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Genres/Tropes: Fake Dating (ish), Friends to Lovers, Oblivious!Klaine, College!Klaine, Fluff, Humor, Angst, Hurt/Comfort
Summary: Kurt Hummel is 21, in his last year as a Music major at NYU, and has never had his heart broken. When Taylor Swift announces the impending re-release of her Fearless album, Kurt seeks the help of his best friend to break his heart by April 9th.
A/N: I promise it’s not going to be as angsty as it sounds!!
Edit: umm that was a teensy lie???? It’s a LITTLE ANGSTY BUT YOU KNOW IT ALL WORKS OUT IT'S NOT THAT BAD I SWEAR
DOUBLE EDIT: this is THE stupidest and most self-indulgent thing I’ve ever written and i am not sorry
Kurt’s mother used to absolutely adore the Phil Collins version of You Can’t Hurry Love . The sound of it blasting through her car speakers as she dropped him off at school is practically etched into his memory, and by the first grade, he knew every single word by heart.
It’s a lovely sentiment and all, but after twenty-one years of a love life drier than the sahara desert, Kurt’s decided he will hurry love the hell up all he wants.
He remembers the day his dad and Carole got married, a light in his dad’s eyes that had never been there before. How lucky he must have been, to stumble across love like that not only once, but twice. Since then, Kurt Hummel has been ready to be in love, waiting patiently for his turn to arrive.
Despite having a front row seat to both Finn and Rachel’s devastation after their numerous fights and/or breakups, Kurt finds himself undeterred by the possible heartbreak he’d endure by falling in love. Isn’t that the point? If Kurt finds someone with the potential to break his heart, at this point, he’d consider himself lucky. He wants to be in love so bad that he’d risk replicating Rachel’s dramatic performance of The Only Exception, or adopting Finn’s tendency to kick chairs over.
But he’s not some deluded hopeless-romantic, either. Well, maybe he is a hopeless romantic, but he’s definitely a realist, too. He’s not asking the universe for much, just someone who he can share his life with. A friend he can stay with forever. He’s seen it with his parents, between his dad and Carole. It exists, he knows it.
Truly, he believes love can be as simple as that.
It leaves a dull ache in his life, feeling like he’s missing out on something that seems so universal. Tens upon thousands of love songs have been written, tens upon thousands of experiences, emotions, all expressing the same sentiment: finding love is worth the risk of losing it.
Tens upon thousands of love songs, billions of people in relationships, and Kurt has managed to stay single all his life. Some people like it that way, but not Kurt, who has seen The Titanic more times than he can count, and has read Pride and Prejudice so many times that he envisions himself finding his own Mr. Darcy (or perhaps his soulmate is closer to an Elizabeth in character).
Kurt loves his life, and his wonderful friends, and his amazing family, but wanting a boyfriend doesn’t make him any less grateful. It seems everyone else gets to experience relationships, why hasn’t he?
It’s been twenty-one years and the knowledge of his lack of romantic experience has always been there, niggling at the back of his mind. He’s had other things to focus on: mostly school and work whenever he had it. Normally he would just go about his life, keeping the tragically empty romantic aspect of it out of the forefront of his mind. Normally, he wouldn’t let this eat at him because what’s one more day after seven thousand. Normally, he wouldn’t care so much.
But Taylor Swift.
Taylor Swift is going to make Kurt Hummel lose his fucking mind.
Glee Headcanons That Follow Absolutely No Theme - Part Five
• Kurt's a dog person, and Blaine's a cat person. people always expect it to be the other way around, so everybody's always surprised when they find out.
• Mercedes has a very public crush on Niall Horan from One Direction. he kinda reminds her of Sam.
• Kurt refuses to play the Gay Best Friend, and his career suffered because of that, up until his breakout role. things went relatively smoothly after that.
• Marley's dream to become a singer took a while to finally come to fruition, but it eventually did when she was discovered by none other than Taylor Swift. she won Best New Artist at the Grammy's that very same year.
• Artie and Tina broke up, because they realized that they weren't really in love, but that they were both just scared that they wouldn't be able to find somebody else. they're still friends though, as it was a pretty amicable breakup.
• Tina still texts Mike every once in a while to say hello, and vice versa. they've briefly discussed the possibility of getting back together, but they decided against it, because they're both so busy.
• Brittany teaches dance classes to kids. they appreciate her strange sense of humor, and her ability to do the splits. because of course they do.
• Santana has had twitter beef with Demi Lovato.
• Quinn's celebrity crush is Taylor Swift.
• Jake and Marley eventually reconciled, but they didn't get back together. it never even came up, actually. Jake choreographs a lot of her music videos, and even has released a song with her when he got "famous enough" for Marley's label to allow it.
