Rae has earned the infamous title of Groom Maker. With twelve ex-boyfriends having gone on to marry the next woman they meet, everyone believes her record is no coincidence. When Trent, the owner of her rental house, tells her to move out, she's devastated. Without that house, Rae's dream of owning her own salon will crumble. The two agree on a bet. Rae will date Trent, and if she can convince him to leave the bachelor life and settle down, she will win the right to stay in the house. Otherwise, he'll kick her out. Will unexpected feelings make a bigger mess or create a new dream for both of them?