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The Perfect Date

Summary:

Leo's first kiss philosophy: you need the right moment, the right timing, the right words, and the right atmosphere to make it one hundred percent perfect. This is how a normal boyfriend behaves and you're going to make this the best moment of your relationship thus far.

Casey's first kiss philosophy: kiss the dumb boyfriend. If he happens to turn his head, just don't say anything, because watching him pine over you while you're actively trying to solve his problem is more funny than just telling him to let you kiss him.

Chapter 1

Notes:

I made them kiss finally. If the cringe is too strong I apologize, but what good is it to live in fear of that which brings joy?

(See the end of the chapter for more notes.)

Chapter Text

Leo had to admit, the whole romance thing wasn’t as up his alley as he expected it to be. Out of the whole family, the skill seemed to come more naturally to Donnie than anyone, which was weird in its own right. Despite that bizarre and… frankly quite disturbing truth, there was one thing that Leo could take comfort in: Casey was just as bad as him at this crap. 

 

Leo had tried the whole suave, flirtatious act a few times, and had been met with nothing but a deadpan stare. Casey seemed to enjoy outright mockery a lot more than his flamboyant attempts at making her blush. Not that he was complaining. It seemed to come naturally to them.

 

So, gone were the bundles of flowers and abandoned were the cute coffee dates. It was the thrill of the chase for both of them, always looking for the next runner’s high. It worked for them. The chaos always had more of a place in their lives.

 

Unfortunately, the chaos had not yet landed Leo anything beyond a kiss on the cheek.

 

There was only so much he could handle. Casey was generous with the teasing and always up for a fight. It drove him wild in the best way, but there were only so many times they could get in each other’s faces before he started to desperately want to close that tiny gap and just kiss her. 

 

There were a few nights he was left laying awake, wondering if she had been trying to drop a hint. He really hoped he hadn’t missed some kind of cue, because this was getting ridiculous.

 

Leo would not have liked to know that he was somehow dodging Casey every single time she tried to kiss him. It was getting hard to keep track of all the times he had accidentally turned his head or moved completely out of her reach without even realizing it. She wasn’t sure how someone as smart as him could be the densest guy to ever exist, but here they were. She was half ready to give up and let him figure it out on his own. 

 

It wasn’t like she could do all that much about it. She had briefly considered grabbing him by the neck and just getting it over with, but even she wasn’t that blunt. As unconventional as they were, Leo seemed to want a certain precedent. She wanted to respect that.

 

That precedent was a date. Leo was sure of it. He just needed to set his plan in motion. 

 

As soon as the call picked up, Leo was talking. “Ceej! I have an idea for our next date.”

 

“What?”

 

“Trust me, it’s gonna be great.”

 

“Did you forget the skate park on Friday? I already bought soda and candy.”

 

“Not Friday. Our next next date.”

 

“Why on earth do we need to plan that far ahead?” 

 

Leo rolled onto his back, head lolling off the edge of his mattress. “Because I have the perfect plan for it.”

 

“What happened to playing it by ear?”

 

“Can’t a guy do something a little less spontaneous once in a while?”

 

Casey snorted. “Uh huh. Since when do you plan that far ahead for no reason? What are you up to?”

 

“Nothing just- just trust me, I think you’ll like it.”

 

“If it’s not laser tag I’m gonna be disappointed,” she warned.

 

“It’s not laser tag.”

 

“I’ve heard all I need to. It’s a no from me.”

 

“Okay, one: that was one of the worst Simon Cowell impressions you’ve done in a while. Two: would you give me a second to pitch the idea?”

 

“You’ve had a second! You keep on stopping and being cryptic instead of explaining!”

 

“Okay okay, you got me there. I was thinking we take a trip down to the hidden city, and I bring you to a really nice restaurant I found. Like black tie level nice. You can wear that dress you bought for the homecoming dance you and April never ended up going to.”

 

It sounded like she was looking for it already, clothes shuffling on the other end of the line. “Leo, that was like two years ago. I don’t even know if I still have that dress in my closet. I think I donated it back to the thrift store.”

 

“No way that’s your only dress.”

 

“I hope that was a joke, because otherwise you don’t know me that well.”

 

“What do you wear for formal events?”

 

“I don’t go to formal events. I think I have a decent pair of slacks and a button down if push comes to shove? I didn't think you were the fancy restaurant type.”

 

“I have my moments. If you can’t find something nice to wear we can scrap the idea.” That was not a sentence he wanted to come out of his mouth. He didn’t exactly have many other ideas.

 

“Hold up.” Casey’s phone thudded against the floor as she reached even further back into her closet. “Look at that! I still have it!”

 

“You’re really on board with the restaurant idea?”

