Happy Birthday Dylan O’Brien

Did You Pretty Woman Me?-REQUESTED

It was coming up on your and Dylan’s three year anniversary. You had a few ideas for what to do, but Dylan insisted he was going to take care of everything. 

“There is one thing I need you to do,” he tells you one day after you were trying to get him to confess his plans.

“Yeah, anything! What do you need?”

“I need you to buy a couple of new outfits for yourself. I invited one of your friends to take you out and gave her the money and a list of what kind of clothes to get and some suggestions on where to get them. Everything is taken care of, you just need to go.”

Your mouth drops, “Did you just Pretty Woman me?”

“I don’t know what that means, but probably.”

“It means you’re paying your prostitute for a whole new wardrobe so you can be seen with her out in public. And because I’m a prostitute I need help going to stores or they’ll refuse me,” you say with mock seriousness. 

“Okay, not exactly but kind of,” he teases. 

You laugh and playfully hit him, which only results in him grabbing you like he’s going to fight you. He pins you down so that you can’t move but then showers you with sweet kisses on your neck making his way up to your lips. They’re so gentle and light that it makes you shiver. 

“You still won’t tell me our plans?” you ask.

“Nope,” he says, leaving a small kiss on your nose. At that, you wiggle out of his hold and go call your friend. 

You and your friend end up spending the whole day shopping for outfits. The friend would casually guide you on outfit ideas but refused to spill the beans on what any of them were for- no matter how much prodding. 

You were dying to know what you were doing with Dylan and the outfits just made you even more curious. 

It was the day before your anniversary and the anticipation was killing you. You had gotten Dylan a gift, one that you knew he’d love. The outfits were all hung up in your closet...well they had been.

“Babe? Where did my new clothes go?” you ask.

“They’re in your suitcase.”

“Why?”

“Because we have a plane to catch.”

“A plane? Does this mean you’ll finally tell me what we’re doing? You kind of have to right?” you say with a devious smirk.

“We’re going to New York and I have a bunch of stuff planned for us. Wipe that look off your face though because the rest is on a need to know basis. And that knowledge will only come by the minute.”

The smile slides right off your face. 

“I love you, but sometimes you’re a pain in the ass you know.” 

“Oh you won’t be saying that for long,” he says planting a kiss on your cheek. 

You end up in New York and have the most whirlwind romantic weekend. 

The day you land he takes you to a couple spa to relax from the flight. That evening he takes you to go see your favorite movie and then you go out for burgers and milkshakes. 

The next day he goes with you while you get your nails done. You even convince him to get a pedicure. You start to worry that he might not be enjoying everything so you pester him to cancel some of the things he had planned for you so that the two of you do things that he likes to do. 

You want to make sure that he knows that it’s about the two of you and not just you. And that you want to see and know he’s into. 

He assures you not to worry and that the next day is more about the both of you. With that aside, the evening brings a sweet, romantic dinner. 

Dylan wakes you up the next morning earlier than you’d like to take you sight seeing. You spend the whole day acting like a pair of tourists. By late afternoon you’re walking around Central Park hand in hand. 

You’re walking over the bridge looking over the water and all of a sudden you turn and see Dylan on one knee.

“Oh my God, shut up,” you squeal.

“Y/N, I love you. I love everything about you. I love who you are as a person, I love the way you make me feel, how you compliment me and make me want to be a better person. You’re amazing and I want to spend every second with you. Will you marry me?” he asks holding out a sparkly diamond.

“Yes! Yes! Oh my God!” 

You hold out your hand and he slips the ring on. A perfect fit. He gets up and you wrap your arms around him and he twirls you around.

“I love you so much Dyl.”

You don’t know who initiates it, but both of you are kissing each other. It’s loving, tender and beautiful. 

“This spot is a total cliche by the way,” you giggle, arms still around his neck. “I still love you though,” you whisper. 

Happy Halloween-REQUESTED

“Babe what are we gonna be for Halloween this year?” you ask Dylan.

“I don’t know? Go out? Look stupid and drink?”

“Well yes. But I need more concrete plans. I want to know what we’re going to do. And I really want to know what we’re wearing. Are we doing a couple’s costume or no?”

Dylan gets a devilish grin on his face, “Oh yeah, definitely a couple’s costume.”

“Okay, what are we gonna wear then?”

