Kissing Jessica Stein

Spoiler alert: Kissing Jessica Stein ends with the main character in a heterosexual relationship. However, Kissing Jessica Stein is so charming, witty and dynamic that I’m not even mad about it.

Kissing Jessica Stein is about early-2000s neurotic working woman archetype, Jessica played brilliantly by Jennifer Westfeldt. After coming to a stall in her dating life, Jessica responds to an anonymous ad in a personal column. The ad turns out to be from Helen, an artsy bisexual. From here, the movie shows the stops and starts of their relationship as the previously (and perhaps currently) heterosexual Jessica embarks on a relationship with Helen. More trouble comes when Jessica is not willing to acknowledge their relationship to her family.

What’s quite remarkable about this movie is that it touches on sexualities other than homo and heterosexual with some depth. It also doesn’t spoon-feed its audience what these characters’ sexualities are. You can read Jessica as sexually experimenting with Helen or as a low-level bisexual. If you wanna get even more complex, you could read her as a biromantic heterosexual. That seems to fit with her very romantic relationship with Helen but lack of sexual interest. Kissing Jessica Stein is one of few well-done looks at bisexuality, sexual experimentation and the difference between romantic and sexual attraction. And their tackling of this subject matter feels effortless and fits into the wider narrative. It really is impressive to see, especially in a movie from nearly 20 years ago.

The writing in Kissing Jessica Stein is great. There’s a lot of examples I could give but let’s talk about the big one. I actually liked the male love interest. Despite my overwhelming bias towards queer relationships, early on in this movie I knew that the endgame couple would be Jessica and her coworker Josh. And I was fine with this. They genuinely seem well-suited for each other and Josh seems like a nice guy. Kissing Jessica Stein also gets them together without villainizing Helen. Helen and Jessica end the movie as friends. This is another delightful bonus in this story that keeps giving me what I want.

Kissing Jessica Stein is one of the best portrayals of sexual experimentation and the complexities of sexuality I’ve seen onscreen. If you can get past the heterosexual endgame (which the quality writing of the film certainly helps you do), this is a really charming comedy. Kissing Jessica Stein has a good cast, great energy and some surprisingly progressive views on relationships and sexuality for a rom-com made in  2001. Absolutely one to check out.

Overall rating: 7.9/10

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