☁︎request for @squish98☁︎
imagine being bestfriends with les and crushing on an oblivious dean...
Y/N's POV:
I spot the group gathered on the grass and see that Dean is sitting with them as my heart begins to race. I've been crushing on Dean for so long now but he hasn't noticed. Probably because I haven't made a move at all since I've been too scared. Except, today I feel a new sort of confidence and I've decided today is the day that I'll finally flirt with Dean. Finally make him notice how I feel about him even if he doesn't feel the same way.
Just as I begin to walk over, Les sees me and waves to me wildly. "Y/N! Come on!"
I wave back and run over.
I say hi to everyone and sit in my usual spot next to Dean and Les. I just sit there for a minute, looking kind of insane, trying to figure out what I'm going to say to Dean while watching Les argue with him about how two plus two is four, not five.
Les nudges me after a while. "Y/N, you're kinda quiet today, aren't ya? You usually like joining in on the debate."
"What? Oh, yeah. Just thinking, you know." I answer, nodding my head.
He smirks. "About what?"
I smirk back. "Nothing of your concern."
Les shrugs. "Ok, I won't ask."
I just smile and wait for Dean to finish arguing. When he does he turns to me. "Well, what d'you think, Y/N? Is two plus two five or four?"
I shrug, twirling my Y/H/C hair around my finger. "Whatever you think, Dean." I add a sigh on the end. It's something I see people do on movies all the time.
He sighs. "Well, Shelley thinks that it's five but it's four, right Les?"
Les nods in agreement. "Definitely."
"Crap." I think. I wasn't obvious enough. "Oh, Dean, you're so smart and did you get a haircut? Because your hair looks amazing."
Dean smiles kindly. "Thanks, Y/N. I didn't get a haircut but I'm wearing it differently today. Do you like this way better?"
"Totally, Dean." I bat my eyelashes.
Les snorts and begins laughing uncontrollably.
I turn to him. "What?" I say angrily. I don't understand what's so funny.
He shakes his head. "No, no, nothing."
I shrug off his laughter and continue to 'flirt' with Dean. It's not really flirting but more talking.
"Closest I'm gonna get." I think.Time skip!
I walk down the road with Les while Dean is distracted by trying to get his bag off of the top of a lamppost.
"You have a massive crush on Dean, don't you?" He says.
I blush bright red. "Um, no I don't."
Les points at me. "Aha! Got you! Your voice goes all high when you're lying."
I look away and smile. "Shut up, Les." I glance behind me at Dean, who has finally grabbed his bag off of the lamppost. "And my voice does not go all high when I lie."
"Oh yeah, definitely." Les sighs. "Look, Y/N, if you want me to set you up with Dean then I totally can-"
I interrupt him by shaking my head. "No, it's fine. I don't like him so it won't be worth it."
He looks as if he's about to say something else when Dean suddenly turns up and begins to walk between us. "So, what did you guys talk about while I was gone? Man, those ninth graders are crazy. One of them climbed a fucking tree just to put my bag on that lamppost."
I giggle. "Well, at least you got it back. Maybe I should give them a piece of my mind next time."
"Hopefully there won't be a next time." He laughs. "But it's the thought that counts, right?"
I nod. "Heck yeah, man." I can't believe it. I've been as unsubtle as I possibly can without saying 'I love you'. I glance to my right and see my house looming over us. "I gotta go. Catch you guys later!"
They both wave goodbye and I go straight up to my room to ponder what other ways I could make Dean notice me. I also call up Mercedes for advice which I guess was sort of helpful. She advises that I should be myself and then Dean will fall in love with the real me. After that, I must have fallen asleep or something because I'm woken up to the phone ringing. I assume that it's Mercedes so I pick it up almost straight away.
"Hey, Mercedes." I sigh, rubbing my eyes.
"What? No, it's Les. Wanna come to the drive-in with me and Dean tonight?" Les answers.
I'm suddenly wide awake, my heart beating quickly. "Y-yes. A thousand times yes."