 

Casey couldn’t drop the feeling that this was out of character for him, but she wasn’t above humoring him until she could find out what it was he actually wanted. “If you really want to, yeah, I’m on board.”

 

“Perfect!” It was more than perfect. He was going to make it the best date of her life. 

 

“You know, you could just tell me what it is you want. This feels like a cover for something.”

 

“What? Noooo.”

 

Well, if he had to be cryptic, at least he was keeping it under two weeks. It was better than not saying anything. “If you say so. I’ll see you Friday.”

 

“You’ll love it.”

 

“Sure, Leo.”

 

The planning helped. Leo couldn’t help but consider himself a genius. He didn’t feel nervous for their next date at all. He only had to worry about the next one. A whole month of being nervous and trying to find the right moment, and he was finally able to relax with her. 

 

Casey floundered with her board a little, still new to skating in the bowl. At least she hadn’t fallen yet. The last thing she needed was another skating concussion. She took a second to glance up at him. “You look good.”

 

“Of course I do.”

 

She rolled her eyes. “Not that. You’re not tense. You’ve been tense for a while.”

 

“Just… feeling good about next week.”

 

“Yeah, that big exciting date at a fancy restaurant you can’t afford?”

 

“We’ll just get the cheapest thing we can find.”

 

“You’re trying to starve me, aren’t you?”

 

Hey.”

 

“I mean, for all I know the past three years of friendship and couple months of dating were just an elaborate plan to finally get rid of me.”

 

Leo rolled his eyes, skating over to the half pipe while Casey gave up and went back for more taffy. She watched him skate up and down the sides, wracking her brain for hints. What was he up to? He was probably trying to build up to some grand gesture. Maybe he was finally wise to what she had been trying to do. Not that it was likely, but it was a nice thought anyway.

 

She turned her head at the sound of Leo’s cheering, just in time to see him doing a handstand on the edge of the pipe. He hadn’t been able to do that in a while. “I'm doing it!!! You seeing this, Case?”

 

“I hope you fall!”

 

“Only if you promise to kiss me better!” His stomach twisted a bit, but he kept the grin plastered on. Better she didn’t realize that wasn’t entirely a joke.

 

She pulled another taffy wrapper open while he leapt back down into the half pipe. In a moment he was by her side, hands digging into the grocery bag full of candy. He pulled out the gummy bears, popping a few into his mouth. “I can’t believe I pulled that off! Feels like my arms barely work most days!”

 

“Good job.”

 

“How do you feel about your progress? I saw you in the bowl, you look good.”

 

“Of course I do,” she chortled, mimicking him. 

 

“Yeah, yeah, use my words against me.” He held out the bag of gummy bears for her to take from. “At this point we’ll be on our a-game in no time. I’m almost fully recovered and you’re almost ready to learn how to do a kick flip.”

 

Then do we tell the guys I know how to skateboard now?”

 

“Right on the money! We’re gonna blow their minds, Ceej.” She tossed a wrapper at his face, but he caught it. “You’re on thin ice, you know that?”

 

“Oh yeah, what are you gonna do?”

 

“You don’t wanna know what I’ll do.”

 

“Ooh, scary. An empty threat.”

 

Leo rolled his eyes good naturedly, grabbing his soda. “I could always go play laser tag without you.”

 

“If you want to be single again, be my guest.”

 

“Wait, I’ve got a better one. How about I sign you up for one of Donnie’s experiments?”

 

Her eyes narrowed. “You wouldn’t.”

 

“Try me, twinkle toes.”

 

He should have known better than to set his soda down, because Casey tackled him in an instant. He keeled backwards, trying to keep his momentum and get the upper hand. He almost managed, able to loosen her grip a little and shove her halfway off.

 

She cackled wildly while they wrestled. “Take it back!”

 

He didn’t answer, just barely managing to flip them over while Casey squawked. She weaseled a leg underneath him and kicked, sending him tumbling off.

 

Before she could get up, he had stood and bolted, and she was more than happy to chase him down. She couldn’t stop laughing. Leo’s own laughter rang in her ears. 

 

By the time she caught up they were both nearly out of breath. She leapt onto his back and locked him in a chokehold. Not to be outdone, Leo flipped her onto her back, standing over her. “I take it back. You happy?”

 

She swept his legs out from under him, and he slammed into the concrete. Casey’s grin was wild, sparks flying off of her while she howled with laughter. 

 

Oh she was in for it. “You think you’re funny!”

 

She shrieked as he grabbed her, laughter only getting louder as Leo dragged her close. She was laughing too hard to fight back. Her hands weakly gripped the collar of his sweatshirt, doing nothing to get him off balance.

 

Leo’s heart soared. Her face was scrunched up, eyes barely open, laugh sounding more like a hyena than a human. To put it into proper words, she was perfect. 

