The Outsiders Headcannons

(Requested) The Waitress - Darry

"Okay, I'm taking you all out for dinner tonight." Darry announced, freshly changed from his work uniform and into clean clothes.
     "Where to?" Pony asked, he seemed to be the only one not busy celebrating quite yet.
     A pained smile crossed Darry's face, "Just the Dingo, so don't get too excited."
     Somehow that seemed to relieve Ponyboy. At least there wouldn't be any socs to rough them up.
     Half an hour later, the group arrived at the diner. It wasn't much, and it was a little shady. But it was the Dingo.
     "Darry, if you're paying, that means I can order whatever I want, right?" Asked Dally with a smirk playing on his lips.
     "Don't make me regret this."
     "Mhm."
     When the waitress came, she was beautiful. Really, one of the much prettier greaser girls.     "Hi, I'm Y/n, I'll be your server today. Has everyone decided what they want?" She asked with a cheery but tired smile.
     "I know I certainly have," Dally leaned back in his seat to eye her up and down, "You."
     Rather than a blush and giggle, she gave a fake smile, saying, "Anything on the menu, sir?"
     This time it was Two-bit who spoke up, "if I write your name down on the menu, does that count?"
    "Haha," She said, "does anyone have a real order to make?"
     "Hey, uh, what's the special ingredient in the milkshakes? Cause if you let me take you out, I can show you." Steve winked, which caused Soda to laugh. "Sorry sweetheart. By the way, is that what you'd like me to call you in bed tonight?" When Soda spoke, everyone expected her to swoon.
     She didn't.
     Johnny and Ponyboy sank further down in their seats. And partly as a result of that, and for his own embarrassment, Darry finally spoke up. "I'm really sorry about," He gestured to everyone seated. "Well, all of them. As for our orders, we'll just be taking three burgers and fries, two chocolate milkshakes and one vanilla."
     This time, her smile was genuine. "Is that all?"
     He glanced over at their mortified faces with a grin, "Yep, that'll be all, thanks."
     With his jaw to the floor, Soda asked, "Dar-bear, just to be clear, the other two meals are for me and Pony, right? Your brothers?"
     "Nope, Johnny and Pony because they respect women."
     "Wha- I don't disrespect them!"
     He quirked an eyebrow.
     "You know what I mean," Soda slumped back in his seat.
     After finishing their meals, which Darry later felt bad about and bought for everybody else as well, he told the gang, "Why don't you all go on home. I'll meet you there."
     After the last pair of feet left the door, he walked up to the counter, where're the pretty young waitress stood.
     "Hey, uh, I'm real sorry for all that back there," He spoke with a somewhat nervous grin.
     She smiled, jeez she had a pretty smile, "hey, it's alright. Thanks for defending me back there."
     "Is that what I did?"
     "That's how I took it?"
     "Then I did defend you."
     She bit her lip, "Can I have your number? Uh, just so I can call you to defend me if something like that happens again."
    He laughed. Darry laughed. Ponyboy would've been awestruck if he had witnessed it. "Sure," he scrawled it down on the notepad she handed him. "I'll see you around."
     It took one hour after he got home for her to call. "Hello?"
     "Hi, um, this is the Curtis residence, right?"
     "It is."
     "Is this Darrel Curtis?"
     "It is. You can just call me Darry, by the way."
     "Oh! Um, yeah. Haha. This is y/n, from the diner."
     "I remember you."
     "I was just wondering if you maybe wanted to hang out sometime."
     "I'd love to. When?"
     "How 'bout tomorrow night?"
     "Sure, I'll swing by the diner at eight?"
     "Great!"
     After hanging up the phone he announced, "I have a date."
     And three dates later, he was walking her home. This pretty, funny, smart waitress had Darry wrapped around her finger.
     They stood on her doorstep, holding hands for a long moment. "So um, I'll see you later, yeah?"
     "Yeah," he breathed out.
     When she turned to open the door, he gently tugged on her wrist to pull her back to him.
     "Just one more thing," he meant down with blue-green eyes flickering closed, and he kissed her. Gently, softly. On her doorstep until finally, they pulled apart.
     The boys never stopped teasing him about his pretty new girlfriend.