moron. Anyone would be lucky to have you. Derek's just... not exactly the standard for dating or the arbiter of who's a good partner, so... you're not as unworthy as he might've made you feel."
He pursed his lips, face contorting in contemplation. "It's just... I feel so used. I know, I knew it was a fling and there was nothing else to it, but... One of the things he told me was that we couldn't... be anything more because he didn't want to be seen dating a friend of his, or someone who doesn't come from a rich family, and..."
That was your exact concern.
"He's only doing this because his money's at risk. That's all," you reply softly, "there is no other motivation bigger than losing his money for him to fake date one of his friends, let alone me. It has nothing to do with you. I promise you that."
Mickey shrugs, disregarding your words. Not maliciously, just... unconsciously. Then you realized it was much more of an internal struggle. He needed direct closure from Derek himself. "I'm gonna go get a drink," he nods at you kindly before walking away, "thanks for this..."
As you watched him leave, you frowned to yourself, feeling the exhaustion of today's events finally catch up with you. Hell, you needed a drink too.
Motivated to search for one, you turned your body around, facing away from the view of the ocean. Suddenly, your eyes trailed to the empty lounge chairs on the deck with their corresponding tables. A box of Capri-Sun was just sitting there, unattended.
Huh. Change of plans.
***
The alcohol burned his throat as Derek took a swift, smooth swig, hearing the laughter and shouts of his friends around him. This was probably his fifth damn shot ever since the group occupied a colorful bar in the cruise ship. Soft music played in the background as they all sat in a cushioned booth.
"I can't believe Y/n isn't here," Rachel huffed in disappointment, looking around the space as if you would pop out of thin air.
"Yeah, well they're a fuckin' lame-o," Derek slurs, swishing his empty shot glass around, "why are they so serious? They've never been so uptight before. It's so annoying."
"Maybe because you put them in a position where they have to be your partner?" Trevor raises an eyebrow, sneering playfully. "No offense, dude, but I feel like anyone would feel humiliated if they had to date you. Again, no offense."
Derek shot him a menacing glare while everyone else laughed at him.
"I stand by that," Connor cackles, elbowing his friend, "being romantically involved with the country's nepo-brat himself? Says a lot about your self-respect."
"Shut the fuck up." The said nepo-brat retorts as he feels his head throbbing. He wasn't actually upset, however, despite his enormous ego. Even as his friends weren't so far from the truth, he could easily handle their targeted jokes. Unlike a large sum of people, they surprisingly didn't befriend him for his money. After all, they had several things in common: being rich, being educated, and being grade-A assholes.
"Hey, Danforth," Trevor pipes, shoving him obnoxiously, "hot chick, three o'clock."
Derek looks in the direction he was told, only to see a tall, gorgeous woman around his age, sitting on a barstool while mingling with her friends. Of course he was never new to her level of beauty, as he's hooked up with all types of people in the past. So no, her looks weren't the reason why he felt so desperate now. Truthfully, it's been a long time since he's gotten some. Ever since this whole fake dating arrangement, Derek had never gotten the time or chance to get into bed with someone enticing, or just anyone at all. He was always a fan of pleasure, a big fan of one-night stands. And right now, he was craving one.
"Fuck," he groans, strongly motivated to push through the drunken migraine he was experiencing. "I gotta... go talk to her..."
"No, dude," Trevor huffs in amusement, trying not to burst out into laughter, "you're way too drunk, you'll scare her away."
Derek frowns, unappreciative of his friend's deliberation. "I swear to fuckin' god, Trev, if I don't bang at least one goddamn person on this boat—"
"Relax," he chuckles, massaging Derek's left shoulder, "I'm just saying, you should sober up first. Not too sober, obviously, but you need to be well aware enough to make smart choices. Like, I know you'd fuck up the whole you and Y/n thing and someone's gonna find out." Derek nods as he listens to half of the things he heard, eyelids growing heavy. "Go back to your room, Y/n can sober you up, and when you're ready, you can come back and screw this girl."
Derek's thoughts were hazy and ran slowly in his brain like traffic. He couldn't focus on any of the steps instructed to him, nor did he feel inclined to comply.
"Hey, you know something?" Rachel chimes in, "there's this one thing you always do whenever you're way too drunk to function. It's almost, like, a signal for when you should stop drinking for the night."
"Oh, yeah!" The rest of the group exclaimed in a discordant manner, all laughing at the inside joke Derek wasn't yet aware of.
"What?" He furrowed his eyebrows curiously. "What do you mean, what do I do?"
"Basically," Connor chuckles, "we always know you're far too gone whenever you propose doing a flip. You say that every fucking time you're too drunk. Not when you're buzzed, not when you're tipsy, but every single time you're absolutely hammered. I swear, every time you're, like, 'watch me do a flip' or some stupid shit like that."
