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How to Mostly Fail at Wooing Your Grumpy Next Door Werewolf: a comprehensive guide by Stiles Stilinski

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It starts like this.

Stiles creates a Howlr account because he’s watching werewolf rights activist Laura Hale verbally smackdown some middle aged republican that probably snorts pure gold during bathroom breaks. He might also be a little high at the time.

And of course because his high brain makes wonderful decisions, he decides that the best thing to do is obviously make a Howlr account and strike up conversation with a friendly werewolf about, you know, werewolf rights and shit.

Yeah, not his brightest idea he knows.

But anyways, he’s making his account, selecting through preferences and taking a random selfie as his profile pic and then waiting for the app to get him his matches while he watches Laura lay down the truth.

There’s a good handful of them and Stiles entertains himself by looking at the profile pictures taken from high angles and low angle and wow that is a nice looking dick, but not why Stiles is here.

He sorts through them lazily, peering at the TV and bobbing his head along with what queen of werewolves is saying because right, right! She’s just so eloquent with, like, words and that’s just- yes.

She’s doing so much good for werewolves everywhere and Stiles really appreciates it because look Scotty is a werewolf and the fact that his chances of finding work are cringe-worthy fewer than Stiles’ is just a big no-no because his bro needs happiness and, like, money, to woo whatever flower smelling girl he is changing at the moment.

Stiles peers down at the next profile sees a picture of a man glaring at the camera, ears red and big frames slipping off the bridge of his nose.

Derek ‘bunbuns’ Hale. 25. College student. Likes to take long walks on the beach, shirtless and on a horse and to be a buzzkill that should just get laid.

Even high Stiles can tell he wasn’t the one who picked that profile. But because he is high he thinks perfect and starts up a chat.

It’s a pretty simple text. Just a little conversation started.

»»do u wnna tlk bout gold sniffers makig a bill to ablosih mized werewulf and humaas scholz??????? also ur glasse r droppin plz fix em its distracitng

He doesn’t get an answer, at least not immediately and it’s not like he actually expected one.

The kind of stars that had to align for Derek Hale to be anywhere near his phone when he sent that are astronomical.

Stiles looks back up to where Laura is looking beautiful and so unimpressed at the stuttering man in front of her that if Stiles could jump through the screen and highfive her perfectly manicured hand he would.

He continues watching the wonder that is Laura Hale and by the end of it he’s forgotten all about the text he sent Derek Hale.


“And we’re moving in with Isaac and his adoptive brother why?”

“Support?” Scott asks, throwing clothes in his suitcase, “The rent will be cheaper. Don’t you want cheap rent? Also Isaac says Derek can cook.”

Stiles plops down on the bean bag in a corner of Scott’s room.

“And he’s okay with two other random kids moving in alongside Isaac because?”

Scott sighs, “Can’t you just- not question a good thing that’s happening?”

Stiles raises his eyebrows, “No. Are you insane? Good things don’t happen to people like me, Scott.”

“Don’t say that. You deserve nice things.”

“I literally keyed someone’s car yesterday. I’m not a nice person.”

“Weren’t they harassing the waitress at the diner?”

“That’s beside the point,” he huffs, “The point is, we’re moving to an apartment because Isaac found an adoptive werewolf family and somehow they’re kosher with us tagging along? Like, seriously? There must be a catch.”

Scott drops his eyes and does the guilt shuffle. The one that tells Stiles he’s hiding something because Scott is both a terrible liar and a terrible shuffler.

“So, they might have heard I don’t really have a pack and offered me a place in theirs?”

“And you accepted? Scott!”

Scott shrugs a little, “It’s just to see how it goes. I mean, it could be nice. Having other ‘wolves around.”

Stiles presses his lips together but it’s not like he can do anything against the slow hopeful look Scott is giving him and the big sad puppy eyes.

“Fine,” he huffs, “if this goes sideways I will let them eat you, though.”


The apartment isn’t an apartment. It’s a house.

It has stories and a porch and nicely trimmed lawn.

Stiles can just see a backyard behind it.

Stiles can also see a very surly man standing at the doorway, with his arms crossed and looking like someone shoved an entire stop light up his butt, like, wow he does not look comfortable at all.

He adjusts his glasses, picking them up by the side and slowly bringing them up to the top of his nose and kind of huffs.

“You’re Isaac’s friends, right?”