“Oh god I don’t know,” he says. 

“Sexy? Funny? Something stupid?” 

The two of you end up having a ridiculously long debate on what the costumes should be. He kept fighting for something sexy, mainly you in something sexy. You, on the other hand, kept fighting for each of you to be the opposite gender of any costume.

Dylan was fine with a skirt but wasn’t into the idea of wearing heels.

After many vetoes, you and Dylan were able to agree on you being Janet Snakehole and him being Bert Macklin, Andy and April’s alter egos from Parks and Rec.

Over the weekend, the two of you ended up throwing a Halloween party. You guys decided it was the only way to get everyone you wanted to see together. It was a real beast, pun intended, trying to get everything ready in time.

However, everyone ended up loving the haunted house feel and the themed food and drinks. There were places set up in the house for fun fall/Halloween games. You guys had also splurged for a DJ (neither one of you wanted to be tied to the aux) so there was a place set up out back to dance. It was a little brisk outside but you guys figured if they were dancing it would probably be fine.

Your costumes were a hit and you were smart enough to set up a photo booth that your guests took turns occupying all night. It was one of the best nights with your friends you’ve had in a long time and you wouldn’t have it any other way. 

Then it was time for actual Halloween. You left the decorations up from the weekend, inside and out of the house you were too lazy, and you stacked up on candy. 

You and Dylan were going to have a night in watching scary movies and handing out candy for any trick-or-treaters.

Neither one of you were really dressing up for the evening after your weekend. Dylan wore a mask to cover his face whenever he answered the door. You wore a festive headband. 

Dylan kept giving out handfuls of candy to the kids so the stash was dwindling quickly. You both realized that you weren’t going to be able to watch any movies with the doorbell ringing every two seconds so you weren’t complaining. Once you guys ran out and turned off your outside lights. 

Then you and Dylan were able to get a little more settled and into the movies you had lined up. You kept the lights off, got a bowl of popcorn, and snuggled close on the couch.

Every now and then something would happen in the movie and you would jump a little. At the end of one of the movies Dylan started teasing you about it. 

“Yeah, okay, I might be a little jumpy but you do stuff too,” you say.

“What do I do?” he asks defiantly. 

“You get all tense and stiffen up every time something happens.”

“I’m preparing myself for the physical pain that is about to occur because of your jumpiness,” he retorts. 

You laugh, “Okay, that’s funny. Because I’ve seen you do it even when I’m not sitting next to you.”

He opens his mouth to say something but closes it.

“That’s what I thought. At least I admit it. If you don’t want to be physically harmed while we watch the next movie, I’ll sit on the other end of the couch.”

“No don’t do that,” he says, grabbing your hand and pulling you back to him. “Okay, okay, okay, I tense up,” he confesses with a kiss.

“Good, now go refill our supplies while I put in the next movie,” you say with a peck on the cheek.

“Popcorn, soda, and more candy come up.”

Be Careful-REQUESTED

Dylan and your’s friendship took awhile to form. It started on the Teen Wolf set. You were a stunt person for one of the other actors. That actor sure had a lot of stunts.

You first started as an outsider. You were a replacement for the original stunt person. You had a lot of stunts with Dylan O’Brien’s stunt person and he ended up being one of your first work friends.

After almost a month of work, you went to your first work party. You mostly hung out with the stunt crew and Dylan’s stuntman, the party was pretty cliquey.

About an hour into the party Dylan himself meanders over to say hi to his stuntman. The stuntman, while sitting next to you, introduces you to Dylan.

“Oh yeah, Y/N. I’ve seen you around, nice to finally meet you.” He holds his hand out to shake yours and you stick your arm out.

“Holy shit!” he exclaims, seeing the two massive bruises on your arm in varying stages of healing.

“Yeah,” you laugh, “that’s what everyone says. If you think those are bad you should see this massive one I got on my back. That one is getting real ugly.”

“How-? Oh-” he says, your line of work suddenly dawning on him.

“I work doing stunts and I bruise like a peach.”

“Damn, you gotta be more careful!” he says, getting up to go mingle with some other people.

That was the end of your conversation with him that evening, but at work he started talking to you more.

First it was brief and casual. You’d bump into each other at the same set or at the food table or running to the bathroom and get stuck chatting each other up. It developed into work friends, where you’d coordinating eating lunch together.

