Astor's happy tenacity spoils his one chance at love with his lifelong crush Mila. Convinced he needs more experience with women to win her back, he engages her ex-best friend Cali 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.