“Yes. Hi, I’m Scott!”

Scott bounds forward, dimples in full effect with one hand outstretched. Derek glares down at it for a couple of solid seconds before shaking it.

“I’ll show you the house,” he says, looks over Scott’s shoulder to Stiles, “don’t break anything,” he adds almost as an after-thought.

Stiles outrageously splutters after him into the house, tripping on his suitcase because how dare.


The thing is, he might’ve completely forgotten about the text he’s sent a couple of weeks back.

It’s only when they’re having dinner and him and Derek are having a conversation (arguing, that’s what they’re doing let’s be real here) that he remembers. And that only happens because Derek has his ears red, cheeks a little puffed up with how annoyed he is and glasses slipping down his nose.

“Fix your glasses, they’re goddamn distracting,” he huffs, because really. It makes him look like an angry librarian. It’s terrible because then, for whatever reason, Stiles starts thinking about library sex and wow okay he has no idea where that came from.

Derek drops his mouth open probably to say something but then snaps it close quickly, frowning adorably up at Stiles.

He gently shoves his glasses up his nose and glares down at his food (that he cooked, did Stiles mention that because that is worth mentioning; it’s fucking delicious) and huffs at him, “You’re intolerable.”

Derek then proceeds to shovel food in his mouth and ignore him for the rest of the meal.

Stiles is confused for the rest of the night until his phone dings with a notification from Howlr and then he thinks oh! okay. That’s what that was all about.

Stiles can’t really remember what he sent on that message, so he opens up the chat and reads over it and then he promptly face plants on the bed and groans as loudly as he can.

Figures, just figures that one of the hottest, broodiest, cutest guys he’s ever met is one of his matches on Howlr and he’s already rejected him.

But oh, oh no. Stiles Stilinski will not be easily defeated!

He will woo the pants out of Derek Hale because he’s known the guy for all of five hours and if he’s learned anything at all is that he’s helpful and rough around the edges and bites his lip with his dumb bunny teeth when he really doesn’t want to laugh and his stupidass frames keep slipping down his nose and he’s worth fighting for.

Stiles makes a conscious decision to pursue him. He makes a game plan. He’s so serious that if he had his whiteboard here he’d be making an actual plan. Which would probably be a little creepy.

He bolts upright, thrumming with nervous energy to act to go do it right now, right this second.

He kind of feels like epic Disney music should be playing in the background.

Stiles glances at the clock, sees it’s almost two in the morning and falls back down on his bed.

Maybe tomorrow. Yes, tomorrow he’ll start his grand journey to woo the pants off Derek Hale. Hopefully literally.

For now he settles for laying back down and listening to the soundtrack of Mulan.

(And maybe if he changes all the pronouns and gender identifying words in ‘A Girl Worth Fighting For’ to psyche himself up, that’s his own business, thankyouverymuch.)


Okay, so maybe Stiles Stilinski will not be as, um, frontal with his plan as one might think.

He was going to, but then he came downstairs and Derek had to be cooking in a soft looking tee and his boxers and Stiles is just- too stunned for words.

All and every word flew right out of his mind (probably towards his dick, but that’s beside the point).

He whirls around and stomps his way to the bathroom because no okay. It’s too early in the morning for that kind of gorgeous.


They’re arguing again.

Well, Scott has taken to call it banter. Isaac has taken to call it foreplay but Isaac knows nothing about nothing, so. There.

Anyways, they’re arguing again because Derek the absolute dork is getting all uptight about his nerdy ass books.

It’s European literature. No, it’s Portuguese literature. A book thick enough to cause serious damage if used as a weapon, with tiny print, about a family and an accidentally incestuous love story.

Derek likes it. Derek, because he’s a major dork, gets this almost reverent look every time he picks it up (he does it with all the classics, all books really and it’s so cute Stiles might do something drastic like kiss him).

“It’s literature, Stiles. It’s a critique on society and the frivo-“

Regardless of what it’s about. It’s European literature, Derek. There’s an entire chapter detailing a house. A house. And those are big chapters.”

Derek glares his most suspicious glare.

“How do you know that.”

So, maybe Stiles has read it. What? It’s witty, it’s actually kind of fun and skimming is your friend.

“That’s completely beside the point.”

Derek squints, tilts his head a little.

“You’ve read it,” he accuses.


His lip curls up, “You liked it.”

