Chapter 6: Gossip Girl Fanfiction - Chapter 6: The Handmaiden's Tale
"Behind every mask lies a secret, and in the Upper East Side, secrets are the most valuable currency. So when the elite throw a masquerade ball, you can be sure the biggest revelation won't be who's behind the mask—but who gets unmasked. XOXO, Gossip Girl."
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Morning at Jain Capital – The Art of Anticipation
Every morning before school, I spent an hour at Jain Capital. My father thought I was just taking an interest in the family business, but in reality, I was shaping its future.
Today, I was reviewing a potential investment in an emerging digital advertising firm. Right now, nobody was betting big on digital. They were stuck in traditional media—TV, magazines, billboards. But I knew better. In a few years, digital advertising would dominate, and companies like this one would be sitting on an empire.
My assistant knocked and entered. "Sir, your car is ready."
I nodded, closing my laptop. Time to switch gears.
Because tonight was the highly anticipated Masquerade Ball.
And in our world, masks didn't just hide faces. They revealed truths.
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The Masquerade Ball – Where the Games Begin
The Van der Woodsens were hosting the Masquerade Ball, and everyone who mattered was going to be there. A night of glamour, secrets, and, of course, Gossip Girl watching our every move.
When I arrived, The Palace was transformed—soft golden lighting, chandeliers reflecting off crystal glasses, masked figures moving through the ballroom like a scene from a classic film.
Chuck, ever the opportunist, was already surveying the crowd.
"Bass," I greeted.
He smirked. "Jain. Ready for a night of mischief?"
I grabbed a drink from a passing waiter. "Always."
Nate joined us, adjusting his mask. He looked tense. No doubt his family issues were weighing on him.
Chuck leaned in. "Tell me, who are you betting on for tonight's biggest scandal?"
I scanned the room. Serena and Dan were here—an unlikely pairing that was still defying expectations. Blair was somewhere in the mix, undoubtedly plotting something. And then there was Jenny Humphrey, once again out of her depth but desperate to prove otherwise.
I smirked. "Give it a few hours. The masks will come off, one way or another."
Chuck grinned. "Now that's the spirit."
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Blair's Plan – A Cinderella Trap
Blair had her own agenda for the night. She was setting up Nate to unknowingly dance with Jenny, the "mystery girl," hoping it would lead to humiliation when he found out. Classic Blair—calculated, ruthless, and always playing three moves ahead.
When I found her standing by the balcony, sipping champagne, I knew she was already enjoying her work.
"Having fun?" I asked, leaning on the railing beside her.
Blair smiled, but it didn't quite reach her eyes. "Oh, you know me, Aryan. I thrive in nights like these."
I raised an eyebrow. "That why you're orchestrating a masquerade of your own?"
She turned to face me fully. "And what exactly are you implying?"
I took a sip of my drink. "That you don't leave things to chance. Ever."
Blair's smirk widened. "Then you should enjoy the show."
I glanced toward the dance floor, where Nate—oblivious—was already dancing with Jenny. Blair had executed the setup perfectly. The question was, would it end the way she wanted?
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Jenny's Big Moment – And the Aftermath
Jenny thought she was living her Cinderella fantasy—dancing with Nate, lost in the magic of the night. But in our world, fairy tales didn't come true. They shattered.
When the clock struck midnight (or rather, when the masks came off), Nate's reaction was instant. Confusion. Realization. And then, disappointment.
Jenny's heart sank. Blair's plan had worked.
But what Blair didn't expect was Nate's reaction. Instead of getting angry or cruel, he simply walked away, leaving Jenny standing there, humiliated but not destroyed.
I watched from a distance. Jenny was learning—slowly. But she wasn't broken yet.
Blair, however, was less than thrilled.
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Serena and Dan – A Different Kind of Game
Meanwhile, Serena and Dan were navigating their own set of complications.
I caught a glimpse of them sneaking away from the crowd, finding a private corner on the terrace. Dan, ever the Brooklyn romantic, was trying to make sense of this world. Serena, caught between who she was and who she used to be, was trying to hold onto something real.
Chuck, of course, had no patience for their love story.
"Let me guess," he said, joining me at the bar. "Brooklyn Boy is trying to keep up."
I smirked. "He's doing better than expected."
Chuck scoffed. "For now."
That was the thing about Dan. He was stubborn. But this world had a way of wearing people down.
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A Private Conversation – Nate's Doubts
Later that night, I found Nate sitting alone in the lounge, drink in hand, mask discarded beside him.
"You look like a guy who just realized he's a pawn in someone else's game," I said, sitting across from him.
Nate exhaled. "Blair set me up."
I nodded. "You surprised?"
He chuckled bitterly. "No. I just… I don't know if I can keep doing this."
I studied him. Nate had always been caught between expectation and desire—between what his family wanted and what he actually wanted.
"You don't have to play by their rules," I said.
He looked at me, skeptical. "Says the guy who plays them better than anyone?"
I smirked. "I pick which rules to follow. You should try it sometime."
Nate sighed. "Yeah. Maybe I should."
It was just a conversation. But I could tell something in him was shifting.
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Final Gossip Girl Blast
"Masks may have been worn, but the truth always finds a way to slip through the cracks. Betrayals, heartbreaks, and one Little J learning that in our world, nothing is ever what it seems. Sleep tight, Upper East Siders. You know you love me. XOXO, Gossip Girl."
I checked my phone and smirked.
The night had delivered.
And I had a feeling the fallout was just beginning.