15 Of The Hardest "Would You Rather" Questions For People Who Love "Gossip Girl"

Are you a Blair or a Serena? 💋📱 Take this Gossip Girl Would You Rather quiz and face 15 of the hardest Upper East Side choices — XOXO, Gossip Girl! 🗽👑✨

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Spotted: You, trying to survive the cutthroat world of the Upper East Side. 💄✨ Whether you’re team Blair or Serena, crushing on Nate or Chuck, or secretly rooting for schemers like Georgina, you know Gossip Girl is all about high-stakes choices, backstabbing, and beautiful chaos.

➡️ Would You Be Gossip Girl or Her Victim? Take the Quiz to Find Out!

But what happens when you’re the one making the impossible calls? Would you risk your reputation for love? Protect a secret that could destroy your best friend? These 15 “Would You Rather” questions drop you right into the middle of Manhattan’s most scandalous storylines, forcing you to pick a side — no matter the cost.

➡️ Pick A City To Live In, And I’ll Reveal Which 'Gossip Girl' Character You Are

Grab your headband, your designer bag, and your best smirk — because in this world, you’re either in or you’re out. 💋📱✨ XOXO.

Would you rather…?

Be Queen Bee at Constance but have no real friends 👑👭Be invisible at school but have one loyal best friend 💛👯

Would you rather…?

Date Chuck Bass and deal with his dark side 🖤🍷Date Nate Archibald and risk his wandering heart 💘⛵

Would you rather…?

Keep Blair’s biggest secret even if it hurts you 💔🎀Expose Serena’s latest scandal for your own gain 😈🍾

Would you rather…?

Be the target of Gossip Girl’s next blast 📱💥Be the anonymous tipster leaking juicy gossip 💻👀

Would you rather…?

Lose your family fortune but keep your social standing 💸👑Stay rich but become a social outcast 💰🚫