“I don’t even kno-“

“Which means, you’re picking a fight with me just to be an asshole.”

Yeah, that’s exactly what he’s doing, but it’s not like Derek needs to know that. Also the fucker is reading that book in original Portuguese and Stiles might be a little jealous. Maybe a little turned on.

What? Don’t you want someone to whisper sweet nothings in your ear in a different language. Because he does.

Stiles picks up his phone and okay it’s a cowardly move, he knows that okay. But here’s the thing.

This morning Derek was doing push-ups shirtless on the backyard which in and on itself had been pretty fantastic. But then this cat had wandered in and just sat staring at Derek and you know what he had done?

He had sat down on the soft symmetrically cut grass (that he probably cuts himself in the summer, shirtless and in low cut jeans because that’s the kind of asshole he is) and stared down the cat until the animal had just padded over and allowed Derek to pet it.

Just like that.

It was so cute Stiles wanted to punch something. Probably Derek’s face. Softly. With his lips.

Yeah, that would teach him.

Stiles opens up Howlr and taps a quick message.

»»u still need to fix ur glasses, dork

“Do you have Howlr?” Stiles asks and Derek frowns, which fair. He might’ve just thrown him for a loop after all.

“My sisters made me one.”

Stiles nods and licks his lips distractedly, “You should check it.”

“I’ve never even opened it. Stop changing-“

“Do you hear that, Scott’s calling me, gotta go.”


Stiles bolts out of his chair and runs out the front door, all the way to the closest coffee shop, where he hides.

He doesn’t even know why he’s doing it. It’s not like he asked Derek out on a date or anything (he’s working up to it, calm down).

He’s being ridiculous. He knows this, but look. If Derek answers him there then Stiles will have an open line of communication. One where he doesn’t need to use words.

He’s good with words. Okay, he’s passable with words.

He’s good at using them as a distraction, not when it actually matters.

Text from: Scotty Wan McObi
»»why is derek in our kitchen staring at is phone like it’s a math problem
»»did u break him again???

Text to: Scotty Wan McObi
««does he look mad

Text from: Scotty Wan McObi
»»hes asking whats wrong w his glasses
»»and bitchin about distracting shoulders
»»stop breaking him

Stiles has no idea if this bodes well for him or not. So he sips his coffee and glares at his phone to see if Howlr will ding faster.

It doesn’t do it faster.

But it does pop up with a new message. Eventually.


It’s all it says, followed by a picture of Derek looking annoyed and with his glasses almost falling the tip of his nose.

»»you put a shirt on. your shoulders are distracting.

Stiles makes some kind of embarrassing sound so high pitched that the teenaged girl next to him startles so bad she almost spills her coffee.

Phase one of his two year plan is a go.


The time he broke Derek isn’t as exciting as you think.

Stiles had been drunk so he doesn’t remember any of it. Scott told him.

He allegedly, stumbled home patted Derek on the cheek and told him he was the cutest bunny ever just before stumbling to his room causing Derek to stay frozen looking at a wall for approximately twenty minutes.

All of this allegedly, of course.

He doesn’t trust Scott not to exaggerate.


The first thing that Stiles does when he gets home, is to sneak into the bathroom and take his shirt off. He stares at himself a little self-consciously before he proceeds to take about three hundred selfies until he deems one good enough to send Derek.

What, Stiles complained about his glasses and got a glasses pic, Derek complained about his shoulders it’s only fair he gets a shoulder pic. Right? Right.

Stiles agonizes over it for a little bit, staring at the profile picture he took while high and trying to kind of copy it.

In the end he pics one that kind of shows a little too much throat and sends it because he’s a little shit like that.

»»you’re not the boss of me

He almost adds a winky face. Almost, but then decides he’s too cool for school to do that.

He sends it and about two minutes later something crashes downstairs and he thinks good, smirking at his own reflection in the mirror.


They don’t talk about it. Not really.

They still argue and press each other’s buttons when they’re talking face to face.

Stiles stares at him nothing short of adoringly when he thinks he’s not looking and Scott tells him Derek does the same but Scott is a hopeless romantic and shouldn’t be trusted with these things.

“It’s weird,” Scott tells him, “you should just ask him on a date like a normal person would. You sending each other dick pics and not talking about it is weird.”

“We don’t send each other dick pics,” Stiles protests, doesn’t add the yet because well, last picture Derek sent his sweats sure were hanging low on his hips. Stiles is pretty sure he drooled a little bit. It was pretty gross.

