winn x reader

he is actually the definition of pure

Welcome Home - Part 1

Originally posted by ghostthinxx

Request: (by anon) Hello! I love your writing, you’re one of my favorite writers on Tumblr. :) I was wondering if you could do a Winn Schott imagine, where after the crossover or whatever you go back to Earth 38 with Kara and you end up falling in love with Winn? Like a lot of flirting and cute moments where Winn gets all flustered? Thanks! :D <3

Pairing: Winn Schott x Reader feat. Kara, Alex, J’onn, Oliver, and Barry

Warnings: None

Words: 2807

A/N: So, I loved this prompt so much that I decided to make it a series. And if you’re wondering what her costume looks like, I made that too. Sorry this isn’t as flirty/flustery as I meant it to be. Maybe I’ll do better in part 2.  ¯\_(ツ)_/¯

The Dominators were defeated, the presidential honors were given, the celebratory party was winding down, and Earth-1 was saved. The only thing left to do was to say your goodbyes and go your separate ways.

Over the last few days, you had become good friends with Supergirl, or Kara Danvers as it was. At the party, she had mentioned how on her Earth it was just her and her cousin defending the planet and how nice it was to have a team. You couldn’t have agreed more. It would be nice to fight crime with others like Team Arrow or the Legends. It would even be nice to have a support group like Team Flash, even if you were the only one in the field.  But you had no one. No friends, no family, no one to rely on other than yourself.

Knowing this, Kara invited you to come back to her world to fight alongside her. Earth-1 had plenty of protectors and you had no reason to stay, so you quickly jumped at the opportunity.

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The Friends of My Lover (Winn Schott x Reader)

Request: Can you do a Winn Schott x reader where Winn introduces the reader who is his girlfriend to the rest of the superfriends and everyone is really surprised/weary because the reader is a DEO agent who is known to be quite cold, mean, hard and is always in a bad mood/grumpy but to everyone’s surprise she turns all soft around Winn? I hope you have a fabulous day!

This took me five hundred years and I am sorry.

Trigger Warnings: Meeting the Boyfriend’s friends

Originally posted by schottjr

“I am so excited to meet your new girl!” You heard Kara squeal to Winn.

This was not at all what you wanted. Winn was supposed to be a one night stand, someone who was there with you after too many glasses of whiskey, and then took you home to have sex until you let the next morning slightly embarrassed and awkward. Instead he took you to his home, layed you down on his bed and promptly took the couch. The next morning was filled with the awkward conversation of how you two wanted to do this, but not when you were so drunk you couldn’t tell him where you lived.

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It Was the Chicken

Requested by @a-deliciouslyfadingcollection:  Can I request another Winn Schott Jr. x reader? Where the reader got up at like three in the morning throwing up and it turns out she has food poisoning? I would really appreciate it.

Pairing(s): Winn Schott Jr. x Reader

Author’s Note:  You have the best requests!  Ugh!  I’ve had so much fun writing everything you’ve requested so far!  And now I have all of the Winn feels!!!  I hope you enjoy this!

Originally posted by luthorshero

    You wake up with a terrible feeling in your gut and a groan.  You turn your head to the nightstand to see what time it is: 3:00 AM.  You groan again, and silently get up and run to the bathroom as the awful feeling resurfaces.  You make it to the toilet just in time to empty your stomach of everything you had eaten earlier in the day.  You’re about to vomit again when you feel someone - Winn - beginning to pull your hair back.

    “Are you alright?”  Winn asks.

    You look behind you to see him with a very concerned look on his face.  You shake your head pitifully as you fall back into him with a frown.  “I feel like shit.”

    Winn places a kiss to the top of your head before resting his chin in the place his lips had been momentarily.  “I’m sorry,” he says sympathetically before you wrench forward and vomit into the toilet again.

    “Was it something I ate?”  You ask, racking your brain for what you hat eaten that could have upset your stomach.

    “Maybe,” Winn replies.  “Did you eat anything today that I didn’t?”  And that’s when it came to you; the chicken.  You groan and Winn gives you a questioning slash concerned look.

    “I went out with Kara and Alex today, remember?  I had chicken that had some kind of weird sauce on it; I thought it tasted weird!”

