So this is actually only based off the description in the prompt, as I've never seen either of those movies. Sorry!
"Bro. C'mon. Please!"
"No," Kurt replied, not looking up from his book.
"But this show's only in Columbus for two weeks!" Finn said, hands clasped under his chin in a pleading gesture. "If I don't ask Rachel soon, Jesse will, and then it's game over. Please, just ask someone, anyone out so Mom and Burt will let me date Rachel."
"What part of no didn't you understand, Finn?" Kurt asked, shooting Finn an icy glare. "I'm sorry that Dad and Carole said you can't date before college unless I do too, but there are plenty of fish in the sea! Rachel and Jesse probably won't last forever, either."
"You don't get it! Rachel makes me feel like I can succeed outside of Lima, like I'm worth more than my football jersey. If you'd ever had feelings for someone, you'd know."
Kurt flushed bright red involuntarily at Finn's last remark, and unfortunately for him, Finn noticed.
"You do have a crush on someone!" Finn said triumphantly. "Who is it? I can totally butter them up for you."
"No!" Kurt said, trying to hide behind his book again. "You can't. Probably no one can."
"Why, who is it?" Finn asked, pulling Kurt's book away and dropping it to the ground. He plopped onto Kurt's bed next to him, making Kurt bounce a few inches in the air.
Kurt mumbled indistinctly.
"Who?"
"Blaine Anderson, okay?" Kurt said loudly, knowing Finn wouldn't give up until he got an answer. "I like Blaine, so I'm sorry, but you're gonna have to hold off on girls until college. There's no way he'll ever give me the time of day."
"You're really into Blaine? But he's so..," Finn trailed off before shrugging and saying, "scary, I guess."
"I know he looks tough, but I've seen him help Ms. Pillsbury rearrange her pamphlets after she dropped them all in the hallway, and she didn't even ask. He also ended up sitting in Azimio's seat in Trig when he was out sick one day, so now I don't get spitballs shot at the back of my neck all the time," Kurt said, staring at his pants intently. "Plus he's, you know, smoking hot."
"Bro!"
"You once treated me to a ten minute monologue about Rachel's butt," Kurt said. "You can handle me saying a guy is hot."
"Fine, fine," Finn said, relaxing. "And I guess I see it. You know, he kinda looks like Rach-"
"Finish that sentence and I snap all your drumsticks in half," Kurt warned. "There are some images I don't need, Finn!"
"Fair enough. But don't write yourself off just yet, bro. I think we know someone who can help you out," Finn said, getting a sly smile on his face.
"Wha - who?"
"I need to ask them first. We're gonna get you your man, Kurt!" Finn said excitedly. He sprung off Kurt's bed and quickly left the room, leaving Kurt blinking in confusion in his wake.
"Oh, I am not looking forward to this," he muttered, leaning over to grab his book off the floor. Unbidden, a daydream of Blaine picking him up for a date one evening came into Kurt's mind, complete with flowers in Blaine's hand and a bright smile on his face.
"Don't be silly," Kurt told himself, smoothing out the wrinkled pages in his lap. "You'll be lucky if Blaine doesn't laugh in your face after whatever Finn's planning comes to fruition. Just accept that there are no guys in your league in Lima, Hummel."
All the stubborn wake-up calls in the world couldn't keep Kurt from imagining that the sweater he was wearing was actually Blaine's leather jacket, though.
"I heard you need my help."
"Jesus!" Kurt jumped and turned around at his locker, revealing Quinn's familiar smirk and shock of pink hair. "What are you talking about?"
"My illustrious ex-boyfriend told me about your crush," Quinn said, leaning against the neighboring lockers. "Thought I might have some ideas for getting Anderson to notice you."
"I'm gonna kill him."
"While Anderson might notice you getting cuffed and sent to juvie for murder, that won't get you any closer to him," Quinn said, eyes sparkling merrily. "Or did you mean you wanted to kill him? Because that also seems a bit counterproductive."
"Cut the crap, Quinn," Kurt said fiercely. "I don't know why you'd want to help me or Finn out, but it's fine. Finn will just have to find another Rachel in college."
"I want to help because it's my fault Finn's even got to follow this rule in the first place," Quinn said, soft and serious. She straightened up, looking Kurt dead in the eye as she continued, "If I'd just been honest about Beth's father, your parents never would've stopped trusting him. But I was stubborn and naive and thought we could be a little family of our own, and now my parents think I'm worthless, Beth's been adopted by someone I'll never meet, and Finn can't date the girl he's actually crazy about. If getting you a date with Anderson will help me make it up to Finn, then I'll do it. Plus…."
"Plus?" Kurt asked, a little skeptically.
"Word around the Skanks is Blaine's had his eye on a certain nerd for a while now," Quinn said, smirk reappearing ever so slightly. "Maybe if we give him a little more to take a look at, magic will happen."
Kurt just gaped, unable to process this news.
"I'll be at your house after school today. Be ready for the makeover of your life," Quinn warned, starting to walk away. She only made it a few steps before Kurt reached out and stopped her.
"Just so you know, Finn doesn't blame you for not being able to date. It was his choice to go along with your story, and he's accepted the consequences," Kurt said quietly. "If you still want to help me, I - I think I'd like that, but don't do it out of misguided obligation."
Quinn bit her lip before giving Kurt a tiny, sincere smile. "Like I'd give up the chance to make Anderson's mind explode when he sees you. But...thank you, Kurt."
Kurt smiled back and let her go.
"Looking good, bro!" Finn said as they were walking into McKinley the next day.
Kurt choked out a thank you, suddenly very nervous about what Blaine would think. Quinn's makeover was, well….
