"I'm a pretty self-defecating guy," a would-be knight in shining armor tells the battle-weary heroine of Kissing Jessica Stein in one of those blind-dates-from-hell montages. Most of us would die laughing if we heard such a line. Jessica (Jennifer Westfeldt) merely cringes, because 1) she's a copy editor for whom words are everything, 2) she's tired as hell of men who have neither hearts nor brains, just courage, 3) she's rather picky and 4) she's rather neurotic. A Sapphic Annie Hall, Kissing Jessica Stein sends our "Jewish Sandra Dee" into the arms of Helen (Heather Juergensen), an art-gallery director who'll take a fling no matter who's flung it. And together, these contemporary cuties add a few new wrinkles to the old romantic-comedy genre. Lovers? Friends? Roommates? You sort it out.
Or tag along as Jessica and Helen, neither of them a card-carrying lesbian, sort it out. Written by the actresses playing the two leads, Kissing Jessica Stein is that rare thing, a literate movie about literate people. When I saw Jessica's apartment, which is crammed with books, I thought I'd died and gone to heaven. And if the filmmakers overdo it by giving the place a spiral staircase, they steer their semi-independent film away from the mainstream by immersing us in Jessica's Jewish friends and family. The movie opens with Jessica's mother (given the full "Coffee Talk" treatment by Tovah Feldshuh) trying to scrounge up a date for Jessica during the services at a Scarsdale synagogue. And as Jessica's co-worker and friend Joan, Jackie Hoffman manages to evoke both Fran Lebowitz and Gilbert Gottfried.
Although it includes the obligatory scene of two heterosexual men detailing why it's so damn sexy whenever two women get in bed together, Kissing Jessica Stein does a nice job of tracking the way the heart, the brain and the libido can send you first one way, then the other, especially if you're a woman. In Jessica's case, perhaps it's more the heart and brain, less the libido. So squeamish is she in the early going that she and Helen give each other a high-five after their first semi-successful kiss. Some may resist Westfeldt's Diane-Keaton-by-way-of-Lisa-Kudrow number. Others will find her irresistible, making it that much harder to bear when the movie suddenly deepens and becomes about something more than Jessica's choice of partners. A phase? A lifestyle? An identity? The movie comes up with all sorts of reasons for kissing Jessica Stein.