Where Jessica Stein could have been brave and daring, it's instead cowardly -- too coy to make good on its promise, too chickenshit to deliver the goods. Whatever good will it engenders -- and it's a great deal, because these are likable people uttering witty things full of clarity, insight, and empathy -- quickly dissipates.
In all of Manhattan, Lisa Kudrow look-alike and sound-alike Jessica Stein, played by Jennifer Westfeldt, can find only slimy narcissists, nerdy cheapskates, and Jim J. Bullock in the shallow dating pool. When Jessica, a copyeditor at an unnamed New York newspaper who fills her lonely hours painting canvases in her tiny but well-appointed apartment, does find a man with whom she can converse -- and at whom she can stare -- he is, of course, taken. The 28-year-old Jessica figures, as all overly dramatic single 28-year-olds are wont to do, that love, or a shot at it, has left her behind.
The only guy with whom Jessica has any kind of relationship is her editor and ex-boyfriend, Josh (Scott Cohen), who dishes out tsuris like a waiter at a bar mitzvah buffet. The conventions of romantic comedies lead us to assume it's only a matter of time before the two reconnect. They bicker and banter like an off-Broadway Cary Grant and Rosalind Russell; Jessica will be Josh's girl Friday. Saturday and Sunday as well.
On the other end of town and at the other end of the spectrum is Helen Cooper (Heather Juergensen), an art-gallery owner with too many options. Hers is a litany of eager-to-please boyfriends, a buffet of lovers from which she chooses depending upon mood and urge. She's Jessica's antithesis in every way -- adventurous, ravenous, interesting. And unlike Jessica, Helen is bored with the penis; she's seeking an escape, perhaps temporary or maybe permanent, from the ol' bump and grind. She places a personal ad in the "Women Seeking Women" section of the Village Voice; little does she suspect her bait will lure an amateur, a straight woman so desperate for love, she'll try anything. Sort of.
Helen and Jessica share one thing -- a passion for the florid poetry of Rainer Maria Rilke -- but before long, they share a kiss, a bed, an apartment, and a relationship built, at least at first, out of curiosity. Two straight women find love in each other's "thin arms," as Jessica likes to say. The question, then, becomes: Is theirs to become a long-lasting attraction, or is it merely a passing fancy -- a detour for two girls sick of boys?
Westfeldt and Juergensen -- who wrote Kissing Jessica Stein and its stage-play predecessor, Lipshtick -- make for a likable couple. They possess a natural chemistry, even if it's like dry ice dipped in warm water, creating less smoke than vapor that quickly dissipates. Their relationship and their warm and witty banter give the film its center; their off-screen relationship gives depth and resonance to what unfolds on-screen.
Eventually, Jessica and Helen settle into a routine; theirs becomes an almost passionate relationship, against Jessica's better judgment. But just as suddenly as curiosity turns to ardor, the film abruptly betrays its better instincts by giving us the predictable, pat ending. It's as though Westfeldt and Juergensen, whose script was directed by Charles Herman-Wurmfeld (who most recently helmed the Facts of Life TV reunion pic), felt straights would be so put off by the possibility of a happily-ever-after for two newbie lesbians that they couldn't stand the thought of sacrificing a single ticket sale. So they tease us with a charming, damned near revolutionary little film about love and give us, in its stead, a movie you want only to kiss off.