"My work here is done," she'd said, spinning his chair around so he could see in his bathroom mirror.
"Holy shit," he'd said, jaw hanging open as he took in his new, upswept hairdo and the hint of eyeliner she'd applied. Paired with the ripped t-shirt, tight jeans, and studded black boots she'd made him buy at the thrift store, it made him look almost...dangerous.
"Name your first kid after me. Quinn's unisex, it'll work no matter what!" Quinn had chirped, and that was that.
"I got this," Kurt whispered, trying to work up some courage. "I can do this."
"Hell yeah!" Finn said at a normal volume, apparently overhearing Kurt's pep talk. "Go get 'em."
He slapped Kurt on the shoulder encouragingly as they entered the building, then turned off toward his own locker, leaving Kurt to face the hordes alone. Kurt squared his shoulders and started walking, hoping for the best.
"Whoa."
"Is that-"
"Fuck me sideways. Hummel?"
"That's my name," Kurt replied sassily, feeling emboldened by the look on Blaine's face. "You need something?"
"Your number," Blaine said, shooting Kurt a cocky, handsome smile.
"You really think that's all it'll take? Impress me, Anderson. Then we can talk," Kurt said, sauntering away. He quickly replayed the conversation over and over in his head, looking for anything potentially embarrassing, but before he could overanalyze it, Quinn materialized by his side.
"He's still standing where you left him, and I'm pretty sure he was staring at your ass the whole time as you walked away. You've got game, Hummel," she said impressedly.
"Let's hope I can keep it up," Kurt replied.
"Ack!"
"Surprise," Blaine said, smiling winningly and gesturing toward the empty classroom he'd pulled Kurt into. "Our lunch awaits."
"Is that-" Kurt began, smelling the scent of warm bread and tomato sauce.
"Breadsticks and pasta from Breadstix? Yep," Blaine finished. "Your brother told me what you liked - I hope he wasn't mistaken."
Kurt smiled at the brief flash of awkwardness from Blaine. "He's right. It smells delicious, Blaine, how-"
"I may have cut third period," Blaine said with a wink. "Who needs to know how to play dodgeball, though?"
"Hasn't come in handy yet for me," Kurt said, moving over to a chair.
"Hey!" Blaine said, motioning for Kurt to stop before going over and pulling out the chair for him. "I wasn't raised in a barn."
"You're starting to impress me," Kurt said, smirking at Blaine as he took his own seat. "Keep it up, and you might just get my number by the end of the day."
"Oh, baby. You ain't seen nothing yet," Blaine said, making Kurt shiver. He started serving the food, keeping up their banter as he did, and before Kurt knew it, the end of lunch bell was ringing and Blaine was escorting him to AP World History.
"Blaine?"
"Yeah?" Blaine said, tightening his grip around Kurt's waist a little as he smiled up at him.
"Meet me after school. I think you might need my number so you can call me once you get home."
The genuinely excited smile on Blaine's face made Kurt's heart start pounding in his chest.
"Over here!"
"Miss me, handsome?" Kurt cooed, walking over to Blaine's motorcycle.
"Every second," Blaine said, smug grin on his face. "I was thinking that maybe I could give you a lift home, get your address and your number at the same time. I want to know where to pick you up on Friday, after all."
Kurt's jaw dropped as he realized that Finn's plan and Quinn's makeover had actually worked so well that Blaine asked him out, not the other way around.
"Climb aboard, gorgeous," Blaine said, patting the space behind him on the bike.
Suddenly, Kurt was frozen for another reason - fear.
"I - I'm sorry, I can't-"
"Am I moving too fast? I'm sorry, I thought-" Blaine began, all cockiness gone. His eyes were big and worried,
"No! No, I want to, I just - motorcycles kind of terrify me," Kurt said, finding his voice again. "My dad's taken apart so many totaled bikes for parts, and we passed this accident once that - ugh. I'm so sorry, I knew you probably thought I was some kind of badass after seeing me today, but I really can't, Blaine. If this is a dealbreaker, I get it."
"Kurt," Blaine said softly, getting off the bike to stand by Kurt and place a gentle hand on his arm. "Don't you get it? I want to go out with you, not your clothing. I might have found it easier to talk to you today, but I like you no matter what you're wearing."
"So if I want to go back to my normal style tomorrow?" Kurt asked shyly.
"Then I'm looking forward to seeing if your sweaters are really as soft as they look - if you're okay with me touching you, that is!" Blaine said, looking a bit panicked.
"I may have been a little bolder today, but we didn't do anything I didn't want to," Kurt said, making sure to look Blaine in the eyes as he spoke. "I'd love to go out with you on Friday, too - but maybe in a real car?"
"Whatever you want," Blaine promised. He leaned in, but a tall figure in Kurt's peripheral vision made him stop Blaine for a moment.
"Just a sec. It's important, I swear," Kurt said softly before turning to yell, "Finn! Go secure your weekend plans!"
Finn whooped and ran off while Kurt turned back to Blaine and initiated the kiss Blaine had been going after, laughing slightly into Blaine's mouth as he took in Blaine's confused expression.
"I'll explain later," Kurt said when they broke apart. "Right now, I'd like to keep kissing my weekend plans, if that's alright."
"No complaints here."
Kurt probably could've kept kissing Blaine forever, but Finn was back all too soon and begging to go home so he could finally get permission to go out with Rachel. Kurt eventually obliged - but only after he wheedled Blaine's leather jacket out of him as proof for their parents.
(If Blaine's reaction to him wearing the jacket over his softest cardigan the next day was anything to go by, Kurt might get to keep the jacket as long as he liked. He figured Blaine might get it back before Rachel ever returned Finn's football hoodie, at least.)