Favourite Films: Kissing Jessica Stein

Kissing Jessica Stein is a movie that kept coming back to me in so many different ways and in so many different periods of my life—so it’s where I will devote my energies today.

When the film was first made, it was the early 2000s. I remembered the trailer so vividly because I had never heard of a movie before about two women in love. For a while, I became obsessed with this film, but since it was the early 2000s and I was still too young to rent anything, it faded from my memory. The film also had to be re-branded, I would later learn, since the NYC skyline with the Twin Towers in the background had to be removed in the wake of 9/11.

The movie didn’t do that well, either. The film’s plot is relatively simple, and even a little weak on the surface, especially with how it treats bi narratives. Jessica Stein is running out of men to date in her single life in New York City, and then decides she may as well try to date women. Though the actual spark of attraction between Jessica and Helen is a little bit better than the whole “I’m out of men, may as well try women” trope–I can definitely see why not a lot of people like this film. It can seem a bit iffy on the surface in terms of representation. Rather than getting into a debate about the politics here, I want to instead focus on what I saw as the real spark of attraction between Helen and Jessica: the poet Rilke. Jessica laments her crappy love life by reading Rilke, and so when she sees a personal ad that quotes him, she believes she has found the love of her life. It just so turns out to be in the women loving women section of the paper. She is shocked at first–but can’t get the poet or the writer of the ad out of her head. And so, she goes for it.

“Going for it” is what I see as the point of this movie. Jessica is in a rut. She works at a newspaper but they tear apart her writing. She is uptight and doesn’t know how to relax. She likes to paint, but doesn’t really do it anymore. Her mother wants to set her up with a good Jewish man, but all the dates she goes on bomb. She is in a rut, so clearly, and so it’s not just that Helen is a woman that interests Jessica. She’s into Rilke; she’s relaxed; she likes yoga and different types of food. They click because they are so different, and the sexuality angle is one of many.

When I was finally able to watch this movie in its entirety, I was old enough to understand the bad ideas about bisexuality it could possibly represent. I was dating women and men–but I was still so much like Jessica in so many ways. I wanted to break free of all the shit that bound me, and so, it didn’t matter that this movie had some problems. I could only see it as a solution. I won’t say too much about what happens between Helen and Jessica, but the ending of the film stuck with me for years. Their relationship seemed like so many of my own. It was strange. Weak. Rough and messy, but also deeply caring. There is a montage scene of how their relationship progresses at one point, and my favourite part was when Jessica took care of a sick Helen because it was so banal, yet so sweet. I had never seen intimacy between women like that before. It moved me for years afterwards.

I would watch this movie again, almost a decade later, after I married my husband. I was surprised to find that it still moved me in ways I couldn’t quite recall. Rilke was a poet who I actively taught in my classes, and I had now worked in a similar office as Jessica. Everything about the women’s lives were familiar to me, so what truly stood out this next time watching the film was the relationship between Jessica and her mother. Helen is not Jewish–yet she goes to a Seder with everyone, and since they are two women, they are not assumed to be together. They stay in Jessica’s childhood room, where they make love for the first time. It is only much later that the mother realizes what had gone on between them. Instead of reverting to the standard homophobic parent–which could seem so easily with a family deeply religious and meddling as this one–instead the mother accepts Jessica, and Helen, no matter what.

This is such a small, silly movie. But I still think it’s amazing that over the past twenty years, I’ve come to it at three very different stages of my life, and still found something good in it. I can only hope you will too!

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