Kissing Jessica Stein ends several times — which likely explains how a film with so short a running time, 96 minutes, feels as though it lasts much longer — and each conclusion satisfies; each feels real, natural, and best of all, inevitable. That is, except for the actual finale, which so betrays what's come before it that it leaves one walking out of the theater holding a grudge against what was, until its final few minutes, a slight but affable piffle of a film. (At its worst, it resembles an overlong pilot for a new NBC series — think Leap of Faith.) Perhaps some wise theater programmer will one day schedule Kissing Jessica Stein on a double bill with Kevin Smith's equally frustrating and ragged Chasing Amy, in which a straight man “converts” a lesbian who'd written off men; arguments for and against both films could fill a special issue of The Advocate. I suspect all but the same-sex hobbyist would find a lot wrong with both movies, which submit that sexuality is merely a choice — a diversion for dilettantes.
Neither movie bears the strength of its convictions; they're romantic comedies in name only, without the slightest hint of romance aside from the plot setup they've provided us. That they're conflicted — Kissing Jessica Stein, ironically, takes forever just to build to a peck on the cheek — may in fact be an honest reflection of the filmmakers' own desires and tastes, but they send such weak signals you may have trouble picking them up at all. 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 and insight and empathy — quickly dissipates.
In all of Manhattan, Lisa Kudrow look- 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 copy editor 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, a sentiment reinforced by her overbearing but ultimately empathetic Jewish mother (played by an overexcited Tovah Feldshuh), who tries to convince her daughter to date any man wearing a yarmulke.
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 reception. The conventions of romantic comedies lead us to assume it's only a matter of time until the two reconnect. They bicker and banter like an off-Broadway Cary Grant and Rosalind Russell; Jessica will be Josh's girl Friday on Saturdays and Sundays 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 string 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 of the penis; she's seeking an escape, perhaps temporary or maybe permanent, from the ol' in-and-out. 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 split 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 develop into a long-lasting attraction, or is it merely a passing fancy, a detour for two girls sick of boys?
Westfeldt and Juergensen — who together 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 witty banter, gives the film its warm center; their off-screen relationship gives depth and resonance to what unfolds on screen. Jessica's initially reluctant to engage in a sexual relationship with Helen; the best scenes are those in which she can barely stand to kiss Helen, much less do anything more with her. She treats her less like a lover than like a friend. She's conflicted and ashamed, a good Jewish girl riddled with guilt (which proves pointless, since hers is a surprisingly understanding family).
Eventually, Jessica and Helen settle into a comfortable routine, and 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 (he most recently helmed the Facts of Life TV reunion pic), felt straights would be so off-put 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 then give us, in its stead, a movie you want only to kiss off.