Emma has lived in Santa Barbara her entire life with her parents and lovely friends. She's had a simple life with no complications and has always kept it that way. In her Junior Year of High School, she's a little bored of the same old life and is willing to gamble her comfort zone for some fun experiences. And what could be more fun than falling in love? Zachariah has finally come back home after two years at a boarding school in England and this sweet little troublemaker has come back ten times worse. With a cigarette dancing between his lips, he screams trouble louder than he ever had before. Coming back into town, he's hoping to reunite with his friends. Noah, Barrett, Sebastian, Ava, and Emma. After finding out that sweet little Emma is looking for some fun, Zachariah offers her a bet. If he wins, she has to live with him for a month, in which he guarantees to make her fall in love. If she wins, he'll leave her alone for good. Their history of being best friends can't repeat itself. Not this time. This time, there's more to the two than just friends. This time they're going to bet on it and gamble for love.