Jessica Stein (Jennifer Westfeldt) is a 28-year-old copy editor at a New York City newspaper. Helen (Heather Juergensen) runs a downtown art gallery. Simultaneously fed up with the pathetic hetero dating scene, they meet through a personals ad, in which Helen has quoted the “very profound” Rilke. Though Jessica frets for a minute that the ad appears in the Voice‘s “Women Seeking Women” section, she takes a breath, reflects on her terrible luck with me, and decides to check out the Rilke chick.
The premise of Kissing Jessica Stein is a familiar one in filmic romances: opposites attract. And so, even though both Helen and Jessica admire Rilke, they must also be established as very different from one another, thus producing a neat little detonation of comedic heat and hijinks when they meet. And so: you see Jessica at work (which is, to be fair, a nitpicky job by definition), where she is often judgmental, sometimes anxious, and completely sweet, a Jewish girl from Scarsdale who wolfs down Hagen-Daas and then goes jogging in the morning.
Kissing Jessica Stein
Jennifer Westfeldt, Heather Juergensen, Tovah Feldshuh, Scott Cohen, Jackie Hoffman
US theatrical: 13 Mar 2007 (Limited release)
Feeling pressure from her mom (Tovah Feldshuh) to “settle down,” Jessica is not a little nervous that maybe her own standards are, well, too high. But then, so as to assure you that said standards are really not out of line, the film provides a quick glimpse of the men she has to pick from—primarily, her current boss and former boyfriend (from college), Josh (Scott Cohen), also judgmental and anxious, but not very sweet, as well as a series of “bad dates” (male). These appear in a jaunty montage, all seated at the same table in the same little restaurant, all doing something egregious (think: the “dogs” sequence from She’s Gotta Have It).
If Jessica combines Annie Hall and Alvy Singer, Helen is more a mix of Madonna’s Susan (as in, once Desperately Sought) and gee, Nola Darling (you know, from She’s Gotta Have It). Helen is also introduced as not being entirely pleased with her life situation. Though the gallery biz is hopping, she feels energized by her yoga sessions, and she wears very cool outfits, Helen’s life is cluttered but not so fulfilling. She’s is seeing three different guys, from whom she gets different pleasures (for example, one is a delivery man for the gallery, with whom she enjoys “illicit” back room sex during show openings).
Even the breakdown of these issues comes in efficient doses—Jessica talks about her stuff with her best friend at work, the happily pregnant Joan (Jackie Hoffman), and Helen chats with her two best friends, the gay couple Martin (Michael Mastro) and Sebastian (Carson Elrod); they helpfully (and rather schematically) offer differing views on her suggestion that she “try” lesbianism. One gives her the you-go-girl okay, while the other thinks she’s dabbling in an area—sexual orientation—that needs to be treated with more seriousness.
Directed by theater veteran Charles Herman-Wurmfeld, from a script that Westfeldt and Juergensen adapted from their own off-off-Broadway play, Lipschtick, the film exhibits an affection for New York, offbeat sensibility, and comic rhythms that seem derived from Woody Allen. Still, and quite unlike Allen’s pictures, Jessica Stein actually appears to like its women characters. Even more daringly, it suggests that love and sexual attraction are not functions of gender or even a fixed-for-life self-identification, per se. Kissing Jessica Stein remains loosey-goosey concerning categories, and whether you see this as evasive or pleasant may be predicated on what you come in with. It’s not a lesbian film, it’s not a straight romance; indeed, its overt lack of investment in traditional identity politics is more innovative and refreshing than its more regular, rather sit-commish inclinations. But while Kissing Jessica Stein‘s lapses into formula are distracting, they are not devastating. They only make you wish that everyone involved had pushed a little harder away from the inclination to the “broader” demographic.
These lapses do occasionally weigh down the otherwise amiable and even adventurous proceedings. Predictably, the couple’s ostensible differences in style and affect only barely cover over their essential compatibility, and their capacities to nurture one another. Both love art, Helen has actually made it her day job, while Jessica aspires to be a painter, working on an easel in her apartment. Soon, Helen is encouraging Jessica to pursue her passion as a potential career. As well, Helen believes that she doesn’t “need anyone,” and wouldn’t you know, as soon as she says she never gets sick, whooomp, cut to the next shot and she’s sneezing and sniffling in bed, sipping Jessica’s fabulous chicken soup (as a matter of fact, this is reminiscent of the scene in She’s Gotta Have It when Opal tries to seduce Nola…).
By the time the women make the decision to “do it,” they’ve had several dates, adorably started and stopped while trying to figure out just what it means to be “lesbian” or be “with” a woman. Whether wrestling on the sofa, calibrating the ideal ratio between “sexy” and “ugly” (just how attractive is Harvey Keitel, anyway?), sharing info on how to blend the perfect shade of lipstick, making up stories to confuse two guys who try to pick them up at a bar, or contemplating the use of appliances (dildos or what?) and labels, the women are indeed quite charming, if calculated.
The most intriguing idea here is that Jessica and Helen’s interactions have less to do with their sexual harmony, or even desire, than with their developing sense of intimacy. Unlike every other romantic comedy on the block, this one is less interested in sexual intercourse than emotional connections, even if (again, predictably) Jessica worries over any kinds of connections. This might actually mean that it’s not strictly a “romantic comedy,” in that the resolution is not a happy coupling (in fact, Jessica’s potential choice, left open at film’s end, might even look a little painful…). Still, such a focus on the varieties of intimacy goes to the film’s resistance to conventions, quite despite all the generic conventions it heaps up along the way. Maybe it’s really about exploring other options, remaining mobile rather than stable, taking chances, and not swallowing whole that your objects of affection must be dictated by cultural norms or expectations that you’ve had drilled into your head since you were six years old. Maybe. But it’s hard to be sure.