Eventually you became true friends. Exchanging numbers, texting funny pictures, hanging out after work.

And then the show ended but you guys had already somehow magically turned into each other’s best friend; so it wasn’t a big deal that you weren’t going to see one another at work every day. 

Now that you weren’t working together, it was harder to get together.

Or it should have been.

You guys were always hanging out with each other or each others friends- even if the other one wasn’t there. Your friends became his friends and his friends became yours. They all joked that you were going to get married or you acted like a married couple. 

Your friendship with each other was borderline obsessive. You were always talking to each other or about each other. It was a healthy friendship but everyone always thought there was a hint of something more. 

Sometimes you wanted to explore more of that hint, but then you’d suppress it because of the fear of it ruining your friendship. 

One day, while on set at your new job you got really injured and had to go to the hospital. You were in a lot of pain and you were pretty sure that this time you seriously hurt yourself.

You were hanging out in the ER with a friend while you were waiting for your diagnosis. During this time you sent Dylan a snap of you in your hospital gown and in your bed throwing up a peace sign. 

Immediately he starts blowing up your phone and tries to FaceTime you but you didn’t realize it because that’s when the doctor came in. You found out that you had a few bruised ribs and you tore your ACL. They said that they were going to emit you into the hospital, give you some pain medication, and that they’d give you the surgery for your ACL in the next day or so. 

The doctors and nurses were taking you to your own room and giving you medication, knocking you right out, before you could even check your phone. Luckily your friend let Dylan know what was going on. 

You had been stuck in a half sleep, half wake for awhile. You couldn’t actually wake up but you could hear what was going on around you. You were getting more and more terrified that you were going to be stuck this way. 

It was silent so you couldn’t tell if you were alone or if maybe you had actually fallen in some weird sleep. But then you felt a sweet, faint, soft pressure on your forehead and a familiar voice say, “I told you to be careful.” 

The familiarity of the voice and the fact that they talked to you instead of just around you calms you and your able to finally sleep peacefully. 

Hours later you finally wake up. Your friend is gone but Dylan is on the seat beside your bed passed out.

You take the pillow behind your head and throw it over to Dylan. It hits him right in the head. 

“Hey, wha-”

“Oh my god,” you say clutching your side. 

“Are you okay?” Dylan asks, worried with a smidge of panic in his voice. 

“I forgot about the broken ribs.”

“They said that they bruised.”

“Yeah well they feel broken.”

“Are you okay?” he asks again.

“For the most part. The meds helped with the pain but I couldn’t sleep. And I don’t know how I’m going to deal once I have surgery. I’m screwed for at least a week or two.” 

“Okay well the post surgery thing is easy, you can stay at my place. Or I guess I could come babysit you at yours? Either way, I can help you out with that. And what do you mean you couldn’t sleep? You’ve been asleep since I got here and that was hours ago.”

“I don’t know. It was like I was asleep, I couldn’t move or wake up. But I could hear what was happening. But then somebody came in and told me to be careful and then I was actually able to fall asleep.” 

It quickly dawns on you that it the voice and peck that soothed came from Dylan. “Maybe it was a dream,” you retreat. “Well kinda nightmarish up until the kiss, I mean voice,” you babble, “I didn’t think I was going to wake up. I thought I was going to be stuck like that forever. But eventually I did actually fall asleep,” you finish lamely. 

Dylan looks startled. “That sounds awful. I’m glad it wasn’t like that for you the whole time.” 

He doesn’t let anything on besides that. The room suddenly feels very nervous and awkward.  

“So you want to nurse me back to health?” you ask jokingly, hoping to break up the tension.

“If that’s what you want to call it, sure. I’d love you. I mean, I’d love to.”

You laugh it off, “Thanks you’re a life saver. Seriously, your the best.”

It’s a few weeks after your surgery. Dylan really had been a life saver. You both decided it made more sense for him to take you to his house while you recovered post-surgery. He knew where everything was and it would be awkward for him being part guest part caretaker at your place. 

Plus his spare bedroom was on the first floor. And it had a bathroom right beside it. Much easier to get around. 

You were there for two weeks. You only needed to be there for one week, but Dylan insisted on you staying. He would have kept you there for another week but you that’s where you drew the line. Plus you were getting off of your crutches soon so that made a compelling argument.

