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The Complicated World of Women’s Relationships

The surprising thing about the film “Kissing Jessica Stein” is just how many different people find it “cute”: lesbian couples, men and women, even my parents.

While “Kissing Jessica Stein” sports the structure of a conventional love story—in this case, girl meets girl with some obstacles along the way—it’s ultimately a charming exploration of one woman’s stumbling quest toward happiness. The dialogue is literate, the acting invests the characters with depth, its humor strikes the right note between caricature and authenticity, and the cinematography shows off the New York that New Yorkers love.

Like Woody Allen’s protagonists, Jennifer Westfeldt’s Jessica Stein is funny, neurotic, smart, and Jewish. At 28, Stein is worried that she’ll be alone forever. Her dates with men start out promising but end up disastrous; the men all turn out to be hitched, gay or ugly. Helen Cooper (Heather Juergenson) is a sex-crazed downtown hipster, an assistant director at a Chelsea art gallery who juggles boyfriends but feels unsatisfied. On a whim, Helen places a woman-seeking-woman ad, and, on a whim, Jessica replies. The movie moves through some hilarious scenes as Jessica attempts to back out of the relationship even as she’s falling for Helen. Throw in the tension of an ex-boyfriend/current boss, a matchmaking Jewish mom from Scarsdale, and an inquiring office-mate, and you have Jessica Stein’s life.

Westfeldt and Juergenson make a striking couple. They play a pair of girly-girl lesbians (in one scene, they actually enjoy a lengthy discussion about lipstick) with an undeniable chemistry. hi fact, everyone in the movie is good-looking, which is part of what makes “Kissing Jessica Stein” eminently watchable. The movie goes to pains not to offend, to make sure that there’s something and someone for everyone. There’s no on-screen sex in “Kissing Jessica Stein”. Just a lot of, well, kissing. And no one on the screen seems to balk too much at these straight-girls-turnedlesbians. Even Jessica’s mother, played by the gifted Tovah Feldshuh, embraces Jessica’s choice without angst.

The success of “Kissing Jessica Stein” lies partly in the fact that Juergenson and Westfeld co-wrote the screenplay they’ve been developing since 1997, when its first incarnation, Lipschtick, played Off-Off Broadway.

“Kissing Jessica Stein” does not market itself as Jewish or lesbian but as “a fresh take on the subject of sex and the single girl.” Critics have described it as a “hot date movie,” and have called it the 21st-century version of “Annie Hall.” I would argue it fits more firmly into the mold of gay ethnic comedy like “The Wedding Banquet” or even into a social comedy of errors, a la Jane Austen, with the Jewish content obvious from the opening High Holiday scene. And though the word “lesbian” is uttered only two or three times, there is plenty of posturing over what it really means today to date someone of the same sex.

One of Helen’s gay friends chides her for believing she can choose to be a lesbian, tutting “Today, sexual preference. Tomorrow, henna tattoos,” and insists that you’re born gay the way you’re born black. Another friend disagrees, pointing out that “An orgasm is an orgasm.” In one of the funniest scenes in the movie, Helen pushes aside Jessica’s “informational materials” about lesbian sex toys. When Jessica fails to understand how lesbian sex can be like straight sex, Helen declares, “Let’s face it; it’s the other stuff that works for women anyway.”

While some Jews may thrill to the outcome (with its hint of continuity), others in the audience will be disappointed. They may judge the entire movie to have been barrelling toward a traditional ending, while the rest of the story was a mere diversion. But it would be a mistake to dismiss the movie. Take “Kissing Jessica Stein” on its own terms—as the story of one rigid woman’s transformation into a looser and, ultimately, happier person— and Westfeldt’s expressive face and acerbic wit will have you laughing and crying along with her.

Rebecca Metzger is a freelance writer, arts publicist and poet, living in Brooklyn.