    Winn chuckles, “Well, there was definitely something weird about it.  You good now?”

    You nod, “Yeah, I think so, but I still don’t feel good?”

    “Is there anything I can do to help?”

    “Get me puke-bowl and cuddle with me in bed?”

    “I can do that,” Winn says, pressing a soft kiss to the top of your head.

    “I love you.”

    “I love you, too.”


Sorry for the late upload you guys. I just got out of a ten hour road trip and just got the internet back. I hope you enjoy my first Winn Schott imagine all the same!

“Excuse me.” You said, trying to get anyone’s attention in the busy lobby of Cat Co. World Wide Media. You were hoping to visit your mother, but no one was able to help you. Well, actually, they may have been able but they weren’t willing to help you.

You had been in Central City for school then later for your career. You hadn’t seen your mother in years, but since your mother’s name had gotten flown back into fame because of the new Kryptonian, Supergirl. You cried out in frustration, “Can anyone take me to Cat Grant’s office?!”

“You needing help to Cat Grant’s office, Miss?” You turned your head to the voice. A brunet man, your age, button up shirt and tie. You sighed in relief, finally able to get some help.

“Yes, please, I was supposed to be meeting her, but the receptionist isn’t at the desk and now no one here will take the smallest glance at me-”

“That’s what it’s like at-” The man paused, then, using the hand he wasn’t holding a tray of coffee with, gestured to the busy lobby, “Cat Co World Wide Media. I can take you to to Ms. Grant’s office.”

“Thank you so much. I’m (y/n).” You followed the man’s lead as he walked toward the elevator.

“I’m Winn, I work just outside her office, so it’s not problem for me to take you there.“ You two stepped into the elevator, filled with more employees like packed sardines. You and Winn didn’t talk in the elevator, you didn’t feel like talking where everyone in the elevator could hear.

As the elevator went up more and more people piled out until it was just you an Winn alone in the elevator. The elevator stopped at the floor and Winn stepped out, asking you, “May I ask why you’re here to visit Ms. Grant?”

“Oh yeah,” You remebered, still following behind Winn, “I’m her daughter. I’ve been in Central going to school and working and decided to come back home to see my mom.”

“M-Mom?” Winn stuttered out, putting his satchel and coffees on his desk. “Media shark Cat Grant is your mom?”

You grinned at his words, to his surprise. You loved your mom, even with her career ambition, you had gotten the same ambition from her. Besides the point, ‘Media Shark’ wasn’t the worst thing you had heard your mother been called. “Yeah, are you surprised? I look just like her from when she was younger from what I’ve been told .”

“No, I’m not surp- I’m lying, yes, I am surprised. You and her seem so-” Winn paused looking for the right word, “-different. Sorry, in a good way though! I mean, you’re really nice and stuff!”

You smiled at him and his flustered-ness. “You don’t have to apologize for making an observation about my mom and I, or about calling her what she is. And thank you, for calling me nice.”

Winn smiled, once he had noticed that you weren’t mad at him. “Well, this is her office. I think her assistant, Kara, is out right now, so I would just head on in.”

“Thank you, Winn.” You said, walking toward the open office doors where you assumed your mother was sat, turned to her TVs so she couldn’t see you. You paused before entering her office, “Would it be okay if I came over to see you later, to get to know each other? Maybe during your lunch break? Or after work for dinner?”

You hoped he would understand what you were wanting, a date, and you hoped he’d say yes. Winn looked almost taken aback and you hoped you hadn’t insulted him or hurt his feelings. “As a date?”

You nodded your head, smiling shyly at him. Winn seemed like a good guy, and you hoped he had said yes.

“I would love to go to dinner with you.”

“Great!” You exclaimed, going to dig into your purse to find a business card you had. Once you found it, you handed it to Winn. “My cell number’s on the back. Call me.”

“I will.”

You moved into your mom’s office to greet her.

“I don’t know. I always want to help people. I mean, I know where to draw the line, but I think if anyone admits they need help, they probably deserve it. That’s why I became a nurse, and now am becoming a doctor. If I have the opportunity and the chance to help someone and I don’t, what does that make me?” You answered, then taking a sip of your soda.

