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Kissing Jessica Stein [DVD]

Director : Charles Herman-Wurmfeld

Screenplay : Heather Juergensen & Jennifer Westfeldt

MPAA Rating : R

Year of Release : 2002

Stars : Jennifer Westfeldt (Jessica Stein), Heather Juergensen (Helen Cooper), Scott Cohen (Josh Myers), Jackie Hoffman (Joan), Tovah Feldshuh (Judy Stein), Robert Ari (Sidney Stein), David Aaron Baker (Dan Stein)

Kissing Jessica Stein is about two women who decide to try lesbianism for completely different reasons. The eponymous Jessica (Jennifer Westfeldt) decides to give it a try because she has all but given up on finding Mr. Right—her latest series of dates has ranged from a smarmy lounge lizard to an egghead accountant whose idea of going dutch means itemizing everything down to who ate the more expensive leaves of lettuce in the salad. On a fluke, she answers a woman-seeking-woman personal ad placed by Helen Cooper (Heather Juergensen), a confident sexual adventuress who desires to go bi just because it's something she hasn't tried before. In other words, the two couldn't be any different.

The material in Kissing Jessica Stein is tricky, dealing as it does with the fluidity of sexuality within the usually rigidly heterosexual confines of the romantic comedy. The reason the movie works as well as it does is because the two leads have a deep understanding of their characters and bring to their roles both an infectious charm and an underlying conviction to everything they do. It also helps that the movie is quite often very funny—not always laugh out loud funny, but funny in a recognizable "that's life" kind of way. Remove the lesbianism, and the intimate scenes between Jessica and Helen are just like fumbling teenagers tentatively and excitedly discovering each other for the first time. Of course, in such situations, one person is often more enthusiastic than the other, which is also the case here. Helen has long since made up her mind that she can go both ways, but Jessica is unsure, which causes her to go so slowly that Helen complains at one point that she's dating "a Jewish Sandra Dee."

The story is set in the hustle and bustle of New York City, where Jessica is a copy editor for a newspaper and Helen is the director of an art gallery. Their respective professions fit them like a glove, as Jessica is a borderline-neurotic perfectionist whose exacting tendencies have made it that much more difficult for her to find happiness with a significant other, while Helen is confident and assured, willing to try something new for the simple sake of its newness. Where Jessica is uncertain, Helen is bold.

What is surprising to both of them—and ultimately to us in the audience—is how perfectly matched they end up being. To the astonishment of both Jessica and Helen, they end up falling in love—the fling with lesbianism develops into a genuine opportunity for a meaningful relationship. Partly, it is because they are both women, and they connect on the levels of taste in fashion and literature in a way that the men in their lives are incapable of (one of the best scenes in the movie has them in the back of a taxi cab discussing techniques for blending lipstick colors). Yet, it is also their opposite-ness that makes them work so well together, with Helen bringing Jessica out of her perfectionist shell and Jessica showing Helen that not rushing into things can sometimes make them that much sweeter.

There are complications, of course. While Helen is loud and proud about her decision to switch teams, Jessica is more unsure, deciding instead to hide the fact that she is involved with a woman. She is especially intent on hiding it from Josh (Scott Cohen), her ex-college-boyfriend and current boss. Josh is clearly unhappy in life and tends to take it out on Jessica in passive-aggressive bursts (he only refers to her as "Stein," a clear distancing technique that clues us in right away that he is still pining for her). She also keeps her new relationship from her meddling mother (Tovah Feldshuh), who is deeply concerned that her daughter is 28 and still not married, and thus attempts to set her up with every eligible Jewish bachelor who's willing to come over for dinner.

In addition to being a funny and intimate comedy, Kissing Jessica Stein is also a rare outsider success story in Hollywood. The two stars, who became friends during a theater workshop in 1997, developed it first as an off-Broadway play called Lipschtick and then turned it into a script that they shopped around, eventually securing enough financing to make it a go. It is to director Charles Herman-Wurmfeld's credit that he keeps the emotional comedy and energy of the more intimate theater setting while also expanding the story visually, particularly in his use of constantly moving handheld cameras and real New York locations. Kissing Jessica Stein has a texture that belies its low budget.

It's sweet and funny and often very clever the same vein as Woody Allen's neurotic romances, but most of all it grabs you with its honesty—you can believe in the way the characters respond to the situations. There is humor to be found in two women exploring an aspect of sexuality they had not previously considered, but what sells the story is that it finds the emotional core behind the sex. Most women (or men, for that matter) probably won't follow the path Jessica Stein follows in order to find her true self, but we can all recognize the urges behind it.

Copyright © 2002 James Kendrick