• there are recordings of practically every Glee performance, and Sancedes as a duo is a BIG fan favorite. when the videos were originally leaked, and Mercedes caught wind of how much everybody loved the pair, she flew Santana out to California so that they could perform a surprise rendition of River Deep, Mountain High at one of her concerts.
the 1: i think tina would sing this about mike at the end of season 6, after she proposed to him but before the five year time skip. (maybe she performs at a coffeeshop gig to make money during college?) it would be a reflection on their relationship, and how even though she’s happy with how her life is working out, she still would have loved to be with mike forever.
cardigan: i don’t know about timelines, but i want to hear marley singing this. she has such a lovely voice, strong but not overpowering in the way that some of the other female singers on the show could be, and i think she’d do a beautiful job with this song - especially the bridge!
the last great american dynasty: for some reason i can really see marley taking this one?? idk why but it just feels very fun and light, while also telling a really neat story at the same time, and i think marley would nail that balance. also, something about marley’s general vibe and vocals really reminds me of taylor - i think they both have a similar tone, sweet and simple and lovely - so i can definitely see her doing a rendition very similar to the original song.
exile: this is perfect for finchel around the breakup. they’d sing it as a duet, ofc, keeping the male/female parts the same as they are in the original song. i don’t have much to say about this, honestly - i feel like it’s a pretty obvious fit, and i think their voices would suit the song better than any other couple on the show.
my tears ricochet: this would be such a beautiful klaine duet set just after the breakup - maybe around thanksgiving? i think their voices go really well together (most of the time lolol) and i think kurt’s voice in particular would lend a super cool vibe to the songs.
mirrorball: i’ve seen people give santana this one, but this song just SCREAMS quinn to me. i envision her singing this either while she’s getting ready for prom (shot in the style of i feel pretty/unpretty) or while walking home after finn breaks up with her at jean’s funeral. to me, this song is about constantly putting on masks and doing things solely because it’ll help her keep finn, and thus her status and image. i think the lines “i’m still a believer, but i don’t know why/i’ve never been a natural, all i do is try, try, try/i’m still on that trapeze/i’m still trying everything to keep you looking at me” really fit quinn during late season 2 - she’s desperately trying to present herself as the perfect girlfriend, because she’s watching finn fall back in love with rachel and thinks that if she just tries hard enough, maybe she can keep him this time around.
seven: brittana duet alert! i’ve always headcanoned them as childhood best friends, and i can see them performing it in season one or very early season 2, reflecting on their early relationship and how it’s changed. it’d be a really sweet duet that would give their characters some backstory and grounding.
august: i think rachel would sing this after finn and quinn get back together during season 2. it’d be a classic rachel solo, the kind with super exaggerated emotions that make the rest of the glee club slightly uncomfortable.
this is me trying: this gives me such santana vibes. i think she’d knock this song out of the park, with a lovely mix of emotion and control, and i think it would have absolutely been one of the best solos on the show. it’s heartbreaking and she would really make it mean something, you know? i think it’d be gorgeous.
illicit affairs: while i didn’t like finn or fuinn, i think their one duet was really lovely, and i think this could have been a good song for them to pair up on around silly love songs - after they start their relationship, but before people start to find out about it. it’d be kind of like roots before branches in the sense that finn wouldn’t spit equal vocals with quinn, but would instead be more of backup for her. it’d play during a montage of them meeting up in empty classrooms and sending each other emotionally charged looks during glee club meetings, very classic secret relationship stuff.
invisible string: i think this could be a really lovely klaine duet!! again, a season 6 song, maybe during the wedding - it’s the story of how they feel like their romance was meant to be, and that “invisible string” of destiny is how they ended up overcoming all the obstacles to come back together.
mad woman: honestly give this to all the og glee girls towards the end of season 3 as one last hurrah before they head to nationals. i can see them doing it in the style of shake it out - all sitting on stools, with dramatic lighting, fierce outfits/makeup, and lots of complicated harmonies.
epiphany: i want to hear quinn and santana sing this song together. their one duet on the show (take my breath away) was absolutely gorgeous, with fantastic harmonies and a light, breathy quality that would suit this song incredibly well.
betty: another quinn song!! she’d sing this in season 3, after successfully talking rachel out of marrying finn (the car accident/baby stealing shit didn’t happen in this world, because those plots were stupid). she’d perform in front of the club, with backup from brittana, and she’d use it both to come out and to admit she has feelings for rachel - changing “james” to “quinn” ofc ;)
peace: this is a weird one, but stay with me on this - let puck sing this song. i feel like this song really sums up the crux of the problem that i have with quick - other than beth, they didn’t have much in common, and they were never able to give each other what they needed for a healthy, lasting relationship. however, i feel like puck would nail the emotional execution of this song. “would it be enough, if i could never give you peace?” is THE question that defines quick, and so i think puck would be the best fit for this song.
hoax: why am i getting brittany vibes from this? i mean, it’s a little profound for her, but i think she could sing this in early season 2, when she’s trying to convince santana to come out and be with her, before she and artie start dating. santana doesn't want to be with her openly, and brittany is hurt by that, but is still in love with and incredibly fond of her, so the song is about her clinging to santana even though she knows the relationship isn’t going to last unless santana is willing to go public.
the lakes: this was the trickiest song on the list for me, but i’m going to have to give it to quinn. quinn was very much set up as one of the smartest kids in glee club from an academic standpoint; she mentions being on honor roll in season 1, gets into yale, and tells rachel she had a straight A average while pregnant (which is literally SO impressive y’all), so it seems fitting to me that she would be the one to perform this song, which has very complicated, intellectual lyrics. she’d sing this in season 6 - and dedicate it to rachel of course.