Charles Herman-Wurmfeld's 'Kissing Jessica Stein' (2001)

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.

-Rainer Maria Rilke, Letters to a Young Poet

Kissing Jessica Stein is something of a rarity in a couple of respects. First, it is an intelligent romantic comedy. All of the ingredients of a classic, mainstream rom-com are here — two people meet cute, begin a relationship, encounter an obstacle, and overcome it — but Kissing Jessica Stein asks its audience to think a little about sexual identity and things don't wrap up neatly at the end. Second, the film explores the relationship of two women who are choosing to be queer in a way not meant to titillate men, both in the film and in the audience.

An editor for a New York newspaper, Jessica has become frustrated with dating and spends her sleepless nights painting pieces that she does not display and reading mountains of books that fill her apartment. After her bitter and generally surly ex-boyfriend-cum-boss Josh lambastes her for being too critical of the men she has dated, Jessica decides to try something completely different and answers a personal ad from the women-seeking-women section. She meets Helen, a curator of a contemporary art museum who juggles three boyfriends but wants to explore sex with other women. The two women click and despite their conflicting attitudes about sex — Helen wants to get to it while Jessica doesn't feel that comfortable — they begin a relationship. Trouble arises, as it always does, when Jessica doesn't tell Helen about her brother's upcoming wedding and Helen gives her an ultimatum: take Helen to the wedding or break up. Jessica tells Helen that she cannot come out to her family, but her worries are assuaged after her mother reveals that she knows about their relationship and she supports Jessica. However, Helen soon realizes that Jessica really wants the best friend quality of her relationship with Helen that she could not find with men and that Jessica has confused a few moments of sexual desire with a sexual attraction to Helen.

This post is the first that has made me balk at the director as auteur theory that has dictated the titling of these posts because Kissing Jessica Stein is very much the product of co-stars, co-writers, and co-producers Jennifer Westfeldt and Heather Jurgensen. This project started in an improv theater class where they met and turned some sketches into a stage play. The play became a screenplay, which was purchased by a production studio and then bought back by Jurgensen and Westfeldt to finally be made into an independent film. These women have put a lot of effort, love, and themselves into creating Jessica and Helen's relationship, which translates onto the screen. Their chemistry truly sparkles as they create Jessica and Helen as fully realized, realistically flawed individuals. They are supported by an excellent cast of mostly theater actors, with Tovah Feldshuh and Jackie Hoffman particularly standing out as Jessica's very Jewish mother and pregnant co-worker respectively. Also, watch out for Idina Menzel as an enthusiastically curious bridesmaid.

I've been reading a particular website that focuses on queer women in entertainment for over a year now, and while many older lesbian-themed films have garnered quite a few references during that time, Kissing Jessica Stein has only been mentioned twice, both times in negative contexts. So I have to imagine that a section of the queer community does not like this film based on content rather than quality, and I can see why. As I mentioned previously, this film portrays two women choosing to be queer, and since many queer individuals think that homosexuality is biologically determined they may balk at the idea of being queer by choice. Indeed, an abbreviated form of this argument appears in film within the discussion between Martin, Sebastian, and Helen at a flea market. Lesbians in particular are wary of the concept of queer by choice because the idea is often conflated with the I Kissed a Girls who engage in lesbian sexuality to arouse their boyfriends. Personally, I see a clear difference between the two, the former being an understanding of one's queer identity and the latter being a consequence of heterosexual men's appropriation of lesbian sexuality for their sexual pleasure as a way to control women's sexuality. In fact, a real highlight of this film for me is the seduction scene in the restaurant because it acts as a reclamation of lesbian sexuality from straight men. When two men approach Helen and Jessica in a restaurant not realizing that they are on a date, Helen baits them into talking about why men find lesbians titillating. While the men describe what turns them on about two women together, Helen fondles Jessica under the table, thereby using the men's expression of how lesbian sexuality excites them to arouse her girlfriend.

The ending also causes problems for some queer women because Helen and Jessica don't stay together. Again, I find it refreshing to watch a romantic comedy that explores a relationship that isn't "the one," the one that supposedly lasts forever after the credits roll, and I don't think that the film criticizes Helen or Jessica for being in a queer relationship because they do not end up together. Many people dislike that Jessica runs into her ex-boyfriend Josh at the end of the film, because they interpret the encounter as evidence of the bulk of bi-phobic rhetoric, namely that bisexual women will ultimately leave relationships with women and retreat to the safe world of heterosexuality. First, I see the scene as more of a conclusion to Josh's storyline. He plays a prominent role in much of the film, so for him to disappear after the wedding, his passion for writing newly reawakened, would feel like his character arc had been left unresolved. Second, even if Jessica does get back together with Josh sometime after the credits roll, so what? Jurgensen and Westfeldt didn't write a film about Jessica and Josh's relationship: the movie is about Jessica and Helen and how their well-developed and respectfully presented relationship affects each other in believable, positive ways. In Helen's case, she seems to realize that she prefers relationships with women and begins dating another woman, while Jessica has become generally happier and less neurotic, quitting her job to pursue her art, and the two remain good friends. It's difficult for me to be unhappy with that ending.

Calling Kissing Jessica Stein a movie about lesbianism or even bisexuality is perhaps both inaccurate and limiting. This film explores the fluidity of sexuality and the tenuous line between friendship and romance with warmth, intelligence, and humor. The missteps, if one can call them that, are few. Helen's easy transition from dating three men to one slightly frigid woman seems suspect and Josh's transformation from embittered to sensitive could have used another scene. But mostly I have only extremely positive things to say about this rather groundbreaking and insightful film, which has become a favorite.