The Outsiders x Reader

First Date

♥Ponyboy♥
You and Pony hit it off that night at the movies. That is, even though he drenched your shirt. It wasn't that he was shy, he just didnt talk a whole lot. Not that you minded. He was nice to be around and he thought the same about you. You guys would stay at school a little later than usual sometimes. He would end up walking you home since it was close to his. Darry was constantly on his case about the time, though. You never met Pony's brothers but you understood why he was like that, you just wish he could ease up a little. Just a little...
It was the last school day before spring break but Darry had to work later into the night. Lucky for you guys, Soda didn't mind you two going to the lot and Johnny said he would be at the movies with Dal. You guys left school and it wasn't too dark so you headed to the lot. There... was when it started getting dark.
"Shouldn't we get going, Pony?" You asked standing up. You guys were just sitting against a building when you noticed the sun start to go down.
"You ever seen a sunset, Y/N?"
"..." You looked over to the horizon. "Yeah... right now. Can we go?"
"You ever had a first date, Y/N?" He didn't look at you but you could see the light blush on his face. It was a little out of character for him to ask something like that but you tucked a piece of hair behind your ear and answered him anyway.
"Uh, I've had so called boyfriends before but dates...? I dont know."
"Well how about we sit here a little longer... and maybe we can call it a date... if you would want that, I mean..." he scratched his head and looked down at his lap, his blush becoming more apparent. You've said it before, you'll say it again. He's a total cutie!
"Pony?" You said crouching down to make him look at you.
"Y-yeah?" He asked as you put your hand on his cheek
"Do you have a crush on me?" You decided to mess with him a bit. You rubbed your thumb on his cheek and batted your eyes at him with a teasing grin.
"W-well I mean... kinda..." he was trying so hard to look at anything but you.
"Good." He looked back at you with widend eyes and you pinched his cheek. "Because I like you, too, Horsekid." You sat beside him against the wall and rested your head on his shoulder. You let your mind wander as you looked at the sunset.
"I've always liked you..."

♥Darry♥
You saw Darry around every now and then and you eventually got to know him. He was a hardworking man who had responsibilities. He was always so stressed out but every time you would talk to him, he never let it out on you. He was a true gentleman and talked to you like one, too. You respected him for all the hard work he did to take care of his brothers. That was love, and you loved him for it. It did, however, make it rare for you two to actually hang out. You understood and all. You just wish you could have a day to yourselves... together, maybe...
It was a rainy Friday night and Darry had been working way more than the usual two jobs. He would occasionally call you on Friday nights for a quick catch up but you figured bills were pilling up and that's why he was working so much. Therefore you let him be and just sat at home. You had already eaten supper and taken a shower so you were just kind of working on your laptop when there was a knock at the door. You checked the window and were pretty surprised to see Darry there.
"Darry! Hi! What're you doing here?" You said opening the door. He looked like he had taken a shower and was clean shaven. He also had flowers...?
"Y/N, I'm really sorry I've been working more than usual. I've been trying to earn some side cash to, well, I was hoping to ask you out to dinner. Tomorrow, if you dont have any plans, I made reservations to a fancy restaurant and I'd be honoured if you'd go with me." He smiled and even without the flowers and formal invitation, there was no way you would turn down a date with him.
"Darry, of course!" You said accepting the flowers. "But you really didn't have to do all that."
"You're worth it. I dont ever really have time for relationships with work and the boys and all but you're patient with me. I really do like you and I would really love to, maybe, try and be a couple. If the first date goes well, of course."
"Come here." You pulled him into a hug and gave him a quick kiss on the cheek. "And you can come in by the way."
"Okay, but I can't stay too long in case the lights go out back home or something."
"Thats fine, but we have to discuss our date details." You smiled and closed the door. The next day he picked you up looking insanely handsome and you guys headed to the restaurant. The two of you actually had a lot of fun. You ate an amazing dinner and joked around and flirted and it was probably the best and most mature date you've ever been on. When you guys were ready to leave, he opened the car door for you and helped you in. You guys drove around just a bit after, though.
"We really have to go on more dates." You laughed.
"Yeah, I feel a whole lot better, honestly. But that could just be because I'm around you." He said going to grab your hand.
"You're sweet, Darry. You're really sweet." You said grabbing his hand in return. You looked at the window and started to day dream a little as you stared at the stars.
"A real gentleman..."