We’re meant to place the title character of Kissing Jessica Stein (20th Century Fox) quickly. She’s a smart 28-year-old, sweet and likable, but neurotic and overly fussy; in her baby-blue sweater set, cat-eye glasses, and bunned-up hair, a bit of a prude and a Luddite (computers, she believes, “obscure our humanity”). By day she works as a copy editor in the warrens of something called the New York Tribune. Nights and weekends she paints (nothing too abstract, nothing too representational), scarfs Häagen-Dazs, jogs: all in all, a life of steady, riskless happy unhappiness. Then she finds out her older brother is getting married, on top of which her best friend is pregnant. Suddenly Jessica Stein is answering a personal ad placed by another woman, even though all evidence to date points to Jessica Stein being straight.
Over the next several months, and the course of the film, Jessica falls in love with Helen, who’s the author of the ad and, as it turns out, another erstwhile curious straight girl. Herein lies Kissing Jessica Stein’s peculiar strength: It’s not so much a study of sexual preference as of sexual attraction, in all its occult polarities and disappointments. But herein also lies the movie’s weakness: Having for the most part dispensed with seminar-table ruminations about sexual identity, Kissing Jessica Stein resorts to a series of When Sally Met Sally clichés. Sure enough, there’s the Manhattan skyline, blushing in the twilight, as the obligatory jazz-era soundtrack revs up in the background. Sure enough, there’s the comic sequence of Woefully Inadequate Dates, now as compulsory in feeling as the lutz or the double axel. (It was perfected already when Woody Allen introduced it in Annie Hall.) There’s the literary touchstone that brings the lovers together—Emerson in Next Stop Wonderland, Rilke here. And of course, the Harry Met Sally retread, of partners lying in bed with opposite expressions planted on their faces—one’s discovered bliss, the other sheer terror.
It’s a shame that a movie about openness regarding sexual preference recycles so many motifs from the pantheon of great hetero-dating movies: There was a lot of fresh sizzle to work with here. When we first meet her, Helen is eighth-edition Susan Seidelman, bound in leather—pants, in this instance. She’s a genial sexual prowler, an unburdened user. The filmmakers have set up a wonderful dissymmetry to play with: Jessica has responded to Helen’s ad because of a Rilke quote, which has touched her Ivy-trained soul. But Helen tossed in the Rilke glibly, at the suggestion of a co-worker who calibrates for her the poet’s manipulative power in the personals ad marketplace. Too bad this conceit is so quickly dropped—I’d like to have seen Jessica wax on about Rilke, and Helen forced to BS her way through. From their first date on, the movie favors girlish conspiracy over conflict, but not entirely to its detriment: One of the nicest scenes has Jessica and Helen lying together in Jessica’s childhood bed in Scarsdale, hemmed in by a wicker headboard and stuffed animals. For once the current running through them isn’t about whether they will finally have sex, and sure enough, well—badda bing, badda boom.
Kissing Jessica Stein started out as a series of theatrical sketches, written and acted by Jennifer Westfeldt and Heather Juergensen, the movie’s two leads. They have the give-and-take down pat: Juergensen’s Helen is all growling eyes and sexual license; Westfeldt is all earnest and shy affectation (when giggling nervously, which is often, she seems to be channeling Diane Keaton). In its journey to the screen, the routine has stayed a bit schticky and small; and when the film strays from the two women, it paints with some awfully broad strokes. Jessica’s grandmother is the inevitable potty-mouthed Golden Girl, while Helen’s male co-workers light up the gaydar like a Christmas tree. (For a movie that’s about living beyond stereotype, its straight men are unaccountably flat: Jessica’s boss is a bitter would-be Hemingway, a couple of mashers in a bar have stepped out of a Miller Lite audition, and Jessica’s blind dates are freakish in their misplaced male vanity. No wonder we don’t stand a chance against perceptive, high-spirited Helen.) But the toughest assignment goes to Tovah Feldshuh, who plays Jessica’s mother. Through the first two-thirds of the film she’s a cringe-inducing composite of every Yiddishe mama to ever hit the big screen: pushy, meddlesome, blind to the fact that her own anxious vigil on the subject is what keeps her daughter single. Then, suddenly, Feldshuh is given the loveliest moment in the film. I won’t give it away, but the mask-like grimace falls away, revealing more than cartoon recrimination.
Jessica’s here, she’s queer, but don’t necessarily get used to it: The movie endorses a casual indifference to identity sloganeering, and nobody, Helen included, exactly comes roaring out of the closet. For better and for worse, this is not a movie about painful choices or necessary allegiances. What the amitié amoureuse with Helen has given Jessica, we’re meant to believe, is courage, though it feels a little like a makeover: She lets her hair kink out, drops her job as a copy editor, and pursues her talent as a painter. As we’re kissing Jessica Stein goodbye, the two sit together, gossiping, and it’s hard not to feel we’ve been treated to a refreshingly dorky and humane little film.
But it raises the question of how much grade inflation the scrappy first-time feature still merits. While Jessica and Helen fight it out in the street, passers-by stop and stare. We know these pedestrians are simply enchanted by the lights, the hubbub, and the handheld camera, but our disbelief stays pleasantly suspended: They could just as easily be gawking at the newbie lesbians, learning to scream at one another in the street. It’s a nice moment—these random bystanders are the guerrilla filmmaking equivalent of extras—and it disposes us toward the film. Nonetheless, now that we’ve eaten Raoul, chased Amy, boxed Helena, drowned Mona, been John Malkovich, and for God’s sake, felt Minnesota, our sympathy for the gerund-entitled, under-budgeted movie is, to say the least, no longer automatic. Kissing Jessica Stein is smoothly narrated and is packed with some wonderful quirks. Nonetheless, it could have taken more to heart the lovely paradox it reserves for Jessica: that we most become ourselves in our capacity to surprise ourselves. It’s a sign of respect to want this film to have been more original in some of its particulars.