The Upper East Side didn’t often slow down, but somehow, you convinced Blair Waldorf and Serena van der Woodsen to spend one quiet night in your apartment—no parties, no galas, no gossip.

Just a sleepover.

It started innocently enough: silk pajamas, piles of pillows, chocolate truffles, and the sound of rain tapping against your window. Serena was sprawled across the couch, hair a golden mess, sipping wine straight from the glass. Blair sat cross-legged on the rug, scrolling through her phone, pretending not to enjoy herself.

“This feels… weird,” Blair said finally. “Shouldn’t we be at some exclusive event right now? Wearing couture?”

Serena laughed. “Blair, not everything has to be on Page Six.”

You smirked, setting down your drink. “Relax, Waldorf. Consider it a detox from your own drama.”

Blair arched a brow. “My own drama? Please, as if you and Serena don’t have enough to fill a miniseries.”

Serena grinned, tossing a pillow at her. “You’re just scared we’ll talk about you tonight.”

And just like that, it began.

It started as a game of Truth or Dare, but Blair quickly changed the rules. “Truth only,” she said, pouring more champagne. “No dares. Just honesty. I’m in the mood for emotional destruction.”

Serena groaned, laughing. “Blair, this is supposed to be fun.”

Blair smirked. “Oh, it will be.”

The first few rounds were harmless—favorite designer, worst date, most embarrassing moment. But the longer the night went on, the deeper the questions became.

“Who was your first real love?” Serena asked you, leaning close, eyes glinting.

You hesitated. “I… think it was someone who didn’t love me back.”

Blair hummed. “Tragic. Classic. You’d fit right in with us.”

Then you turned the question on her. “What about you, Blair?”

Her expression softened for just a second before she smirked. “Love is a weakness. I prefer ambition.”

But Serena didn’t let it go. “That’s not true,” she said quietly. “You just loved the wrong people.”

The room fell silent. The rain outside got louder.

By midnight, the air was heavy with laughter and vulnerability. Serena admitted she still missed people she swore she didn’t care about. Blair confessed that sometimes, she wished she could stop trying to control everything.

You told them you never thought you’d be friends with either of them—that you always thought girls like them were untouchable.

Serena smiled, brushing her hair behind her ear. “We’re all just pretending to have it together. Some of us are just better at pretending.”

Blair rolled her eyes, but she was smiling too. “Speak for yourself, van der Woodsen.”