"You're a player, you flirt with every girl you can get your hands on, and I bet you can't date a girl for two days, let alone thirty!"
All throughout high school, Jack Gilinsky and Marley Santana lived in polar opposite worlds, and because they each pursued different lifestyles after graduation, it didn't seem likely that they ever would cross paths. But when the two are suddenly brought together through mutual friendships, they're forced to spend more time with each other than ever imaginable. She finds herself having to constantly knock down his enormous ego, while he's completely fascinated by her apathy towards his undeniable charm. When enough becomes enough for Marley, they make a bet that neither of them could resist: she has the opportunity to get rid of him once and for all, and he scores a chance to win over the girl of his dreams.