You were on your date with Winn, and he had asked you why you had gone into medicine as a profession. Winn had said he was an IT because he liked it and he was good at it. To be a practising nurse while going to medical school was tough, but you loved helping people, no matter how many times you had to tell someone that they were experiencing a common cold or they just had a mosquito bite and they weren’t dying of skin cancer. You loved the goods too much to outweigh the bads.

“T-That’s amazing. Like, literally, amazing. You almost sound like Supergirl when you talk like that.” Winn complimenting you, reaching across the table to hold your hand. You smiled at the gesture and the words.

“That means a lot Winn, especially from you.”

requested by: anonymous

Originally posted by dailydcheroes

Y/N: Wait, is that me?

Winn: Oh, yeah. I sometimes like to make you and Kara fight.

*He picks up Supergirl’s action figure along with yours and makes fighting noises as he plays with them.*

Y/N: Oh my gosh, you’re such a dork! 

Winn: But I’m your dork! 

Y/N: Yes, you are.

Lesson (Winn Schott x Reader

The Music Meister is back to teach another lesson about Love. This one is with my fav nerd Winn, y'all don’t know how much i love him, and i brought back a song from his Newsies days.

Trigger Warning: Prison, mentions of death/killing, awkward crush stuff

Originally posted by dailysupergirl

Your head hurt, that all you really knew. Your eyes were closed and you were laying on a concrete floor, and your head hurt.

Slowly you opened your eyes, you were in… somewhere you didn’t recognize. It was strange, the last thing that you clearly remembered was walking into your bedroom after an embarrassingly bad attempt at asking your crush, Winn Schott, on a date which resulted in you complimenting his shirt and him gently punching your arm. Kara had pushed you to try again, but one shoulder bump was enough humiliation for one day. Now you were in… a prison cell?

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Dating Kara Danvers (Supergirl) Would include...

Originally posted by stileshowls

  • You meet on your first day as an assistant at CatCo and you quickly become good friends with her, James and Winn
  • You both develop a huge crush on each other and whenever you flirt with her she melts and becomes a blushing mess
  • You eventually ask her out after weeks of flirting and sexual tension
  • It doesn’t take you long to figure out that she’s Supergirl, especially after she saves you before a date and says “see you at seven!”
  • You confront her about it at the same time she decides to tell you
  • “You’re Supergirl”
  • “I’m Supergirl… wait, what?”
  • “Kara, you just tie your hair back and put on a pair of fake glasses, did you really think I wouldn’t notice?”
  • “…”
  • She tries to keep your away from all the stuff that she does as Supergirl
  • You end up rushing to the DEO anyway.
  • Being close with Alex
  • Take out. All the time.
  • Movie nights every Friday with Alex and Maggie
  • Kara is definitely the big spoon in the relationship
  • Lots of stroking/ playing with her hair
  • All the kisses
  • Whenever she’s really stressed you give her a massage to calm her down
  • Meeting Clark and being a bit awestruck by being in a room with Superman, but you eventually become good friends
  • Kara always holds your hand or just links your fingers together, she likes to have contact with you at all times
  • Always being starstruck by her muscles (bitch me too the fuck)
  • Most of your dates end up being interrupted by some supervillain, but she makes it up to you later ( ͡° ͜ʖ ͡°)
  • Kara is definitely the top in the relationship, but you will occasionally switch roles
  • Sometimes she grips your hips too hard and leaves bruises and she apologises for hours after she notices
  • She still blushes every time you’re intimate
  • One time you wore underwear with a super ’S’ on them and she lost HER MIND
  • You get mad every time you give her a hickey but it disappears after a couple of seconds
  • She acts like a lost puppy whenever you’re apart for more than a couple of hours (But so are you)
  • You both love and trust each other with all your hearts and you become that couple that everyone rolls their eyes at because you’re so smitten

a-deliciouslyfadingcollection  asked:

Okay I am going to ask another Winn x reader where they are in a relationship and reader is a Dancers so they are keeping it a secret but when Kara walks in she is slightly surprised but says I should have known it because reader is always gushing about Winn to her sisters. They beg her not to tell Alex but Kara accidentally lets it sleep or Alex follows behind Kara and she does. Irving. Winn asks why and she tells him he knows the consequences and she trusts him.

