A first feature from acclaimed actress Christine Lahti (who won an Academy Award for her short film Lieberman in Love in 1995), My First Mister explores the delicate relationship between two unlikely individuals who bring each other out of their protective shells. Jennifer (Leelee Sobieski), the film's narrator, is a Goth-obsessed, tattooed 17-year old who absorbs herself in death-laden music and poetry. Just graduating from school and immersed in a dysfunctional relationship with her out-there mother (Carol Kane), she finds a job at a local clothing store as a clerk. Her boss, Randall Harris (Albert Brooks), is a rigid, middle-aged type, who becomes uncomfortable when Jennifer begins to spy on him and follow his moves. She then cleans up her act a bit and lands a position as a stockperson, and Randall begins to take an interest in her. After a few outings where they attempt to relate their lives to each other, they begin to become close friends, effectively building confidence and bridging their considerable age gap. Also included in the cast are Desmond Harrington, Mary Kay Place, and John Goodman as Jennifer's hippie father.