 

She was more than perfect. Casey was everything.

 

He didn’t let go, even as she threatened to start another wrestling match between wheezes. He just soaked in the sight of her as she finally ran out of breath. Before she could open her mouth to tease him again, he kissed her.

 

Their lips parted with a quiet smack, and Casey’s eyes went wide. Leo stared back, still trying to register what he had just done.

 

“What?”

 

Oh no. “I…”

 

She sat up, a smile tugging at the corners of her mouth. “I thought you were planning on doing that next week! Isn’t that what the whole fancy dinner was going to be for?”

 

The words hit him like a brick wall. “…I have not been hiding this very well.”

 

“Not even close.”

 

“Wait, if I’ve been that obvious, how come you didn’t do anything? Or- I don’t know, mention it?”

 

Casey leaned down and kissed him again, laughter buzzing against his lips. “I have been doing something.”

 

“You’re lying.”

 

“I’ve been trying to kiss you for weeks.”

 

He sat up the rest of the way, stomach sinking. “You’re lying.”

 

“You kept dodging me.”

 

“Are you kidding me?” 

 

“No!”

 

He groaned, sinking into his shell while Cass went back to cackling like a hyena. “All those times you kissed me on the cheek?”

 

“About half of those.”

 

Nooooo…

 

“You got there!”

 

His face burned red. “Yeah, after like- a month!”

 

“You’re okay, you big baby.”

 

“I wish you would have said something.”

 

“Hey, don’t say that. I knew you didn’t want me to.”

 

He ran the scenario in his head. It didn’t feel as satisfying. “Okay, maybe not, but just… ugh, I’m so stupid.”

 

“It’s a good thing I don’t like you for your brains.”

 

Hey.

 

She kissed him again to keep him from whining, then stood up and walked back to the candy. A group of teenagers was starting to come to the skatepark. It was almost midnight, and she’d rather die than have to fight for the candy she bought. 

 

Leo chased after her, helping gather their stuff. With the boxes and bags of candy sealed and the soda bottles chugged to the last drop, they were ready to head back.

 

Leo shouldered the candy. “So… dinner’s off?”

 

“Up to you.”

 

“I mean, it’s not really our style so… it’s off.”

 

“Thank goodness. I was not interested in a tiny portion of gourmet tentacle or whatever they serve at that place you found.”

 

“In hindsight I may have gotten a little overexcited.”

 

“So what made you do it today?”

 

The question caught him off balance. She could tell by the way he stared blankly into the distance that it wasn’t where he was expecting the conversation to go. He fumbled with his words for a minute, trying to put his thoughts together.

 

“Honestly? I… you looked ridiculous.”

 

She stared at him flatly. “Way to make a girl swoon.”

 

“You suck, that’s not what I meant,” he chuckled. “You were just laughing, and I was looking at you, and… I remembered why I love you so much in the first place.”

 

“You’re being cheesy.”

 

“The truth is cheesy, Cassandra Jones. If you don’t want the dairy, ask me to lie.”

 

“Oh my gosh.”

 

“Also, for someone so afraid of being cheesy, you sure do stick to a script!” He shot. “Since when has The Casey Jones Senior waited to do what she wants? I’m surprised you didn’t grab me by the throat just to get it over with.”

 

“Don’t turn this on me!” She shot back. “You wouldn’t have wanted that, I’m not the cheeseball for playing the game you want me to.”

 

“You so are! You waited because you love me and you can’t stand to see me disappointed.”

 

“So what if I do?”

 

“I’m just saying, sometimes we pull off the whole ‘romantic’ shtick pretty good.”

 

“Romantic enough for laser tag?”

 

Leo glared at her. “Fine. But only if we pick opposite teams and get to throw in a forbidden love b-plot for dramatic effect.”

 

“You’re such a theater kid.”

 

“I am not!”

 

While he protested, Casey grabbed the bag of candy from him and climbed the rickety fire escape to her window. Leo simmered down enough to help her pry the sucker open a bit more and toss the candy in. 

 

Before she climbed all the way in, she gave Leo an expectant look. He didn’t register it.

 

“Man, you really are dense.”

 

Is that what that was supposed to mean??? I thought you looked at me like that when you wanted to fight me!”

 

“They’re the same look. The gamble makes it fun.”

 

Leo rolled his eyes. One last kiss for the night and he was gone. He really did take his sweet time getting that milestone over with.

 

It wasn’t all bad though. She had her own payback, in the form of black lipstick now stuck to his face. She probably should have said something, but he would find out eventually. She’d get a good laugh out of it too.

Notes:

My friend who I am slowly getting into rottmnt was very angry that the last three leocass fics did not make them kiss. This is a formal apology to her and anyone else who has been disappointed by my previous leocass fics. They kissed.