Really Shouldn’t Be Doing This

Warning(s):  None

Author’s Note:  As always, I’m sorry about the wait.  I’m also sorry about the ending; it didn’t turn out fantastic.  But I hope you enjoy anyway.

Usually, your relationship with Winn is confined to your apartments, or secluded sections of the park, or basically anywhere you have a small to zero percent chance of running into your sisters.  You loved Kara and Alex, but one being Supergirl, and the other being a secret agent, and you being the youngest… well, to say they’re protective would be an understatement.  So when Winn finally asked you out on a date, and when the two of you finally made it official, you opted to keep your relationship a secret.

But today doesn’t fall under the “usually”.  Somehow - somehow meaning you and Winn were particularly flirty and were texting each other extremely flirtatious texts - you and Winn ended up in an empty hallway together making out.

Winn has you pinned against the wall and is holding you up by your thighs and you have your legs wrapped around his waist and your arms around his neck.  Winn starts to plant kisses on your neck when you speak up.

“Winn, we really shouldn’t be doing this here,” you say, trying not to let out a satisfied moan as he starts to leave a mark on your skin.

“Yeah, you really shouldn’t be doing this.”

You and Winn both freeze at the voice that you both recognize.  Turning to look at Kara, you smile awkwardly as Winn quickly puts you down.  You run your hand through your hair and laugh ironically while Winn nervously scratches the back of his neck.

“What do the two of you think you’re doing?” Kara asks, crossing her arms.

“We were just… We were… Uh…”  Winn starts, but you quickly elbow him in the side and he groans.

Kara’s face breaks out into a smile and she starts to laugh.  “I’m sorry, but you guys are adorable.  I’m honestly surprised this didn’t happen sooner with the way you two talk about each other.”

You grin.  Winn does too.

“So now that Kara knows, can we tell people?”  He asks.

“No.  Alex still doesn’t know.  So we’d appreciate it if you didn’t tell her,” you say.

“Alex doesn’t know what?”  Alex asks as she walks in the room.  Kara smirks.

“I caught them making out,” Kara says with a smirk.

“Kara!”  You exclaim.

Alex just smirks.

“Yeah, they’ve been doing that for a while.  I was wondering when they were gonna tell us about that.”

You blush and Winn chuckles.

“But, Schott,” Alex says, “if you even look at her wrong, I will kill you.”

“Duly noted, Danvers.”

Originally posted by gingerann

Something Special

Originally posted by fairestcharming

Request: (by @chigonaconchaHey! Can I request a Winn Schott one shot where Winn wants to ask out reader but doesn’t know how and finds out she’s never been asked out on a date?? Also if u could tag me in it that would be awesome thank uuuu

Pairing: Winn x Reader, feat. Alex, James, and Kara

Warnings: N/A

Words: 2155

A/N: This hits way too close to home…

Winn sat at his computer at the DEO, fidgeting with a toy that he kept on his desk. He stared off into space as he contemplated asking you out. It wasn’t so much whether to ask you out or not, but rather how to ask you out. He always got nervous talking to beautiful women, but with you, it was worse. You were really special to him and therefore needed to be asked out in a special way. He couldn’t just ask you.

“Earth to Winn!” Alex waved a hand in front of his face.

“What? Oh hey, Alex.” He shook his head. “What can I do for you?”

“Can you trace this for me?” She handed him a piece of paper with something written on it.

“Sure can!” He took it from her and started running a trace on his computer.

“So, what’s on your mind?”

“What do you mean?”

“You were totally zoning out a minute ago.”

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Baby Daddy (Winn Schott x Reader)

So another super girl imagine, this one with my fav nerd Winn. I don’t think there shuffled be any trigger warnings, besides pregnancy and the occasional swear. I hope you guys enjoy this one, because it was my favorite to write so far.

Originally posted by lauraswift3

Thysdione was your home planet, there you were equivalent to a princess. Living on Thusdione was all you had ever known, and the custom of the Gods deciding who shall marry was not a strange one to you. So when the Gods blessed you with a mate you were beyond happy, your mate was strong and powerful, a warlord over his people. Each night he would take you to bed, but leave before morning’s light. You hated it, hated knowing you were not good enough for him.

