Cher Horowitz and her friend Dionne, two of the most popular sophomores in school, play matchmakers for two teachers. Inspired by their success, Cher takes under her wing Tai, a "clueless" transfer student. While trying to make an advantageous match for Tai, Cher attempts to find a boyfriend of her own. Several misfires take place, due to poor communication, before she finds the Baldwin of her dreams.