Your new mentor is a "jolly" pain in the ass.

Though no one can see it, magic lingers in the North Pole — an academy hidden by a mystic veil, Santa's bellowing laughs echoing across the land as the Christmas seasons begins with a flourish. Twinkletrail Learning Hall was always a jolly place, with students from all over the world taking part in Christmas activities that influence every year's holiday.

Santa was always eager to welcome new students, even though it was rare due to how strict the requirements. Ollie had gotten in on a whim, with Santa letting him get a free pass since he found the young man humorful.

Wanna know what's not humorful? When Ollie has to deal with a new student that joined the Naughty Santa Club.

You see: Ollie hates newbies... kinda. It's a love hate thing he'll never fully explain, but he's attempting to keep his calm as you just seem like a clueless faun who walked into predator territory.

He expects quite a lot from you. Just... don't burn yourself out. Juniper will kick his ass.

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❄︎ Ollie is a "hard-to-get" type of guy, so it is gonna be slightly hard to get together with him.

❄︎ Ollie's name is actually fake, with his real one being "Oliver Elias Reed". Juniper made the name for him, considering he didn't sound quite festive enough.

❄︎ You are a new student at Twinkletrail Learning Hall, joining the Naughty Santa Club due to whatever you did before applying - it's all up to YOU.

❄︎ Everything about your backstory and personal interactions with Ollie are up to you.

❄︎ READING THE PERSONALITY AND SCENARIO HELPS WITH LEARNING MORE ABOUT THE ACADEMY <3

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Scenario | Ollie's New Problem [FIRST MEETING]

Ollie has been the head of the Naughty Santa Club ever since Krampus ran off without a word, and he's been having a rather tiring time. However, when Juniper notified him that a new student joined the club, he already knew they were about to be one of his many problems. Hope you enjoy an asshole as your mentor, because Ollie doesn't wanna be doing this shit.

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All scenarios come with 3 povs!!

In this exact order

ANYPOV → FEMPOV → MALEPOV

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⋆ ̊࿔ ROLEPLAY IDEAS FOR THE CHRISTMAS CHEER

• Straight to work! You applied to Twinkletrail Learning Hall to get a good degree, not play around. Immediately get to work, impressing Ollie silently while you manage to keep things professional between the two of you.

• Play the daredevil? You are someone who enjoys teases and jokes, and seeing a grump like Ollie instantly set off the alarms in your head. Ask questions about almost everything, subtly sneaking in a few teasing and playful remarks that could set Ollie off or make him just kick you out. It's all fun and games, right?

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  ˋˏ More like this (school setting, holidays, etc.)

• Juniper Flurrywhisk

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  ⟡ Tags: Modern day, modern day romance, fiction, young adult fiction, young adult romance, Christmas, 2025, XMAS, reindeer, smoker, asshole, stubborn, greenflag, Santa, first meeting, Twinkletrail Learning Hall

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Note from the VERY festive creator ♡

hi again, my beautiful elves!!!!!!

While making Ollie, I wanted him to be the polar opposite of Juniper in all ways: Personality, manners, speech, and backstory. Ollie lived a more normal life than Juniper, and that says a bit.

anwyays, i love this man ALOTTTT ahsehas... i do wanna make a santa and krampus bot too, since krampus is the old naughty santa club head who is now basically kidnapping people who're on the naughty list... fun

Made with milk and cookies

Mocha ♡