When you discovered you were with child you knew you had to leave. You did not want your baby to grow up with a father who clearly has no love for his family, only for sex and violence. Packing a meager bag of your belongings and enough money to board a space cruiser heading far away, you slipped away, not leaving a note or anything. 

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Something To Believe In

 Winn Schott x Reader

Summary: Reader and Winn are having a friendly movie night when Y/N wants to watch the Newsies musical from Broadway because she hasn’t seen it and she used to watch the movie, but Winn doesn’t want to, because of reasons. ;)

A/N: Okay so recently I have become obsessed, I mean obsessed with Newsies, and Jeremy Jordan and Ben Frankhauser are such amazing actors and singers and WOWZA. Also, I lovelovelove the show Supergirl and Winn is like one of my favorite characters so here is a story kinda combining the both of them. ALSO: this is really shitty bad because I am in a writing slump so sorry I tried and it sucks but here you go. Also it’s kinda short

Warnings: The movie isn’t on Netflix I’m sorry, like 2 minor swear words

Originally posted by pontmarius

Winn?” Y/N shouted from the doorway of Winn’s small apartment. “Get your ass in here its movie night. We have been doing this every Friday night for three years Winn. You’re not getting out of it this time.” Y/N said as she walked into the kitchen and began making popcorn. “I swear. That boy is impossible.” Y/N mumbled to herself. “Impossible eh?” Winn said from behind her. Y/N turned around and stared at him. After a couple seconds she scoffed and turned back to the microwave. “Popcorn’s almost ready Winn, you go get the blankets and stuff.” Y/N said with a small smile on her face, that she knew Winn couldn’t see. She heard Winn sigh and shuffle away to go get the couch ready in the living room. 

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Your Parents, Our Future

Requested by @a-deliciouslyfadingcollection: Another one I am sorry. I just can’t write to save my life. Though it is where Winn is meeting her parents who are at National City and he spends the entire time thinking the reader’s father hates him but it turns out he is just being paranoid because the father shakes his hand and says “treat my child right." 

Warning(s):  Nah.

Author’s Note:  I am so sorry for my unannounced leave of absence.  I’ve been a mixture of unmotivated and lazy.  I am also super sorry for the long wait for this fic.  I hope you enjoy it! 

And just ignore the fact that the gif has dialogue that has literally nothing to do with the plot of the story; it was the best I could do.

Originally posted by dailysupergirlgifs

When you told Winn that your parents were coming to stay with you for the week, you knew from his reaction that he was going to be a hot mess.  His reaction was that of a teenage boy afraid of facing his girlfriend’s father for the first time.

“Are you sure I have to be here?”  He had asked, “I’m sure James would be okay with me crashing at his place for a week.

“Yes, I’m sure,” you had responded.  “Winn?”


“I told them that you’d be there with me when I went to pick them up from the airport.”

Winn’s eyes widened at your confession and his face paled.  He swallowed, his Adam’s apple bobbing in throat.  “O-okay.”

That’s how you ended up at the airport, waiting at Gate C, and holding your nervous boyfriend’s sweaty hand.  You sigh, take your hand back, wipe it on your pants leg and look up at him.

“You knew you were gonna have to meet them eventually,” you say.

“Yeah, but I thought I’d be able to avoid it until after we’d gotten married and had at least two kids.  At least then they couldn’t decide they didn’t like me because I gave them grandchildren,” he responds, anxiously watching the gate for your parents’ appearance.

“Wait,” it was your turn to be flustered, “After we’d gotten married?  Two kids?  You’ve thought about that stuff?  You think we’re gonna make it that far?”

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The Other Allen - Winn Schott Drabble

Originally posted by supercanaries

Request: (By @smurryheartbeatz) Could you write a Drabble where reader is Barry allens sister but she fell in love with Winn and moved to the other earth to be with him, and she’s homesick?

Words: 935

A/N: Ok, so this got a wee bit angsty, but not too bad. 

“Hey, are you okay?” Your boyfriend came and sat next to you on the couch.

You had been staring out of your apartment window all morning as you let the mug of coffee in your hands grow cold.

“What? Oh, yeah, I’m sorry.” You sighed. “I guess my mind’s somewhere else today.”

“You wanna talk about it?” Winn draped his arm around your shoulders.

