Impossible - Eddie Munson

Mary was always weird. Being the baby sitter for freak Byers's little brother and his friends had perks though. She had the best excuse to play D&D.

And when Eddie Munson finds out she's the Dungeon Master for a group of middle school boys, it makes him think he was right to call her pretty. Because pretty and weird is his favorite combination.

Pre-Season 1 through Season 4
Slow-ish buildup. Story picks up speed in season 3.