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Hiiiiiiiiiii can I please request an imagine where yn is taking Gretchen out on a first date to the fair. It’s right after her and Jason broke up and Gretchen is assuming(worried) yn may be similar to how he treated her but after a bit she realizes Yn is the total opposite (winning her a prize and buying her treats) and they end up talking and having a sweet time at the fair.

Thank you!! Have a great day!

Miss Smooth Talker//

|| Gretchen Wieners x fem!reader

|| Warnings: underage drinking mention, hookup mention, swearing, Regina being Regina, Gretchen struggling with insecurities

|| Summary: first date, where Gretchen's worried that reader will be like Jason. But reader surprises her and they have a great time at a fair. Mostly fluff.

Requests open!

Started: April 23rd

Finished: April 26th

~~~

When Jason and Gretchen broke up you'd been there to comfort the girl. She told you all about it one night at one of Shane's house parties. You hated seeing her like that, she deserved better. So much better than a guy who only thinks of her when he's looking at her. She was your best friend and long time crush, so obviously you couldn't stand seeing her that upset.

One drink led to another and soon enough the two of you were wasted. Gretchen, in her very drunken state, had babbled on about how much she loved you and was grateful for a friend like you. You, without thinking twice (mainly because you couldn't think at all), kissed her. To your surprise she kissed back.

That's how you and Gretchen ended up having a one night stand.

It's been three weeks since then and Gretchen hasn't said a word to you, you could tell she was avoiding you you just didn't know why.

It was killing you not having your best friend.

Today you decided you would break the silence. Today would be the day you asked her out, because surely she wouldn't have kissed you if she didn't feel something too. Right?

Why else would she be avoiding you?

That lunch, you tracked her down and found her outside with her usual group. Karen, Regina and Cady. When Regina saw you she gave you an intense glare that sent shivers down your spine. You forced yourself to keep walking to Gretchen; having two cups of coffee in your hand. One was your favourite and the other was the order you knew was Gretchen's go to.

"Uh, no. Fuck off." Regina narrows her eyes at you once you stood next to Gretchen, you could see Gretchen tense up and you sighed. Crouching down to sit with her, catching Regina off guard because she wasn't used to people ignoring her. She tried saying more but you cut her off.

"Gretchen. Can we talk?" You looked at the girl, you looked away from Karen to look at you.

"We don't have anything to talk about, Y/N." You notice the slight tremble in her tone.

"Yes, we do. I know you've been avoiding me which if fine if you need the space but... a warning would have been nice at least." You ramble, wanting to get all your thoughts out before Gretchen could avoid you again. You quickly handed her her coffee," I.. um, got you this when I went out today. Maybe you could- I dunno, join me next time?"

Her eyes widened a little but she took the coffee, raising an eyebrow at you." Um... next time?"

"Like- a date- or not- we could just hang out-" Damn it. You had been so prepared for this. Here you were stuttering like an idiot.

Gretchen blushed when you said date and glanced at Regina, who scoffed and rolled her eyes. She looked back at you and smiled," a date?"

"I really like you, Gretchen. Sure we were both drunk but to me it was more than a hook up. Consider it at least?" You hoped she would hear you out at the very least, she nodded. You felt you could breathe a little easier now, you weren't as anxious as you had been.

"Oh! If you're going on a date there's a fall fair this weekend!" Karen piped up, you looked at Karen and smiled. A fair sounded perfect.

You looked back at Gretchen," Well. Wanna go to the fair with me?"

"Yes! I'd love to!" Gretchen grinned, feeling much more relaxed than she had been. She wanted her best friend back as much as you did, she was just scared of having a Jason repeat. In the back of her mind she knew you weren't like that. She knew you well enough to know that. But she couldn't help thinking it.

"Really?" You were almost surprised she'd agreed, especially with how much she had been avoiding you. You sighed quietly to yourself in relief and made a mental note to thank Karen later for the date suggestion." Alright! I'll pick you up at five on Saturday and we can head down?"

"Sounds perfect!"

And that's how you got a date with Gretchen Wieners.

The days leading up to Saturday were some of the happiest you've had in a while. You had your best friend back, if you could even call her that now. You were definitely more than friends, you just didn't know if you were girlfriend level or not.