"No way," Derek grumbles in refusal, not recalling any memory of him saying those things, "I don't do that." To be fair, however, he wouldn't even remember anything from the times he was too drunk. Therefore, he couldn't even be a credible source for his own experiences.
"Uh, yeah, you do! Every time!" Rachel cackles with a wide grin. "One time, we didn't stop you because you wanted to do a skateboard trick, and you absolutely ate cement, man. We even got that on video!"
Derek groans in embarrassment, feeling his migraine grow. "Whatever. One more drink," he grumbles before a knowing smirk appears on his lips. Everyone around him scowled, watching him down more liquor, even if he was far too deep in intoxication.
"Hold on, one more," he giggles shamelessly, as he quickly finished the previous drink.
***
"Derek?" You huff in surprise as you hear the door swing open, seeing your friend stumble back into the suite.
"H—" before he could even say one word, he rushed to the bathroom to throw up in the toilet. As he fell on his knees, his hands gripped the poor, porcelain seat of the toilet. You followed him immediately, placing your hand on his back in deep concern.
"What the hell?" You gasp, "dude, how much did you drink?"
Derek coughed out the last bits of vomit, staring straight at the toilet bowl and the floating chunks that left his stomach, furrowing his eyebrows. "Where does flushed shit go on a boat?" He mumbles distractedly, failing to answer you. "Does this go straight into the ocean? That's so messed up..."
You roll your eyes anyway, having been accustomed to his drunken mannerisms. This actually wasn't the first time you dealt with him like this, which probably made you harsher than anyone would've been in this scenario. "Why would you care about what's messed up or not? You literally run one of the most immoral businesses in the world."
"Yeah, well, doesn't look like you're doing anything to stop me," he scoffs bitterly, looking up at you in the eyes, "having said that, you're just as bad as me."
You hated whenever he brought this up to refute you. How you never bothered turning him in, never bothered telling anybody. But was that not your moral obligation as his best friend? Were you supposed to get him caught or keep his criminal life private? Why did you seem to prioritize him over the thousands of vulnerable people in this world?
"I'm fucking with you," he smirks humorously, while you knew damn well he wasn't kidding. "I need to... sober up. There's this... chick at the bar I wanna hook up with and I can't risk anything, so... just need to be more conscious or whatever bullshit Trevor said. Can you help me?"
Immediately, you disapproved of it. "That's a terrible idea," you retort. "If anyone finds out about this, you'd be deemed a cheater. I don't care who you sleep with, but the purpose of this trip—"
"I'll make sure she keeps it a secret. Pay her, even," he says, his squinted eyes pathetically trying to meet yours, "Come on. Help me."
Why did you even bother?
"Fine," you sigh, standing up from your knees to flush the toilet.
The two of you sat quietly on the edge of the bed as you handed Derek some water. He gulped a substantial amount after muttering a thank you.
"You know you can't truly 'sober up' that fast, right?" You scoff. "You'd have better luck sleeping it off."
"But I have her right where I want her. It's a filthy one-night stand, not a perfect meet cute," he grumbles before taking a second glance at you. A foil juice pouch was in your hands as you ripped off the attached straw. "What is that? Holy shit, is that a Capri-Sun?"
You nod, poking the pouch's hole with the thin yellow straw. "Yeah."
"Where did you get it?" He asked with a sudden deep interest.
"I just... found some lying on a table on the decks, it probably belonged to some kid," you shrug casually.
"You stole it?" He huffs in shock, not expecting you, of all people, to do such a thing.
"Derek, think about the kinds of people who can afford this cruise, okay? Upper class families. I'm sure whoever it is, they'd be okay with a few missing Capri-Suns," you scoff. "I can promise you this, dude, it's not as bad as stealing money from old people." Clearly, you couldn't help but constantly bring it up. You had always felt bitter about it the moment he told you of it.
Derek pouts before groaning, sinking down towards you to lay his head on your lap. You were only slightly taken aback, as this was a common habit of a drunk Derek. But it was always surprising to you nonetheless, since you never really knew when he was going to do that. "It's not like... I'm evil, you know?" He mumbles bashfully.
You raise an eyebrow at his quiet words, letting him continue.
"Of course it's fucking unconventional and immoral and whatever. But the thing is... I'll never make the amount of money my dad did when he was still alive. And you're telling me I have to follow in his footsteps? That's ridiculous, for me, at least," he huffs. "Especially for me, actually."
You didn't know what compelled you to do so, but your hand landed on his head, feeling his soft curls between your fingers until you could feel his scalp. You were nearly petting him. And you hated it because ultimately, it confirmed your sympathy for him. You genuinely almost felt sorry for him. So what else were you supposed to do anyways?
