The plot revolves around a date-for-hire (Cook) who is so horrible, he has women running back to their ex-boyfriends. When his best friend comes looking for his help, Cook falls in love with the guy's ex-girlfriend. Chaos ensues. Biggs will be playing Cook's best friend. Caplan will be playing the roommate of Kate Hudson, who is also appearing in the film.
Pretty in Pink's Howard Deutch is directing. The film is currently shooting in and around the Massachusetts area.