You talked any chance you had, hanging out throughout the day (which unintentionally made you a plastic, Gretchen informed you of all their rules), at night you'd go over to each other's houses and on the nights where you couldn't you face timed. Just as you always had. Only, there was more. Holding hands as you walked through the halls, cuddling as you laid in bed together, doing each other's makeup in a more... well, it felt much more intimate now. Having her that close and seated in your lap...

Finally, it was Saturday. The two of you had been face timing each other all morning. Helping each other get ready from your own respective homes. You'd picked out a nice comfortable fall outfit, you can decide what it is. Gretchen wore an orange long sleeve with black jeans, she'd done her hair up in a ponytail and all that was left was the makeup.

(fall outfit I was thinking for Gretchen)

"Hey, Y/N?" She said suddenly, getting your attention as you were fixing up your own hair.

"Yeah, Gren?" You looked at your phone, which you had propped up next to you.

"I know you'd said you were going to pick me up at five but um could I come over now? And we do each other's makeup?" Gretchen rambled out, you could tell she was a little nervous asking.

"Absolutely!" You smiled at the thought, Gretchen doing your makeup was definitely one of your favourite little things in your guy's relationship.

You could see her smile and her shoulders relax as she grabbed her phone and started getting whatever she needed to come to yours.

"Alright, I'll be there soon!" She tells you.

Soon enough, Gretchen was now in your room. You sat at your makeup station with Gretchen sitting in your lap, working on your makeup. You could see the concentration on her face and you couldn't help but grin, your hands wrapped around her lower waist to keep her steady in your lap.

"Close your eyes for me." Gretchen said, her voice nearly a whisper. You did as told.

She worked on your makeup for a solid ten minutes, making sure everything was perfect and to the way you liked it. She'd come up with the idea of matching fall makeup, which you thought sounded adorable so you agreed to it.

Once she was satisfied with her work, she looked at you and smiled before giving your cheek a soft kiss.

"You're gorgeous." She whispered, earning a faint blush from you.

"If I'm gorgeous, then that must make you angelic." You replied, a bit of a flirty tone in your voice. Gretchen blushed deeper than you did and giggled, you were pretty damn proud of getting that reaction out of her.

"Yeah well if I'm angelic that makes you a Goddess." Gretchen one upped you, making your blush deepen. Your hand rested to the back of her neck as you pulled her closer to you, lips just inches apart.

Your eyes locked on hers.

"Okay Miss Smooth Talker." You teased her, she laughed a little and kissed you deeply. You kisses her back, getting lost in the moment with each other.

This had been the first time since the party you had properly kissed each other. Was that even a proper kiss? You both were drunk, so you weren't sure if it counted. Sober kisses were so much better than drunk kisses.

As the kiss broke, your eyes remained on each other. Both grinning like love sick idiots.

When you finally snapped out of it a minute later, the two of you finished getting ready. You helping Gretchen with her makeup.

Once all that was settled, you took a photo for instagram. Arm draped around Gretchen's shoulders as you kissed her cheek.

The caption reading:

First date ready! 🍁🍂🫶

You weren't insta famous by any means, so your post only got a few likes from your friends and mutuals. Though you noticed a like and comment from Karen.

@ karenshetty EEEE U GUYS R CUTETS! 💕

You laughed a little and showed the comment to Gretchen, who smiled and looked up at you.

"She meant cuties." Gretchen translated for you, noticing you were a little confused by the spelling. You nodded in understanding and looked at the time on your phone.

4:42pm.

"Well, shall we head down?" You looked at Gretchen, who smiled and took your hand in hers.

"Let's go!"

~~~

At the fair, you and Gretchen are having an absolute blast. Or at least, you were. Gretchen was overthinking and worried that you might be like Jason; but every time she thought that way you would instantly prove her wrong without her even having to ask. You were perfect to her.

"Gren! Let's go over here!" You grabbed her hand, pulling her through a crowd.

"Woah, Y/N/N slow down!" Gretchen laughed as you pulled her along, the amount of energy you had always surprised her. She wondered how you could be that energetic all the time.

"I'm gonna win you the best fucking prize!" You exclaimed, throwing your free hand into the air with excitement. You were ready to kill it at these games.