He laughs. "I'll pick you up in fifteen minutes, ok? See ya, Y/N!"
I put down the phone and immediately start looking through my wardrobe for something to wear. I eventually settle on a denim skirt, Queen t shirt and a pair of chunky high top adidas sneakers. I also bring a matching denim jacket just in case it gets cold.
I hear a loud honk outside my bedroom window and run down the stairs, out the door, and to Les's car.
I climb into the back seat. "Good evening, fellas."
Les looks at me through the rare view mirror. "Evening, Y/N. Looking good back there."
Dean turns in his seat to look at me. "Yeah. I didn't think that it was possible for you to look even better than you usually do."
I blush. At least it was dark and he couldn't see it. "Thanks, you guys. So what movie are they screening?"
"Grease, I'm pretty sure." Dean says. "It's a good movie."
"Yeah. Pretty romantic." I say, glancing at him.
Dean and Les argue quite a lot about what way the drive-in is and eventually, I have to show them so we get there in no time at all. Les finds a spot near the front of the rows and rows of cars. "It's the best spot." He insists. He glances at his watch. "Holy shit! The movie's gonna start in fifteen minutes! The queue for the food's gonna be the length of the whole entire drive-in by the time we get there. I'll go, you guys get comfy." Les winks at me before disappearing to the snack hut.
I try to figure out why Les winked at me before Dean interrupts my thoughts by suggesting that we should sit on the hood of the car, which, in my opinion, is the best spot to watch movies ever. So we clamber up onto the hood, Dean having to pull me up since I was too short to do it myself. We sit in silence for a while: waiting for Les to come back with snacks when Dean breaks the silence: "Do you think Les will get extra butter or extra salt on the popcorn?"
"Butter definitely." I answer, nodding my head. "Les is a butter sort of guy. I know it just by looking at him."
He suddenly breaks eye contact with me and looks at the sky. "You're crushing on Les, aren't you, Y/N?"
My eyes widen and I start to blush. "No I'm not. What makes you think that?"
"Well, for starters, you're blushing." He smirks, obviously amused by my reaction. "You always wanna 'talk to him privately' and you kissed once."
I roll my eyes playfully. "Yeah, we kissed in like the third grade, Dean. We're just good friends, all right?"
"Yeah, but do best friends look at each other like this?" He smirks in over-dramatic admiration.
I can't help but laugh. How oblivious can this boy get? "When have I ever looked at him like that?"
"Today at lunch when I was sitting next to him." He says. "Jesus, Y/N, you have the memory of a goldfish!"
"I do not have a crush on Les, ok?" I insist.
"Do too!"
"Do not!"
It goes on in this childish sequence for a while until I finally stop him. I decide to finally come clean. If he can't notice on his own, then I'll just have to tell him. "Listen, Dean. This is so stupid."
"What?" He asks.
I sigh. "You thinking I have a crush on Les when I don't."
"But you do." He insists.
"But I don't." I look away from him. "You're the one I have a crush on. When you thought I was looking at Les today, I was actually looking at you and all those 'private talks' with Les were about asking if I could copy his math homework because I thought you would blab about it and I tried flirting with you but you didn't seem to notice and... I don't know what else to say."
"You don't have to say anything." Dean sighs.
For a minute, I think that he's going to leave but he pulls me closer to him and kisses me. It's the best kiss I've ever had, well, I guess I've only ever had one real one but it's still the best. We don't even care that the movie started, we just keep kissing for what seems like forever.
Dean pulls away from me, out of breath and smiling. "I love you, Y/N. I always have and always will. Man, I can't believe I thought you had a crush on Les. I suppose I was jealous or something."
I shrug, also smiling wider than him. "I can't say much, I guess. I might've thought that you liked Mercedes."
He shakes his head. "Nah, I'm reserving her for Les."
"Have fun without me?" Asks Les, somehow back already from the snack hut.
Dean and I glance at each other. "You could say that..." I say.hi! this one was kinda long but i love the idea so much so thanks for requesting it, @squish98!
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