Some moviegoers may feel similarly about romantic comedies: Why are brains, wit and a lack of ugliness so rarely part of the same package?
Like Ben Affleck and Matt Damon with "Good Will Hunting," co-stars Heather Juergensen and Jennifer Westfeldt wrote "Kissing Jessica Stein" as a way to get themselves better roles than they were (or weren't) being offered. Westfeldt plays the title character, a neurotic Jewish New York newspaper copy editor who manages to stand apart from the various other neurotic Jewish New Yorkers we've seen on film.
Lack of spontaneity
In slender build and nervous energy, Westfeldt suggests a Lisa Kudrow type, but Jessica's flakiness is rooted in too much -- rather than not enough -- thinking: She's so compulsively rational that she stifles any spontaneous feelings.
Juergensen's Helen Cooper, an outgoing Soho art gallery manager, has no such fears of impulsiveness. Helen, whose features are as full as Jessica's are fine, is casually juggling three male lovers but feels a void. So she takes out a woman-to-woman personal ad that Jessica, in a rare quick-reflex reaction, answers, the selling point being a Rilke quote about opening oneself up to possibilities.
Helen is chagrined that on her maiden adventure on the other side of the fence, she winds up with "the Jewish Sandra Dee," who assumes that Helen is an experienced lesbian.
Much of the humor of "Kissing Jessica Stein" lies in these two likable, odd-couplish women trying to construct a relationship from scratch. While Helen is gung-ho to get to the physical side of things, Jessica is busy studying lesbian-sex pamphlets and studying Helen's method of blending lipsticks.
The movie has its broader gags, too, some that score -- such as Jessica's mom (Tovah Feldshuh) and grandmother (Esther Wurmfeld) conspicuously scoping out the Yom Kippur service crowd for potential Jessica fix-ups -- and some that cover overly familiar ground -- such as the parade of capital-L Loser dates that Jessica must endure before meeting Helen.
But what enables "Kissing Jessica Stein" to overcome its awkward moments and ragged patches is its truthfulness. Westfeldt and Juergensen have written and portrayed these characters with a high level of specificity. Helen may be the less fleshed-out of the two, but we get a real sense of her world and a restlessness that is borne less of frustration than an eagerness to experience more.
The relatively repressed Jessica directs her passion toward words; she suffers the frequent misuse of "nonplussed" and initially likes Helen for her creative application of "marinate" in a non-food context.
Westfeldt shows a keen sense of comic timing as a jittery Jessica explains why she couldn't do yoga and protests that she is "too me" to carry on a lesbian relationship. But the actress never turns Jessica's neuroses into shtick. When an exasperated Helen asks her, "What do you do to be happy?" Jessica's quick answer -- "I'm not" -- is both funny and painfully true.
Likewise, despite the soundtrack's requisite swing tunes meant to lend an old-fashioned air, the movie explores the nature of relationships with 21st Century complexity. The question isn't whether Jessica and Helen will get together but whether what they have -- love, friendship, shared humor -- is enough to sustain them.
Relatively unseasoned director Charles Herman-Wurmfeld is a straightforward storyteller who keeps the camera intimate and inconspicuous; he feels no need to distract us with flashy camerawork.
He and his writer-stars display much affection for the supporting characters, and the performers follow suit. Feldshuh's Jewish mom is never as overbearing as loving, and she's given an especially potent secret-revealing scene with Jessica.
Abrasive yet sympathetic
Jessica's editor and one-time college boyfriend, Josh Meyers, grows in dimension throughout the story as Scott Cohen plays him with the right mixture of abrasiveness and sympathy. Meanwhile, Jackie Hoffman does the best-friend role proud as Joan, Jessica's pregnant buddy who has a way of opening her mouth really wide to express astonishment.
The lesbian content may titillate some and scare off others -- though the movie shows nothing more graphic than kissing -- but that's not really what "Kissing Jessica Stein" is about. It's about the need to take a daring leap to discover who you truly are.
Various characters see their risk-taking open up new possibilities. The same might be said of Westfeldt and Juergensen, who should reap the rewards of having thrown their considerable energies into the perilous indie film world and emerged with an engaging, original work. When life doesn't hand you a dream date, sometimes you've got to create your own.
3 1/2 stars
"Kissing Jessica Stein"
Directed by Charles Herman-Wurmfeld; written by Heather Juergensen, Jennifer Westfeldt; photographed by Lawrence Sher; edited by Kristy Jacobs Maslin, Greg Tillman; production designed by Charlotte Bourke; music by Marcelo Zarvos; produced by Eden H. Wurmfeld, Brad Zions. A Fox Searchlight Pictures release; opens Friday. Running time: 1:36. MPAA rating: R (sexual content, language).
Jessica Stein.....Jennifer Westfeldt
Helen Cooper.....Heather Juergensen
Josh Meyers.....Scott Cohen
Martin.....Michael Mastro Sebastian.....Carson Elrod
Mark Caro is the Chicago Tribune movie reporter.