Chapter 3: Gossip Girl Fanfiction - Chapter 3: Poison Ivy
"Spotted: Upper East Siders trading their designer bags for college brochures. That's right, darlings—it's Ivy Week, where futures are decided and reputations are made. But be careful, one wrong move and your dreams could go up in flames. XOXO, Gossip Girl."
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St. Jude's & Constance Billard – Ivy Week Begins
Ivy Week was the time when every elite family in Manhattan flexed their influence. Colleges sent representatives, and students fought for the coveted honor of being their school's face. For people like Blair, it was a stepping stone to Yale. For Nate, it was his father's expectation. For Chuck, it was a joke.
For me? It was a formality.
I already knew where I'd go if I chose college. But for now, I was more interested in watching the others scramble.
At St. Jude's, Chuck, Nate, and I sat through the orientation speech, delivered by a polished Princeton rep.
Chuck smirked. "Who actually takes this seriously?"
Nate sighed. "Maybe people who don't have their future handed to them?"
I chuckled. "And here I thought you loved having your life planned out."
He shot me a look. "Says the guy who has more money than half of New York combined."
Fair point. But unlike Nate, I wasn't being forced into a legacy I didn't want. I was creating my own.
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Dan's Opportunity
At Constance, Blair and Serena were circling each other like rivals on a battlefield. But the real wildcard was Dan Humphrey.
When Headmistress Queller announced that one student from St. Jude's or Constance would have their essay published in The New Yorker, Dan's entire world shifted. This was his shot.
Later, in the courtyard, I found him staring at his notebook like it held the secret to the universe.
"You planning on writing your way into Harvard?" I asked.
Dan looked up, startled. "It's for The New Yorker."
I nodded. "Big deal for you."
"It is," he admitted. "This could change everything."
I studied him for a moment. Dan wasn't part of our world, but he wanted to be something. He wasn't like Chuck or Nate, born into power. He was trying to carve his way in.
"You'll do fine," I said, before walking off.
Dan didn't realize it yet, but he had more potential than he gave himself credit for.
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Blair vs. Serena – The War Continues
At the Ivy Week cocktail event, Blair was in full Queen B mode. She was determined to impress the Yale rep, and she wasn't about to let Serena steal her moment.
The tension was thick.
Blair smiled sweetly at the Yale recruiter. "You know, I've always admired Yale's legacy of strong female leaders."
Serena, standing nearby, laughed lightly. "Blair, weren't you considering Princeton last year?"
Blair's smile tightened. "Oh, I've always been Yale at heart."
It was a subtle dig, but I could see the way Blair's posture stiffened. Serena wasn't just letting Blair win.
Chuck leaned over to me, amused. "I give it five minutes before someone snaps."
I smirked. "Two."
And I was right.
Blair, desperate to make Serena look bad, told the Yale rep about Serena's wild past—drinking, partying, and disappearing. But before Serena could fire back, a scandal hit.
A Gossip Girl blast went out, exposing that the person escorting the Ivy reps was none other than a former escort himself—Carter Baizen.
The room erupted.
I watched Serena and Blair's reactions. Blair was smug, Serena was shocked, and Chuck… well, Chuck was just entertained.
"Looks like someone's future just got torched," he murmured.
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The Fallout
By the next day, the damage was done. Blair had made her move against Serena, but it hadn't gone unnoticed. Dan had lost his essay spot to someone with more connections. And Nate was still stuck in the shadow of his father's expectations.
I caught up with Nate after school. He looked frustrated.
"You okay?" I asked.
He sighed. "My dad wants me to get into Dartmouth. But I don't even know if I want that."
I nodded. "Then don't do it for him. Do it for yourself."
Nate laughed bitterly. "Easier said than done."
I clapped a hand on his shoulder. "You're Nate Archibald. You'll figure it out."
Because if there was one thing I knew, it was that people like Nate didn't stay lost forever.
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Final Gossip Girl Blast
"Well, well, Ivy Week is over, and not everyone made the cut. B tried to sabotage S, but it looks like she got burned too. And poor Lonely Boy—turns out, connections matter more than talent. Tough break, kid. But don't worry, there's always next time. Or is there? You know you love me. XOXO, Gossip Girl."
I closed my phone, watching the city lights flicker in the distance.
This world was brutal. But that's what made it fun.