Isaac rolls his eyes from across the table, “Whatever makes you sleep better at night.”

“I don’t even understand what you see in him. And don’t you have a crush on Laura Hale. That’s his older sister, man.”

That is weird,” Isaac remarks.

Stiles waves a hand dismissively, “Laura Hale is an ethereal goddess beyond humanity’s reach. I admire her for what she’s doing. Derek- It’s different, I just wanna do nice things for him,” he nods at himself, “like baking him cookies and sucking his dick.”

Something crashes loudly down the stairs and they’re all on their feet in a moment’s notice.

Derek is sitting up from his place on the floor at the bottom of the stairs.

“Dude are you okay?” Stiles asks, crouching down, and checking over him anxiously, “Ohgod you’re bleeding. Come on, let me clean that up,” he coaches, getting him up by his armpits and herding him towards the kitchen.

Derek is blinking at him, mouth opening and closing like a stuttering fish, his ears red.

Stiles can hear Isaac laughing from here.

“It’ll heal,” Derek ends up saying, gruffly.

“Uh-huh,” Stiles nods, tipping his head back and cleaning his forehead carefully.


Things kind of escalate quickly after that because- yeah, because dick pics.

The first time it’s happening Stiles is not expecting it. He ends up sitting on the couch, pouting at the television with ice on his elbow as Scott laughs at him.

He had flailed so hard at the beauty of Derek’s dick he had smacked his elbow against the fridge. He’s pretty sure it’s gonna bruise.

But then he’s ready. He totally got this.

And then, because it’s them it kind of becomes a contest. It’s kind of ridiculous, but still thoroughly satisfying to hear the other cursing loudly from either their room or wherever they are in the house and angstily waddling towards the bathroom.


Stiles is drunk.

He’s drunk and he just wants to sleep and he thinks this would be a great place except it’s too goddamned loud and there’s a party still happening and he really doesn’t want to wake up with a dick drawn on his face, okay.

“Come on,” Derek’s face appears when he opens his eyes again, “off to bed.”

“No,” he whines, dragging the ‘o’ as obnoxiously as he possibly can.

Derek scowls at him and leans down, gets one arm under his shoulders and legs and just lifts him up like it’s nothing.

Stiles flails for a minute and clutches at him.

“No, too tall,” he whines.

Derek shushes and starts weaving his way through the party his eldest sister decided to throw. Stiles hasn’t even seen her yet and he’s not sure he wants to.

Never meet your heroes and all that.

He sighs and lets his head loll on Derek’s shoulder, finds that his mouth is really close to his neck, so he just- he contemplates that for a little bit as Derek gets him through the door of his room and just as he’s reaching Stiles’ bed he just-

Kisses it. A little bit.

Just a smooch.

Smooches never hurt anyone.

Derek drops him on the bed, possibly from shock and Stiles is too tired and too drunk for this.

He rolls the blankets around his like a burrito and sighs happily, “Thanks, babe,” he mumbles and promptly falls asleep.


“What’s up with your neck?” Stiles asks, sipping the coffee that Derek made him, the asshole.

It’s the fifth time or so Derek has touched it. And not just like, rub at it or scratch at it or anything. He just keeps touching the same spot with the tips of his fingers and getting this look on his face like it should mean something.

“Nothing,” he grumps and sips viciously from his cup. It would have much more impact if Stiles didn’t know he fills that stuff with hot cocoa.

“Weirdo,” he mutters, hides his smile right behind the rim of his mug.


They’re relationship is weird. He acknowledges that.

But it’s- it’s what they have. Dick pics and frustrated masturbating and arguments and banter (okay Stiles will concede that one) and quiet moments and breakfast and gentle touches.

And to be honest, they’re both too shit scared the other will say no if they ask. Even though it’s stupid. Even though everyone around them tells them it’s stupid, because they’re both so ass over heels over each other it gets to be disgusting.

At least that’s what Isaac keeps telling him while making a face.

It’s just-

It’s what it is and he’s lucky enough to have this.


So, he’s in the bathroom doing something pretty stupid.

A selfie stick is involved and so is his asshole but not like that.

Derek is currently winning their dick pic contest so Stiles decided to take measures and yeah he’s trying to take a picture of his butt.

