LGBTQI Week: Kissing Jessica Stein

Ten years ago, I saw Kissing Jessica Stein on a date with my first girlfriend. We liked the movie, but when we walked out of the theater, we laughed and said to each other, “Let’s not end up as dysfunctional as those two!” The irony did not escape us a few months later, when we broke up under eerily similar circumstances as Jessica and Helen, the film’s protagonists. But much like Jessica and Helen, our break-up was the start of our lifelong friendship. I’ve re-watched the film countless times throughout the last decade, and objectively, I don’t think Kissing Jessica Stein is a great movie. It’s filled with too many romantic comedy clichés, and for a film about queer women in a relationship, the film is awfully preoccupied with discussions about men. But in its best moments, it authentically depicts the awkwardness of new relationships, the confusion of unexpected sexual attraction, and the deep friendships that result from failed romances. Kissing Jessica Stein is flawed, but its sincerity and its willingness to address relationships between non-monosexual women keeps me coming back to it, over and over.

Though words like “bisexual” and “queer” are never used, Kissing Jessica Stein is about sexual fluidity. The Rilke quotation mentioned throughout the film makes this theme obvious: 

“It is not inertia alone that is responsible for human relationships repeating themselves from case to case, indescribably monotonous and unrenewed: it is shyness before any sort of new, unforeseeable experience with which one does not think oneself able to cope. But only someone who is ready for everything, who excludes nothing, not even the most enigmatical will live the relation to another as something alive.” (Emphasis added)

Much like Alyssa in Chasing Amy, Helen places a personal ad in the Women-Seeking-Women section because she “excludes nothing” sexually. When it occurs to her that, in all her sexually adventurous years, she has yet to sleep with a woman, she decides to give it a try – hence the personal ad. But she’s completely unprepared for Jessica Stein – who Helen later calls a “Jewish Sandra Dee” – to respond. As the film chronicles the rise and fall of Jessica and Helen’s romantic relationship, it tackles some big questions: Can a woman who’s only dated men have a successful sexual relationship with a woman? When, if ever, is secrecy in a relationship acceptable? Can a relationship with high emotional connection and low sexual compatibility survive?

Jessica and Helen in Kissing Jessica Stein

Kissing Jessica Stein provides no easy answers to the questions it asks, which I appreciate. The film understands that sexuality is complicated, and not everyone shares the same capacity for fluidity and sexual experimentation. The film also understands that there is no definitive recipe to a successful relationship, because people are different and have radically different priorities when choosing significant others. Jessica and Helen start out coming from similar places – both of them have identified as straight for all of their lives, and both of them want to question that assumption and explore the possibility of dating another woman. In time, they find that they truly are attracted to each other – more than that, they love each other – but that attraction manifests differently in each of them. While Helen has no insecurities about a sexual relationship with Jessica and longs to have the kind of relationship with Jessica that she’s had with men in the past, Jessica is more interested in her emotional connection with Helen than her sexual one. I don’t think this means that Jessica is straight or that she isn’t genuinely attracted to Helen – we never see her in a relationship with a man, so it’s likely that her sex drive is naturally low. Rather than judging Jessica and Helen for their differences, the film shows both women as they are, and it explores the ways in which their differences both cultivate and destroy their relationship.

The biggest problem that I have with Kissing Jessica Stein is that it simply isn’t as queer as it wants to seem. As Stephen Metcalf wrote in his review at Slate, “It’s a shame that a movie about openness regarding sexual preference recycles so many motifs from the pantheon of great hetero-dating movies.” Though Kissing Jessica Stein addresses interesting questions and themes rarely found in your average romantic comedy, it’s also fairly formulaic. The stakes never feel quite as intense as they should; even when it becomes clear that the relationship is about to come to an end, there’s never any doubt that Jessica and Helen will remain the best of friends. And then there’s the issue of men. Neither Jessica nor Helen identifies as a lesbian, and I like that choice – the film does a great job of dismantling the gay/straight, either/or binary. That said, one would think that women who are attracted to other women might want to spend some time exploring that. There’s nothing wrong with Jessica and Helen discussing which male celebrities fall into the category of “sexy-ugly” (and I completely agree with their conclusion that Harvey Keitel is among them), but I found it hard to believe that they wouldn’t spend more time finding common ground on what they find appealing about women as well. It’s as if too much overt lesbianism would make the film hard for audiences to swallow. Too much of the film makes it feel like it was made for primarily straight viewers, and that feels like a missed opportunity.

Jessica and Helen in Kissing Jessica Stein

When I watch Kissing Jessica Stein now, I’m transported back to a very specific time and place. I remember being sixteen and newly out as bisexual. I remember anxiously anticipating my first kiss from another girl. I remember starting to understand that sexual expression can be flexible and doesn’t have to conform to societal norms. It shouldn’t matter whom we love or what we call ourselves – only that we love at all, and that we express that love in the most honest way we can. Kissing Jessica Stein is not the first film to convey this message, nor does it do it as well as some other films. It’s certainly not as risky as Shortbus, or even Humpday. But it captures a feeling to which many can relate. And even when it fails, it feels far more believable than most comedies of its genre.

Carrie Nelson is a Bitch Flicks monthly contributor. She was a Staff Writer for Gender Across Borders, an international feminist community and blog that she co-founded in 2009. She works as a grant writer for an LGBT nonprofit, and she is currently pursuing an MA in Media Studies at The New School.