The film is the story of an alienated teen (Leelee Sobieski) who forms an unlikely friendship with a lonely clothing store manager (Albert Brooks).

In an effort to secure employment at the upscale Century City Mall in Los Angeles, Jennifer, a 17-year-old "goth" girl who just graduated from high school, makes a nuisance of herself at a clothing store run by 49-year-old Randall Harris, who eventually hires her on a trial basis as a stockroom clerk.

Encouraged by her initiative but concerned that her appearance may frighten away potential customers, Randall buys her an appropriate outfit and promotes her to saleswoman.

Made aware that J is unhappy living with her mother (who seems to pay more attention to her two pugs than her daughter) and stepfather, Randall offers her an advance on her salary so she can afford her own place, then helps her find an apartment.

Their friendship restored, Randall reluctantly accompanies J to a cemetery to lie on the graves of the deceased to feel their "energy", something she does regularly.

In the film's DVD commentary, director Christine Lahti noted Albert Brooks campaigned vigorously for the role of Randall, and that although initially doubtful about whether he could handle the heavy dramatic aspects of the character, she was won over at their first meeting.

Lahti expressed deep disappointment that the film was rated R (for language), despairing that it would likely not be seen by many teenagers who would like and relate to the characters.

"[5] Lawrence Van Gelder of The New York Times wrote, "Of all the odd couples who inhabit film, surely among the most endearing are Jennifer and Randall, the lost souls and repressed good hearts at the sweet, sentimental center of Christine Lahti's life-affirming My First Mister.