“Alright Dyl, can I please take you out for dinner as a thank you for these past two weeks?”

“Yeah but-”

“No, you’re not buying dumbass. What is the point of me ‘taking you at as a thank you’ if you pay?” 

He was going to say a comeback but his words got caught and he couldn’t come up with anything.

“I’ll let you drive. Mostly because it kinda still hurts. So you can pick me up. Wear something nice.”

“Alright, text me when you wanna do this,” he says with that goofy half smirk half smile that he has. He knows better than to argue with you at this point. 

A couple of days later you were at your house getting ready for your dinner with Dylan. You were oddly anxious about it and it was starting to feel more like a date than dinner with a friend.

You were really regretting your decision to go somewhere nice and your rule to wear something nice. You had been vegging out for the last two weeks since the surgery and gained a couple of pounds and were just not vibing with the way anything was looking on you. 

Eventually you decide to go with some spanks-which were hell to put on-to combat that post surgery poundage. You paired it with a little black dress that was fairly low cut, expertly showing off your cleavage, tight around your middle (but it was black and black makes everyone look good), and had a bit of a flare at the bottom. Since you couldn’t wear heels and you hated all your flats, you ended up wearing a white adidas superstar shoes. 

All the celebs do it right?

You polished off the look by expertly curling your hair. You even did your makeup and added a nice purse. 

This was really starting to feel like a date. 

Just as you were spraying perfume on and double checking yourself out in the mirror, Dylan called from in your living room, marking his arrival. 

“Okay, I’ll be out in a second!” You take one final sweeping look over yourself to make sure you look good and you go out to meet him.

“Holy shit Y/N. Damn.”

“Um...thank you?”

“Sorry,” Dylan says, blushing. “You look...You...You clean up really well.”

“Thanks,” you laugh, “So do you.”

The two of you go out to Dylan’s car where he opens the door for you and bows, one arm obnoxiously extended. 

“I would curtsy but I haven’t covered that in physical therapy yet,” you joke. 

The rest of the evening is typical for the two of you...for the most part. You joke and tease each other mercilessly all night. You talk about what you’ve been up to, how his work has been. You ask about each others family and friends. You reminisce about stupid things that you’ve both done together, which usually leads to more teasing.

The weird thing is that there feels like there is a little bit of flirting in these interactions as well. Which, of course, is completely uncharted territory. 

At the end of the dinner the check comes and Dylan tries to pay again but you swat his hand away. 

“Thank you but no thank you. If you pay it’s a date. If I pay it’s a thank you.”

He says thank you and then remains quiet until the car ride. 

“So if I were to pay, it would have been a date?” he asks, breaking the silence.

You were surprised at his question. You had said the comment jokingly but now you wondered if you actually meant it. Or wanted it. 

“Well yeah, I can’t get all dolled up and go out to dinner with a guy and let him pay and it not be considered a date. I did my hair,” you say, deciding to keep it casual.

He falls silent again. He stay silent through the rest of the car ride, leaving you with just your thoughts and the soft sounds of the radio.

He pulls up to your place, opens your door again and walks you to your front door.

“Okay I have another question.”

“Actually I have one for you this time,” you say, deciding to make your confession. 

“Alright, you first.”

“What if I wanted to get dressed up again and do my hair and go out to dinner and let you pay?” you say quickly before you can change your mind.

He crinkles up his face, thinking. Most likely he’s trying to figure out what you just said because you threw a lot of things at him in a very short, winded time. 

And then he smiles slowly. 

“Can I ask you my question now?”

You’re taken aback, seeing as this isn’t the response you were looking for, but you nod yes.

“Can I kiss you?”

You’re nodding again and laughing as he bends his head down, cupping your head in his hands and pressing his soft lips on yours. 

As you break apart he asks, “So if this wasn’t a date, when can I take you out?”

Hello loves,

I’m so sorry it’s taken me forever to write this! I took these two requests and combined them but it’s actually a pretty long one (especially since I wrote it as one instead of breaking it up). It took me awhile just to write this one, which usually never happens so I hope you really like it. 

And thank you guys so much for the requests please send more!!

Hi followers

Pleaaaaassseeee send me some requests!! I have a few in my inbox I need to get to but I need some fresh ideas. I’m in like writer’s fog-not block just fog.