That’s what’s happening here, and let him tell you that it’s decidedly more difficult than original planned.

Text to: Scotty Wan McObi
««u kno this is gon too far when im in t bathroom trying to take a pic of my own asshole

Text from: Scotty Wan McObi

Stiles rolls his eyes and puts his game face on, trying another position, a little bit trickier.

And of course because he’s Stiles he ends up overbalancing and falling head first into the corner of the tub.

Sharp pain blossoms on his forehead and catches the sides of his face and he thinks shit.

He touches a hand to it and his fingers come away bloody.

Double shit.

“This is gonna suck balls,” he tells himself, grabbing a shirt from the floor and trying to stop the bleeding with one hand while trying to pull his underwear on with the other.

“Stiles!” Derek’s voice sounds through the bathroom door, “Stiles I smell blood, open the door.”

“A lil’ busy here,” he grits out.

Stiles!” Derek growls, “if you don’t open this door, I’ll break it down.”

He barely has time to pull a towel around his hips before the door is ripped off its hinges and Derek’s bursting in, fangs popped and looking frantic.

“I fell,” he mumbles, wincing a little.

Derek kneels next to him, presses a hand over the shirt that’s stopping the bleeding.

“Of course you did,” he mutters.

“Everything alright?” Isaac and Scott appear at the door.

“Yes, I’m fine,” he assures, but it’s mostly drowned out by Scott’s.

No, Stiles is hurt. Scott go call an ambulance, Isaac get me a pair of sweats.”

“His or-“

“I don’t care just go.”

They both scuttle off hurriedly, throwing encouragements for Stiles not to die on the bathroom’s floor.

“What were you thinking?” Derek glares, “You could’ve died.”

Stiles’ brain is getting a little fuzzy, “I was thinking booty.”

Derek growls a little under his breath.

Isaac appears in the doorway with a pair of sweatpants and hurries to their side.

“Help me get him up and get those on him.”

“Urgh, no,” Stiles flails one arm.

“Stop being stupid. It’s not like I haven’t seen your dick before.”

Well, true.

He looks over at Isaac.

“We shared a locker room. I’ve seen your dick too.”

And okay, fair.

Stiles sighs, and lets them help him.

“My head hurts,” he tells him, eyelids starting to drop.

“Don’t fall asleep,” Derek commands.

“But I wanna,” he pouts.

“The ambulance is almost here,” Scott announces loudly, “You can’t fall asleep,” Scott says worriedly, trying to edge closer, but it’s a little hard in their tiny bathroom.

“Gimme a good r’son,” he dares.

“If you fall asleep I can’t ask you out,” Derek says.

Stiles’ eyes flash open and he looks over at him, “Like on a date?”


“Because you like me?”

Derek’s mouth quirks up a little, “Because I like you.”

“And then we’ll get mar’d?”


“And have a cat and a turtle?”

“A turtle?”

“Turtles are cool, man.”

“Sure we can have a cat and a turtle.”

Stiles hears sirens incredibly close and blinks a little stunned with how fast that was.

“Okay, let’s go. Don’t fall asleep or no date, okay.”

“You’re mean,” Stiles tells him, loops one hand around Derek’s neck and keeps the shirt pressed on his wound with the other.

“The worst,” Derek says, lifting him up and carrying him out and into the ambulance.

“Not r’ly,” Stiles says, leaning heavily on Derek and wincing as they go down the stairs, “I like you too. I like like you.”

The paramedics are climbing up the steps and as soon as they see them make way to the back of the ambulance.

“Good, us getting married would get awkward if you didn’t.”

Stiles laughs and it hurts.

Derek puts him in the back of the ambulance and holds his hand all the way to the hospital.

“Pinky promise,” he requests, holding up one hand, “pinky promise you’ll date and marry me.”

Derek curls his pinky around Stiles’, “Pinky promise,” he says solemnly.


The first thing Stiles does when he wakes up in the hospital, after drinking water from a straw is turn to Derek and shout.

“Ah, sucker, you pinky promised! I get you for- hmph.”

Derek cuts off his gloating by kissing him and okay, okay.

Stiles can get used to this.

He curls a hand around Derek’s neck, ignores how the machine monitoring him is beeping and giving absolutely everything away and just- just kisses him, his chapped lips against Derek’s finally.

This is so much better than dick pics. Especially if he gets Derek for the rest of his life.

(Spoiler alert: he does.)