You put your mug on the coffee table and leaned back into his embrace. His arms tighten around you as you tucked your feet up under yourself and rested your head on his shoulder. The sound of the rain against the window lulled you into a nostalgic state.

“I was just thinking about this one time after Joe took us in, we were playing in the park and it just opened up and started pouring down rain. So, he yells for us to come back to the car before we get soaked, but he went from having one kid to three pretty much overnight and he just doesn’t have a handle on it yet.” You chuckled, “Now Iris and Barry are good kids, so they come when they’re told, but me, being a rambunctious six-year-old, I’m not done playing yet. So, cut to a Benny Hill style montage of Joe chasing me around the park, slipping in the mud, while Barry and Iris are watching from the car and making bets on who will outlast the other. It must’ve looked ridiculous, because when he finally dragged me back to the car, Barry was the happiest I’d seen him since what happened with our parents.”

“So, what you’re telling me is that you were always this much of a handful, huh?” He gave your arm a squeeze as he laughed.

“Yeah, I guess so.” You smiled up at him.

You sighed heavily, causing him to instinctively begin playing with your hair, which began to soothe you.

“It all seems like so long ago. When did our lives become so chaotic?” You pondered.

“I would say probably when we started hanging out with superheroes.” He chuckled to himself.

“Yeah, probably.” You laughed similarly. 

Despite his calming touch, you couldn’t help but feel a wave of sadness washing over you. Perhaps it was the cold and the gloomy sky the rain brought with it.

“I honestly don’t know how Barry does it all.” You shook your head. “He went years with people not believing him about Thawne, and then he gets these powers and has to save the city constantly, and then Zoom…”

You felt a lump in your throat that you tried to swallow. “God, he had to watch as that monster shoved his hand through our father’s heart. He had to watch both our parents die…”

“I couldn’t possibly begin to imagine what that must have been like.” Winn was apologetic and somber. “But he’s strong and I think a majority of that strength comes from others. I think most of it comes from you.”

“Yeah? Some pillar of strength I turned out to be?” You muttered.

“What’s that supposed to mean?”

“It’s just… sometimes I feel like I abandoned him.” You could sense Winn wanting to protest, but he waited for you to finish. “He’s always facing off against some bad guy and the moment he’s finally happy and things are quiet, when we can finally spend some quality family time together, I leave. I just up and leave for some parallel universe. Don’t get me wrong, I love you and I love being here, but I feel like I turned my back on my family to do so.”

“That’s bull and you know it. Nobody forced you to come here and more importantly, nobody forced you to stay there. Your family knew the risks and the rewards. They knew what would make you happy and they let you go. They love you and would do anything for you,” his slightly agitated tone softened to a more loving one, “including letting you run off to a parallel dimension with some nerdy computer programmer.”

You couldn’t help but laugh, “Well, who could blame them? He is pretty hot.”

“He thinks you’re pretty hot, too.” He playfully rolled his eyes.

You gave him a quick kiss on the cheek.

“So then, why don’t you call Barry using that, uh, inter-dimensional extrapolator that Cisco made you?”

“The communication function is busted.”

“Oh, well let me take a look at it and see what I can do.” He offered. “In the meantime, you can still use it to make a breach and go visit him.”

“I don’t know. He’s probably really busy fighting some new big bad. I swear, there’s always someone.” You rolled your eyes. “Besides, I’ll probably just get in the way. Or get myself captured because I don’t know what I’m walking into.”

Or, hear me out here, you could spend a nice weekend with your brother.” He waved a hand. “If I’ve learned anything from working with Kara, it’s that there is never going to truly be a quiet time. There is always going to be some bad guy to fight or some kitten to save. There’s never going to be some ideal time to live your life. You have to live it in the here and now. You have to make your own happy moments, not wait for them to magically appear. So go, visit your brother. And if it’s a bad time, make the best of it.”

“Did I ever tell you that you’re the smartest man I know?” You smirked. “And I know a lot of smart men.”

