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No One Can Escape Gossip, Not Even The Greasers by keylime2001
Fandoms: The Outsiders - S. E. Hinton, The Outsiders (1983), The Outsiders: The Musical - Jamestown Revival & Levine/Rapp, Gossip Girl (TV 2007)
03 Nov 2025
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In 2007, Ponyboy Curtis got a scholarship to a private school in NYC. So the Tulsa gang uproots their lives and moves there. Takes place after The Outsiders by S. E. Hinton. Dally and Johnny are still alive. The gang doesn't know that they will be thrown in a different sort of social warfare.
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pride and mostly pretense by letterstomy_lqver
Fandoms: Gossip Girl (TV 2007), Gossip Girl (TV 2007) RPF
31 Oct 2025
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blair waldorf’s return to new york was only supposed to involve couture, cocktails, and a firm no to her mother’s parade of dull suitors. but when social obligation threatens her carefully maintained indifference and everything she's worked for to find some stability in life, she does what any rational woman would do—concoct a scheme, in hopes that it would shut the mouths of all who judged her.
dan humphrey was riding a bit of a dry spell—writing here & there, attending the right parties, staying relevant in new york’s literary circuit to keep the wolves at bay. but the usual slog of dodging pretentious critics and feigning interest in highbrow nonsense wasn’t exactly thrilling. then came arthur pembroke’s cutting words: a challenge thinly veiled as a compliment. and suddenly, he had a new story to write: to shake off the slump, land the coveted fellowship, and prove the naysayers spectacularly wrong.
the terms are simple: smile for the cameras, look like they like each other, and absolutely NO catching feelings. that was easy enough for two people who passionately disliked each other, right?
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Chuck and Jenny, left alone in New York after graduation, find themselves entangled in a deeply passionate friends with benefits arrangement. What happens when Chuck's circumstances change overnight and he finds himself needing more from Jenny than he anticipated? Chuck and Jenny have both changed and grown up since highschool but can a leopard really change its spots? Can they survive the Upper East Side? Can they survive the demons of their past and make it, against all odds?
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Confessions of a Runaway Debutante by Stapler_Stealer
Fandoms: Gossip Girl (TV 2007), Bridgerton (TV)
24 Oct 2025
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“Is this some poorly disguised attempt at courtship?” Blair casts her most condescending look upon him. “If it is, I beseech you to desist at once, for I do not associate with the likes of you — namely, boys with…ridiculous hair, dubious lineages and laughably enormous egos.”
He blinks back in stunned silence at the bluntness of her words — but not for long.
“I do not happen to be looking for a wife, but even if I were — ” the curly-haired heathen scoffs. “I’d surely court a lady with a far more…pleasant disposition.”
(Bridgerton Dair AU: Desperate to escape her impending engagement with Charles Bass, the Duke of Sussex — Blair Waldorf will stop at nothing. Even if it means hunting down the secret identity of London’s most enigmatic writer — the infamous Lady Whistledown herself.)
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Jenny and Nate run into each other on a snowy December day, and through ice skating and dinner find themselves ready for something old.
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Jenny thought she’d left the scandals and secrets of the Upper East Side behind. But when she’s drawn back into Manhattan’s glittering world of power and privilege, old temptations resurface.
As mysterious tips from an anonymous sender begin to appear, Jenny finds herself unraveling a web of secrets tied to the Metropolitan Elite. At the center of it all is a question that could shatter their carefully curated lives: Who was Bart Bass, really?
A Jenny Humphrey redemption arc. Season 4 AU, loosely follows canonic events but ultimately very different [JH/CB]
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good morning upper east- I mean, Ao3 reader, hope you enjoy this first chapter of a looong fic
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Then maybe he wouldn’t be here— in a tiny hotel room lookalike that smells like antiseptic, with two fading lines on his wrist, and a sister who feels burdened to come back to New York for him.
Because isn’t that what he is?
A burden.___
Gossip girl in Eric’s pov/ gossip girl rewrite
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au: dan humphrey is randomly paired with nate archibald to room with in college. nate never seems to be around for the first few weeks until dan walks in on him and his fiancee, blair waldorf. dan's quiet life of studying and skyping with vanessa quickly turns into a life full of more drama than he bargained for
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[Based on Season 4 ep 17 and beyond]
Dan and Blair have hated each other since the day they met, but after one kiss both of them begin to question if whether it was really hate they were feeling.
Dan decides he's going to give himself a chance and start to pursue Blair except he now has to fight for her love against Chuck and Louis.
Blair has to decide if she should listen to her heart or her head, but how can she choose when all three suitors are competing fiercely for her love? All while she tried to maintain her crumbling friendship with her best friend, Serena, Dan's ex.
[Louis storyline modified and cousin Charlie is actually cousin Charlie not Ivy]
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Daniel Humphrey was many things; a writer, a lover, thin, a caffeine addict, an appreciator of the arts— but especially transgender.
Extremely, actually.
But he didn’t always know that— or he didn’t want to.
- Language:
 - English
 - Words:
 - 1,162
 - Chapters:
 - 1/?
 - Kudos:
 - 8
 - Hits:
 - 107
 
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Blair doesn't confide in Nate about the hotel instead she talks to Dan, AU and Cannon-divergent from there.
Blair did get into Yale and chooses to work on herself wanting someday to deserve a love like Dorota and Vanya.
Dan can't help but constantly be impressed by her and it inspires him to write "Inside" earlier but instead of going to Georgina or Vanessa he asks Blair to read and edit it for him, wanting her approval before he tries to publish it.
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After Chuck takes advantage of her and Blair tells her to leave the city, Jenny takes more drastic measures.
Nate isn't going to let her slip away.
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Jenny wants to design, Nate's trapped in politics, but their summer internship at a Manhattan magazine becomes something neither expected, champagne-fueled confessions, late-night collaborations, and a love story written between deadlines.
Series
- Part 24 of AU-August 2025
 
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You (Audrey Van Allen) are a queen at your private academy in Seattle, living like royalty. That was all up until your parents decided to move to New York, specifcally the Upper East Side of Manhattan. You take it as your duty to do all you can to make sure you can rebuild yourself back into royalty.
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After a student has an accident that causes Chuck, Nate, Serena and Blair to come up with a plan on how to save their reputations and there is only one person smart enough to help them.
When Dan finds out the truth he helps his boyfriend and his friends snd makes sure that they don't get into trouble.
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every time we fight (i forget who's winning) by OnceUponaSwanQueen
Fandoms: Gossip Girl (TV 2007)
15 Aug 2025
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Blair Waldorf had senior year perfectly planned until Dan Humphrey took control of St. Jude’s War Games team. Now he’s not just challenging her crown, he’s getting under her skin. Strategy, sabotage, and something dangerously close to love.
Series
- Part 16 of AU-August 2025
 
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He finally had the father—some semblance of the family—he’d always wanted.
How could everything be falling apart?
Set within Season 3. Story begins right after Episode 19, “Dr. Estrangeloved.”
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This story reimagines the untold love story of Lily and Rufus from Gossip Girl, delving into their past and offering a satisfying resolution to their journey. Through a mix of original storytelling and canon-inspired moments, it explores how Lily and Rufus first met, the challenges they faced in their youth, and the enduring connection that defined their relationship.
By focusing on Lily and Rufus’ perspectives, this story brings to life the nuances of their history and offers an alternate ending, one that reflects the love, growth, and chemistry they truly deserve.
For fans of Gossip Girl who always wished for more Lily and Rufus content, this is a heartfelt tribute to their relationship and a vision of how things should have been.
 
