Astor's (Fran Kranz) happy tenacity spoils his one chance at love with his lifelong crush Mila (Beau Garrett). Convinced he needs more experience with women to win her back, he engages her ex-best friend Cali (Dichen Lachman) to teach him how to woo women. Together they dissect his failings, and Astor makes his awkward pick-up attempts. As Astor begins to juggle multiple opportunities, he discovers the source of the rift between Cali and Mila, and the trio are forced to confront their conceptions about love.