Gretchen laughed and smiled as she watched you, finding it absolutely adorable. She took a small video of you being all bouncy.

Your eyes landed on the balloon dart game and smirked, seeing all the different prizes around it. You were going to win the biggest one for Gretchen. Pulling her along with you, you stepped up to the stand and the stand host explained the game to you.

You were only partly paying attention. You knew how to play; three darts for three chances to hit the balloons. The top corner balloons were worth the most points. So you aimed for those as Gretchen cheered you on.

Your first shot; you missed the corner one you had been aiming for but you hit the one two balloons below it. Earning you 30 points.

There's five rows of balloons, the bottom being worth 10 points, second row 20, middle 30, fourth 40, and top 50. The top corners were 60.

"30 points!" The stand host announced as you hit the balloon, you rolled your eyes and huffed.

You were determined to get that 60.

You tilted your wrist a little more and tossed the next dart, eyes narrowed at the 60 balloon.

The dart landed right above it.

"Come on!" You groaned, having missed the balloons entirely. This game was so much easier than it looked.

Gretchen rested her hand to your shoulder and smiled at you, giving your cheek a kiss which made you blush as you looked at her.

"A good luck kiss." She explained, her blush matching yours. God, she was adorable.

You shot your finale dart, hitting the 60. You immediately threw your hands into the air and smiled wide, looking at Gretchen. Good luck kisses for the win.

"60 points! That will bring your total up to 90, dear! Pick a prize!" The stand host said in that over exaggerated carnival voice. Y'all know the one.

You kept your eyes focused on Gretchen and bent slightly, gesturing to the prizes in a dramatic way." Well, m'lady. Pick a prize, any prize!" You mocked the carnival voice, earning a laugh from Gretchen an annoyed stare from the stand host.

Gretchen kissed your cheek in thanks and picked out a prize, going with a decently sized teddy.

"Adorable choice!" You kept up the voice, she looked at you and smiled. Her hand draped around your waist as you stared into each other's eyes.

"I'm really enjoying today." She told you as you both walked away from the stand.

"Yeah?" You smiled at her, a faint blush on your cheeks.

"Yeah. I was... worried this would end up like my last relationship- I know you and Jason are nothing at all alike, I know that- it's just-" She rambled out, trying to explain. You sighed, knowing exactly what she meant. You didn't fault her for it.

"What he did stuck with you, it's only natural to be scared. I'll never treat you the way he did." You assured her, seeing her relax as she kept her eyes locked with yours.

You had an idea.

Looking away from Gretchen, you laughed a little at what you were about to say," See! I'm still thinking about you even while I'm not looking at you."

This earned a laugh from Gretchen as she jokingly shoved you, she knew exactly what you were referencing. She had told you about when Jason said he only thought of her when he looked at her.

"You're such an idiot." She teased you, though she meant none of what she said.

You looked at her and brought her close to your side," Mm, maybe. But I'm your idiot, aren't I?"

She blushed and nodded," Yeah... yeah you are."

The rest of the day went really well, you and Gretchen decided to do the ferris wheel as your last activity for the night.

You sat in the booth as it went to the top at a slow motion, arms wrapped around each other as you laughed and talked about anything and everything.

You'd been mid complaining about an upcoming test, that Gretchen had totally forgotten about so she was complaining right along with you, when the ferris wheel stopped as the two of you were at the top. You glanced behind Gretchen and admired the finale parts of the sunset, looking at Gretchen you saw how it almost made her glow with how she was positioned in front of it.

God, she was gorgeous.

"Hey, I wanna get a picture of us up here. Scoot closer." You told her, she blushed and did as you asked. You held her close to her side and took a photo of the two of you, sunset in the background and set it as your new lock screen.

Gretchen smiled and looked at you.

"If I'm already your lock screen, does that mean I'm getting a second date with you?" She asked.

"A second and then some." You assure her, your eyes went to her lips and hers went to yours.

You kissed her, deeply and passionately. She kissed you back with a similar energy.

You couldn't wait to spend more time with Gretchen.

#x reader #fem reader #canon x reader #fanfic #wlw fiction #mean girls x reader #mean girls #gretchen x reader #gretchen wieners #gretchen x fem!reader

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