My First Mister

After graduating from high school, Jennifer (Leelee Sobieski) finds a job in an upscale boutique, charms her new boss, Randall, with her quirkiness and exhibits a surprising talent for the business. The beginning of their friendship is filled with energy and excitement, but it soon becomes complex as Jennifer develops an infatuation for Randall, who is twice her age. Though Randall is flattered by the attention, the age difference and his failure to keep a profound and tragic secret from Jennifer sends her on a quest across the Southwest that has far-reaching consequences. Through the journey, her damaged life begins to heal, and she learns about true love and real friendship.