Hacker Sass [Winn Schott x Reader]

Requested by @queen-of-all-the-fandoms: “Juuuuuleeees, I want an imagine with Winn’s super sarcastic and sassy S/O sassing J'onn. This is a thing I need in my life. Please and thanks! 💙” 

A/N: Here is the final request on my list! Yay! Took me long enough lol. I made this so the reader is a hacker because I wanted a bit of backstory and my friend @thefangirlforlife gave me the idea to have the reader do some cool computer thing and do the joke. So thanks babe! <3 Any way I hope you guys like this. (I honestly feel like it’s trash lol)


You have been with Winn for a good while now. You know about his being Guardian, know about how Kara is Supergirl and Hank Henshaw is actually J’onn J’onzz aka The Martian Manhunter. The circumstances of how you met Winn weren’t the greatest. You’re a hacker or were a hacker, and for a while you didn’t use your abilities for the best purposes.

You didn’t use it for bad things, just not ‘legal’ things. You were sort of a cyber vigilante, taking down bad sites, transferring money out of corrupt businesses back to the people they scammed. Going by the hacker handle ‘ph03n1x’ which means phoenix.

Having made quite a name for yourself on the net. Though you set yourself up for failure when you heard about the DEO. A government organization all about Extra-terrestrial monitoring, you had to see this. Easily you broke through the firewalls, you’ve hacked the CIA before. This was child’s play for you. However upon getting in, your computer signalled you that there was a track happening. So, you shutdown your computer and left the DEO alone.

Little did you know the person on the other end got your location. A few hours later there was a knock on your door. Groaning you had answered it, seeing a guy with brown hair standing there. Kind of nerdy looking. He introduced himself as Winn Schott, the minute he said he was the one who tracked you, you pulled him into your apartment. He went on to explain that his superiors had no idea about any of this, that he had heard about your acts as ‘ph03n1x.’

He offered you a job to help in a good way. Though you weren’t interested, and escorted him out of your home. However, he began to drop by and check up on you. Make sure you weren’t getting into trouble. The relationship turned from him checking up on you, to friends, to more than friends.

Which brings you to where you are now. Walking into the DEO to get Winn for your one year anniversary. You may know of the other’s secrets but Winn never told them about your former hacking.

“Hey guys” You greeted while walking in. “Hey [F/n], congrats” James hugged you. Laughing you thanked him, “I know, who would’ve thought anyone could put up with him for a year.” You teased, knowing Winn was only a few feet away.

“I’m right here!” he called, raising his hand from in front of his computer. J’onn was standing beside him, in his Martian form. Walking behind the chair you wrapped your arm around his shoulders. “You ready?” whispered to him, joy in your tone.

“Yeah, just a sec. I have to get these coordinates for J’onn then I can leave” Winn answered, not looking away from the screen. Watching his cursor as he continued to fail to find the coordinates. “Agh! Why won’t it track?!” He yelled frustrated. “Focus Agent Schott” J’onn scolded, crossing his arms.

“Aw for the love of.” You rolled your eyes, seeing everything he was doing wrong and couldn’t help yourself. Standing up straight, while moving to the keyboard. Winn pulled his hands away as you worked your magic on the keyboard, having the coordinates they needed up in seconds. Turning to see them a bit shocked.

Even J’onn, you laughed before saying “What’s wrong J’onn? You look a bit green with envy.” Chuckling at your own joke. Winn gave you a worried look, did you just sass J’onn?! Do you want to die?!

After you exchanged a look with J’onn he began to laugh. You made J’onn laugh. Winn couldn’t believe his eyes, he’s only seen Alex do that. The other DEO agents were just as shocked.

“Good work [F/n], remind me to offer you a position here at the DEO after your anniversary.” He said before heading out to help Kara at this location. Winn was still sitting in his seat awestruck and staring at you. “Why are you staring?”

“I just, did you just sass J’onn, make him laugh, and then get a job offer?” his brows furrowed in confusion. “I did” you nodded before taking his hand and pulling him from his chair. “How?” Disbelief written all over his face as you made your way out of the DEO, making you laugh. “I’m just that good” you shrugged.

He chuckled, “I guess so.”

Office love

Requested for Anon - Request for Winn! Kara and James finally convincing him to ask you out because you two are always so nerdy together, so they think you’d be a perfect match!