Derek felt his heart tighten at your touch. It was all too familiar. Too much like his mother's. But he didn't want to think about it like that, not when it was you. "Everyone used to expect so much of me, even before Dad died. Until they learned that all I could do is disappoint. Now everyone expects the very least of me, which, fair enough.
"Danforth Enterprises has been slow, especially ever since I took the position. And I'm supposed... I owe something to my mother. I owe everything to her. And if all that money could... get her to be president, get her to think I'm a successful CEO, then... that's just... That's why I do it. I just... was far too gone. I'm in too deep now."
Derek felt a sting every time you stroked his head. It was horrible, it was as if he was back in his mother's grasp, when everything was much simpler, when he wasn't seen as such a failure. When a damn drawing of the private helicopter in crayon was the best thing he ever did in her eyes. When did he become such a disappointment now?
"It's shitty," you sigh, your own voice grounding him. It was you. This was your hands, your touch, not his mother's. The same voice that belonged to the smile that greeted him in his freshman year at MIT. You. "That doesn't excuse it, and I'm sure you know that. But... You're being too hard on yourself, Derek. I'm sure your mom would've appreciated it if you genuinely worked hard and show that you earned that position. The extra flashy money obviously never worked."
He hated being scolded. Being told what to do. But somehow, your words were a comfort to him instead. Maybe he was this vulnerable because he was intoxicated, but that was rarely ever the case.
The one thing he knew right now, though, was that it was your hands, your fingers, your touch, your voice that embraced. Not his mother's. And for that reason, he loved it.
"Can I have some of your Capri-Sun?" He asks coyly.
"You shouldn't have any sugary drinks when you just threw up," you advise.
"You're just gatekeeping it," he grumbles, shutting his eyes.
A soft chuckle leaves your lips as you continue to scratch his scalp. Derek felt his heart rush at the sound.
"You have a nice laugh," he mutters.
You paused your hand movements on his head, stunned by his words. "What?"
"I like your laugh," he confesses quietly, opening his eyes and fidgeting with his fingers. "It's nice." Then, he nudged your body with his head as a plea to resume your touches.
You continued playing with his hair curiously. He's never acted like this around you. Ever. What changed?
"Th—"
"And I mean it," he adds, closing his eyes once again in contentment, "you're great. I'm sorry for getting you caught up in all of this. It was never fair to you."
You sigh softly at Derek's admission, feeling the curly strands of hair beneath your fingertips. "Thank you," you mutter appreciatively.
"I know I said I'd make it up to you with Fiji and money, but... that's probably not enough. Maybe I'll be a 'yes-man' for a week. I dunno. Something like that," he reckons.
You felt so warm right now. You weren't sure what it was. Either a metaphorical would-be-disaster of a feeling or the fact that Derek's head was resting on your lap, giving off heat. And while you could admit that you enjoyed the feeling, you realized you might've distracted him from his initial goal.
"Come on, buddy," you sigh, trying to prop him back up, removing his head from your lap, "I think by the time you walk back to the bar, you'd be all ready for her."
"Oh, right. Oh yeah," Derek huffs as he also remembers the whole point of coming back to the room so early, "yeah. She's, uh, she's so not ready for this." He chuckles weakly, gesturing towards himself.
You pat his shoulder in a friendly manner, establishing the extent of your relationship. Friendship, rather. "Give 'em hell," you smile softly, helping him get up before he walked by himself towards the door.
Once the door closed behind him, Derek stood in the hallway, feeling unsure of himself. He felt lost, and it wasn't just because of the alcohol. He began to retrace his steps, vaguely remembering the face of the woman at the bar. Yes, she was pretty, but... for some reason, he just didn't want to go through with it. Which was insanity, because Derek never passed the chance to screw an attractive person. It all just felt so different, all of a sudden. Like there was a consequence and that it mattered. Like it just wasn't right to do.
He wanted to go back into the room with you.
He didn't care about the woman at the bar.
He really didn't want to admit it, really, but all he wanted was to be held by you once more. Just for a little longer.
And there was only one excuse that could help him get away with it.
Your eyes shot up as you hear the door burst open once again, seeing Derek stumble more messily than before.
"Hey, wait. Before I go... watch me do a flip!" He smiles widely, purposefully slurring his words.
In your perspective, Derek definitely wasn't sobered up enough to meet with that girl he was talking about. Surely, the flip nonsense would signify he was way too drunk to function. It was something he's always done that you and your friends noticed. Finally, you concluded that he could barely sober up in time before the night ended, having to stay with him like this, which was exactly what he wanted you to think.
Rolling your eyes with a slight grin, you scoff. "Come here," you groan, watching him come back to you. You handed him a Capri-Sun, finally, as you two sipped the juice in contented silence. And soon enough, his head was back in your lap as your hands were back in his hair.
