Two people with seemingly nothing in common forge an unusual friendship in this comedy drama that marks the feature-length directorial debut of actress Christine Lahti. Jennifer (Leelee Sobieski) is a teenager in her last year of high school who feels cut off from the world around her. She uses black clothes, body modification, and a defiant attitude as a way of keeping the world at bay, but at heart she feels unattractive and unloved, while her parents -- cheerfully oblivious Mother (Carol Kane) and often-absent Benjamin (John Goodman) -- have no idea of how to communicate with her. One day Jennifer happens by a men's clothing store run by stuffy, middle-aged Randall (Albert Brooks); at first she makes fun of him, and he seems bemused by her, but she ends up asking for a job, and Randall gives her part-time work helping out in the stockroom. While Randall's strait-laced style is a 180-degree turn from Jennifer's goth-grunge persona, they soon learn they both have their share of problems with self-image and share a desperate need to be loved. Soon, "R" and "J" (as they like to call each other) have become fast friends, as she encourages him to take chances and try new experiences, and he tries to show her how to let down the walls she's built around herself and allow others to get to know the real Jennifer. My First Mister also features Mary Kay Place, Michael McKean, and Desmond Harrington.