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Based on its premise alone, I had a lot of reservations about My First Mister (2001). You can’t swing a metaphorical dead cat without hitting a movie that depicts a May-September romance as the most normal and commonplace thing in the world. I knew that the young woman in My First Mister was only a teenager and I wasn’t sure I was ready to see that, even if the film did make some attempt to acknowledge how strange and potentially creepy such a relationship is. But I gave it a try anyway and I was delighted to be proven wrong.

My First Mister is the story of J (Leelee Sobieski), an angsty, death-obsessed teenager who gets a job at a Brooks Brothers-style menswear store at the mall and forms a weird bond with her boss, Randall (Albert Brooks), whom she promptly christens R. Their friendship is dysfunctional at first—he can’t resist pointing out how unappealing her piercings are, and on the first day they meet she asks him point-blank if he’s thinking of fucking her—but it grows increasingly affectionate. She’s miserable living with her well-intentioned mother and stepfather (Carol Kane and Michael McKean), so he helps her get her own apartment. She also drags him to the beach to get a tattoo in an effort to get him to loosen up. Then J finds out that R is in the last stages of leukemia and has only a few days to live. She drives to New Mexico to find R’s estranged wife but discovers his 20-year-old son (Desmond Harrington) instead and drags him back to California with her so he can meet R before he dies.

Leelee Sobieski is totally believable as an angsty teen. Her problems are fairly standard but she is nevertheless dealing with genuine emotional pain and doing a crappy job of comforting herself. Her parents are divorced and she doesn’t feel any connection to her chirpy mother, her stoner father (John Goodman), or anyone else at school. I love that Sobieski resists the temptation to do the traditional flouncy, eye-rolly teen performance but instead invests her character with real personality. She’s occasionally bratty and immature, but she’s not a cookie-cutter teen stereotype. Albert Brooks is also wonderful as a neurotic loner who’s afraid to get close to anyone. He invests every line with so much self-directed irony and humor, and he never comes across as predatory or leering. Carol Kane, John Goodman, Michael McKean, and Desmond Harrington are all fantastic as well, and there’s a hilarious and beautiful dinner party scene near the end of the film where everyone gets to meet and interact with each other. That scene alone justifies the use of the trope of the surprise terminal illness, which I normally find pretty dubious.

One of my favorite things about this film is that the writer (Jill Franklyn) and the director (actor Christine Lahti) don’t rush the relationship between J and R into a tidy category. Instead, they let it breathe and grow at its own pace. I kept finding myself thinking, “I get it, he’s like her father figure. No wait, they’re more like friends. No wait, it’s romantic love.” By the end of the film it seems to be a combination of all three, which I found incredibly charming and refreshing. J and R come to genuinely care about each other as human beings and allow themselves to be changed by each other in a way that feels earned, but the film also doesn’t shy away from the romantic elements of their relationship, such as they are.

I also love the film’s frankness about J’s sexuality. A series of voiceovers near the beginning, in which she describes her desires and romantic history so far, is both hilarious and surprising in its matter-of-fact-ness. But this attitude of openness continues throughout the film. It’s refreshing to see a film about a teenage girl treat her as a sexual agent, rather than as the object of various men’s desire. She’s inexperienced, and her virginity and desires are treated as completely ordinary, normal parts of her whole personality.

I’ve always thought it would be impossible to make Harold and Maude if you reversed the sexes of the older and younger character—there’s just too much cultural baggage around older men and younger women. This isn’t Harold and Maude, and it’s not trying to be. But My First Mister is a worthy addition to the unconventional love story canon.

– Ashley Wells watches too many movies and welcomes recommendations for more. Leave her one here or on Twitter: @ashleybwells. Spoiler alert: she has already seen Troll 2.

https://www.youtube.com/watch?v=4GcA7