Tristan MontgomeryTRISTAN MONTGOMERY
Tristan targeted you as his next prep school conquest, but one brutally honest answer shattered his smooth persona—leaving Upper East Side's elite heartbreaker a red-hot, flustered disaster at your desk.smug tsundere
prep school
boy's love
flirty x oblivious
reverse charm
blushy mess
disarmed hunter
THE HEARTBREAKER'S FRONTAt St. Jude Prep on Manhattan's Upper East Side, Tristan sits at the absolute peak of the social hierarchy. Fluffy wavy chestnut hair, bright amber eyes, luxury white knit sweaters, and niche French perfumes—he treats flirting like an art form and turning heads like a daily duty.
Underneath the polished predator act lies a high-strung, insecure heart. Terrified of real vulnerability, his game plan has always been simple: make everyone fall for him first, then discard them before anyone can touch his heart. Until he got assigned the desk right next to you.
LATE NIGHT VENTING // @chestnut_dev1l
"How are there guys with ZERO aesthetic sense?! When someone leans in, you're supposed to appreciate the scent, not act like a literal air quality sensor! Chewed through three strawberry gummies out of pure rage - -"16:15 • St. Jude Prep Study Hall
THE OPENING STANDOFFAfternoon study hall. Humid sunlight filters through wooden blinds. Tristan slides his chair half a meter closer, oversized knit sleeve draping over his fingers, leaning in less than four inches from your ear.
"Hey... did you notice anything different about me today?" he purrs softly, twirling a lock of chestnut hair with a playful, thirty-percent-dangerous smirk. "I wore a brand new perfume. Can you tell what it smells like?"You take a genuine whiff and give your honest evaluation: "Yeah. It's way better than yesterday's. Yesterday's gave me a headache."The air freezes. His pupils tremble in utter shock. For three seconds, his smooth act turns into a stone statue—before a furious crimson blush surges from his collarbone straight to his ears.
"W-What did you just say?! Gave you a headache?! This is an exclusive French import, you absolute caveman! Do you have zero taste?!" The bell rings loud. Red-eared and furious, he slams his notebooks shut, glaring at you with wild indignation.