Friday, April 23, 2010

Jennifer Westfeldt & Heather Juergensen: The Duo Behind "Kissing Jessica Stein"

It’s no secret that many heterosexual men are very intrigued by the thought of two women hooking up. There’s one scene in “Kissing Jessica Stein” where the two main characters (Helen and Jessica) try to get to the root of this pressing issue. They casually start up a conversation with a couple of guys at a bar, and while the men tell them what they think is oh-so-hot about two women together, Helen completely takes a metaphoric hold of the moronic drivel spewing out of these guys’ mouths and uses this opportunity to loosen Jessica up, by touching her leg under the table. Here the women are taking a popular male fantasy, which undoubtedly not only objectifies women but contorts homosexuality for a specific male purpose, and they actually get off on it. Meanwhile, the guys have no idea what’s going on under the table. This scene is not only hilarious, but it is unexpectedly feminist. And it’s just one reason why I love “Kissing Jessica Stein.”

Both Heather Juergensen and Jennifer Westfeldt were true auteurs from the film’s inception. They both lived and breathed this movie; not only did they write and produce it, but they starred in it as well. After meeting in an acting workshop in 1997, Heather Juergensen and Jennifer Westfeldt penned an Off Off Broadway play which they both starred in. It was called 'Lipschtick,” and it was basically “Kissing Jessica Stein” 1.0. After the play garnered a bit of buzz, they were inspired to turn it into a movie. So they wrote a screenplay and by 2002, “Kissing Jessica Stein” was in theaters.

Jennifer Westfeldt described their creative process: “We were just sort of learning the language of film because the dialogue came so easy to us as actors. We had a million scenes we wanted to write but that wasn’t ever the problem. It was just how do you make it visual, how do you make the characters more different, how do you put it into shorter scenelets rather than the long way we might have at the outset.” (

Westfeldt plays Jessica Stein, a neurotic New York journalist who feels pressured by her Jewish mother to settle down and find Mr. Right, preferably right now. Jessica is fed up with bad dates and is at somewhat of a crossroads. She then comes upon a personal ad with a quote from one of her favorite writers. Even though Jessica defines herself as very “straight,” she decides to answer the ad, which is in the Women for Women section and was placed by Helen, a bisexual (played by Heather Juergensen). This gives way to an interesting and very funny exploration of sexuality and friendship. Jessica gets caught up in technicalities. At one point she even brings out a lesbian sex handbook. Even when she tries to loosen up, Jessica is extremely rigid (both mentally and physically), and Heather just wants to “go with the flow.” After a while, things seem to be going great. Both women completely connect and seem in synch, but Jessica stops wanting sex and that becomes a problem for Helen. Sarah Warn, of does a good analysis of their relationship, and points out that “Ultimately, both women come to realize that Jessica is attracted more to the idea of Helen than to Helen herself, and that they both deserve better than that.” (

I’ve read quite a few reviews on the movie, and what they fail to point out is that Jessica feels so comfortable with Helen because she has finally found her best friend. They connect on every level outside of a sexual one. In the end they realize they weren’t right for one another, but they still stay friends. I think the film portrays lesbianism and bisexuality in a positive light and asserts that queer relationships between women are often based on intimate friendships.

Jennifer Westfeldt and Heather Jurergensen completely immersed themselves in these characters. Their script was filled with little nuggets from their lives or stories they had heard from friends. Westfeldt talked about working with her writing partner: “There were things about Heather that are so Helen-like that I would notice. She would just say with absolutely no awareness that they might be funny or off color. One of the Heather-isms that made it into the film—she was like “I like ugly; I’d do ugly.” It was such a moment of understanding. When you’re in a new friendship as well as a new collaboration, you notice what’s good fodder for material when you see the differences that someone brings to the party. We had a very different outlook on things. We had both had scores of bad dates and scores of issues with men, but we had a very different take on it [and] a very different way of talking about it. So it was nice as writers to look at eachother and realize ‘Oh that we gotta remember. That’s a good one. We have to exploit that and go further with it.’ Because so much of good writing is to take a truth and then explode it and take it to its furthest extreme to see what you can find.” (

This film only got made because its two creators worked at it tirelessly. With a budget of $1 million, it ended up grossing over $7 million at the box office (,
Heather Juergensen remembers their struggle: “From the point of getting it back in turn around to having the film in the can was like nine months because we just went fast and furious. We were just diligent that year in asking people and attracting investors and we greenlit ourselves by the skin of our teeth, but we managed to start rolling film. Then once we had something in the can and we were able to show people cut scenes or little trailers then we got the rest of the money to finish because we didn’t have enough at that point to even finish post production. The studio probably wanted more of a mainstream Hollywood film maybe like an ‘In and Out’ or something like that. The director we were working with wanted it to be a pure art house movie with none of the like broadly comic things we still have in the movie. We thought: can’t you have both, can’t you have some mainstream comedy and attract a wide audience but also have it be quirkier and more off beat than most Hollywood comedies? Obviously we weren’t stars. That’s already pretty quirky for a romantic comedy. They said that would never work, you’ll lose both audiences and gain neither. And we thought hey, why can’t you get them both, why can’t good just be good if you make a good movie people will come even if you’re nobodies. We kept sort of kept saying ‘look at The Blair Witch Project,’ ‘look at The Full Monty.’ We would use these examples of movies with no stars in it that made money because they were interesting to the public for one reason or another. So when we were our own bosses we could say ‘that will work’ or ‘that won’t work.’ (

“Kissing Jessica Stein” made me wonder about a lot of issues, including the role sex plays in queer relationships. What if Jessica and Helen had stayed together? Would she have counted as a “real lesbian” if they had stayed together but were celibate? Would being celibate really make her any less of a lesbian? Maybe she is just at a different place on the lesbian continuum than more sexual lesbians. A heterosexual is no less of a heterosexual if he/she is celibate. But the “no sex” thing is a problem for Helen because she is a very sexual person. I think a lot of people think of lesbians as some kind of sexual perverts, and this is due to heterosexist notions of “normal sex.” Is Helen a fair representation of a bisexual? These aren’t questions that can be easily answered. I just think it is great that two women created a film which raises questions. Life, relationships and sexuality can get complicated, but it’s important for people to be aware of these issues and to discuss them. “Kissing Jessica Stein” certainly stirs up conversations (and laughs) every time I watch it.

Works Cited:

Box Office Mojo. “Kissing Jessica Stein.” 2002.

D'Emidio, Tiffany N. Life in the District. “Kissing Jessica Stein (with Jennifer Westfeldt and Heather Juergensen).”

Video Detective. “Kissing Jessica Stein: Jennifer Westfeldt-On Writing The Script.” 2002.

Warn, Sarah. “Review of ‘Kissing Jessica Stein.’” 2002.

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