Word Count - 600

Characters - Kara , James x Winn (friendship)

‘Winn will you quit staring at her.’ James asked Winn, as he kept staring at you. Winn never broke contact, he nodded his head.
‘Yeah well it’d be good if you moved your head.’ James said with a raised eyebrow. Winn turned around but James understood. You were the exact same as Winn, nerdy and knew everything and anything. Winn finally turned around and looked at James.
‘Sorry.’ He said, blush making its way up his cheeks.
‘You should ask her out.’ James said, leaning back in his chair, Winn leaned forward grabbing a paperclip from the desk.
‘She won’t agree.’ Winn said, playing with the items on James’s desk.
‘You could try, you don’t know what she’d say.’ James said, he noticed Kara coming towards the office. She smiled throw the door and he nodded her in.
‘What you are talking about?’ She asked excitedly, seeing Winn and James together.
‘Winn’s crush.’ James said, Kara turned around and looked at you through the glass. You were smiling and laughing with your colleagues at your desk, they flung an apple and you caught it taking a bite from it.
‘You still haven’t asked her out?’ Kara asked in shock, Winn turned to look at her and shook his head.
‘He’s scared.’ James teased him.
‘I am not.’ Winn said, he furrowed his eyebrows but then placed the items back to there normal places.
‘You should.’ Kara told him.
‘Why? She’ll only reject me.’ Winn told them.
‘Winn, she won’t reject you, she likes you.’ Kara said, he perked up slightly.
‘Really?’ He asked, James chuckled lightly sitting up himself.
‘Yeah, I overheard her the other day talking to the others.’ Kara said, taking a seat on one of the couches.
‘Well, eh, what’d she say?’ Winn asked.
‘She likes you, thinks your cute.’ Kara said, watching and Winn smiled looking at you.
‘Anything else?’ He asked. Kara looked at James and smiled.
‘Yeah, she’s waiting for you to ask her out, she said she would ask you but she doesn’t want to come on too strong.’ Kara said, she watched as Winn looked down at his feet before standing up.
‘Okay, I’ll go and ask her.’ He said standing up.
‘Okay.’ James and Kara said. They watched as he walked out the room, and over to your desk. Everyone around you went quiet as they saw him come over, they nudged you and you looked up.
‘Winn, what can I help you with.’ You asked getting your pencil ready.
‘Tomorrow night.’ Winn said. You raised an eyebrow.
‘What about tomorrow night?’ You asked and the other giggled slightly at how nervous he was.
‘Ehh, go on a date with me.’ Winn asked nervously.
‘Okay.’ You told him.
‘Okay?’ He asked shocked, you nodded your head. You stood up.
‘When and where?’ You asked, he looked at you before clearing his throat.
‘The new restaurant down at the corner on fifth?’ Winn asked, you nodded.
‘Okay, see you then.’ You said after placing a kiss on his cheek. He stood still at your desk as you took a seat, you started typing away when he didn’t move you cleared your throat.
‘Winn?’ You said, he looked down quickly.
‘You can move, right?’ You asked him, he looked down and say that he was still standing there, he nodded before turning away and heading back to the office where Kara and James were standing. When he entered the office, he raised his arms.
‘WHOOOO!’ He said, you turned around and you saw him with his raised arms, you looked down and smiled.

Originally posted by luthorshero

Winn Schott Relationship Headcanons
  • Having a loving and nerdy relationship
  • Weekly movie nights with Jimmy, Kara ,and Alex
  • Nerding out together over superhero movies
  • Forehead kisses
  • Working at the cubicle across from him
  • Mrs. Grant silently shipping you two
  • Him complimenting you on EVERYTHING
  • “Your hair looks lovely today”
  • “My hair looks like this everyday”
  • Going to Kara every time you wanna talk about Winn
  • Just being Kara’s best friend
  • Comforting him after what happened with his dad
  • Feeling jealous about Siobhan Smythe when she comes to CatCo.
  • Him reassuring you he doesn’t like her
  • But then him being jealous over Barry
  • Giving him jaw kisses because yes
  • Hugging him around his waist
  • Cuddles whilst watching Doctor Who
  • Inviting him and the SuperSquad to Thanksgiving dinner
  • Doubting yourself because you’re not a fighter like Alex and Kara
  • Him reassuring you that he thinks you’re still amazing
  • Always buying pastries for breakfast
  • Being his date to the CatCo parties
  • Any time there’s a Fort Rozz escapee on the loose, he calls you to make sure you’re okay