THE BET (A Charlie Lenehan Imagine)

The Bet - Full Story

Authors note: this imagine goes back and forth between your point of view and Charlie's. This was also originally an Instagram imagine so proper punctuation and grammar might be lacking and I apologize in advance. Thanks for reading!

(Your POV)
After not seeing Charlie in months while he was away on tour, you finally got to hang out with him again and catch up on old times. You two were laying out on his roof like the good old days, watching the stars and talking about anything and everything. "Hey Charlie," you said, resting your arms behind your head. "Remember that bet we made at the arcade?" He was silent for a moment, rolling on his side to face you. "You mean the one we made after I beat you in that NASCAR game when we were like 9?"
You and Charlie have had that bet since you were little about who would get their drivers license first. Since he was a few months older that you he always teased you because that would mean he could get his earlier, but you always stuck your tongue out back at him and told him he'd be a bad driver. "Yeah, and I said that it didn't matter that you beat me at a racing game because I would get my license first?" You ask. "Oh yeah, and the loser had to do what ever the winner said for a week, I remember that," he says, smiling about remembering the past.
You grinned, although it was probaby too dark for him to see it. Reaching into your pocket, you pull out your wallet and hand it to him. "Well guess what," you say proudly, gesturing for him to open it.
He eyes you suspiciously but does anyway. When he sees what's inside his eyes widen and he starts shaking his head. "You got your license."
"Yup and you didn't so I guess you know what that means." "No way that's not fair I've been away on tour so I couldn't!" He protests. "A deals a deal! Come on Charlie, we even super secret handshake swore on it." You pluck your wallet from his hands. Charlie sighs in defeat at the mention of the super secret handshake, returning his attention once again to the stars. "Alright, a deal is a deal," he replies, accepting his defeat. "Great because you start tomorrow!" You exclaim, getting up and kissing him on the cheek. Climbing back through the window and into his room, waving as you leave, you happily walk back to your house, excited about what you get to make him do for one whole week.

(Charlie's POV)

I'm left alone on the roof after Y/N leaves. It was dark so I pray she missed the red tint that coated my face when she decided to surprise me with a kiss on the cheek. It's not like she'd never done it before, but it felt different laying alone with her at night under the stars. Probably just puberty doing what it does. The bet was one of those ridiculous things that only the winner ever remembers first so they can finally claim some insane prize from the loser. A whole week of doing whatever she said. Too bad I didn't win, there was so much I could make her do. I heard the door click, so she must've gone back home. I climbed back through the window, taking a look at my face in the mirror, touching my finger to the place she kissed. My heart beat finally slowed down, and I threw my shirt and jeans across the room, lying in bed with just boxers. I checked my phone one last time before going to sleep. 3 new messages. Two from Leo, but he just sent me more emojis. I sent a couple his way before checking the other message. "Y/N - be at my house at 9 am sharp!! Be dressed to impress C:" I rolled my eyes, setting my alarm for 8:00 before throwing the blanket over my shoulder and going to sleep.
I saw Y/N in front of me, and she was doing that thing where she plays with her ring when she's nervous. She walks up to me, eyes cast down, opening her mouth but no words come out. I take her hands in mine to calm her down, and she takes a deep breath. "Charlie...I really like you. I've liked you for a long time," she stuttered. I ran one of my hands through her hair, kissing the tip of it. "I really like you too. Want to be my girlfriend?" Wow I was being forward. But gotta take your chances I guess right. And since when did I really like her what am I even saying? We've been good friends for a long time and shes a blast to have around but do I like her enough to ask her out? I couldn't think anymore as she leaned in, her lips so close to mine. /RING RING/
I open my eyes, realizing all that just happened had just been a dream. I guess this hell week was my one chance to understand my own feelings, and hopefully hers too in the process.