Heather Juergensen, Jennifer Westfeldt, ...
Credit: Kissing Jessica Stein: Hope Wurmfeld

The sitcom-style romantic comedy Kissing Jessica Stein gets right to the root cause of Jessica’s romantic afflictions. As the story opens, we see the title heroine (Jennifer Westfeldt) — a pretty, single Jewish woman who appears to be in her late twenties or early thirties — sitting with her mother and grandmother in a Scarsdale synagogue where prayer and reflection are low on the agenda. While the rabbi expounds and Jessica squirms, her mother (Tovah Feldshuh) catalogs various Jewish men with whom she has tried to match her picky daughter. All, apparently, are too dull, or average, or balding, or otherwise defective to meet Jessica’s standards — and Grandma’s. ”No sex appeal,” cackles the old lady, who has evidently watched too many repeats of ”The Golden Girls.”

Ah, so this is how it is: Neurotic Jewish heroine (a journalist, for fashion’s sake, at a hip New York weekly newspaper) from a family of yentas seeks Jerry Seinfeld/Mr. Big/Mr. Darcy look-alike for amusing quips, misunderstandings, situational laughs, and snazzy Dwell magazine set decoration. But no. ”Kissing Jessica Stein” then takes a ”Sex and the City” turn: In flibbertigibbety frustration exacerbated by the happiness of family and friends around her — brother engaged to a Nice Jewish Girl, office friend finally pregnant — Jessica decides to try dating a woman. So she answers a personal ad. She meets Helen (Heather Juergensen), a similarly slim, pretty, groovily dressed, plugged-in gallery owner also looking to double her romantic options. The two women stumble and giggle as probationary lesbians. And some hilarity ensues, padded out with useful conversation about lipstick application.

Cute? Sure, why not: Who wouldn’t enjoy snappy conversations between attractive women about how to do that thing that Sapphists do. Trendy? Probably more than Juergensen and Westfeldt, who wrote their screenplay based on their 1997 Off Off Broadway ”Lipschtick,” could have known, what with everyone coming out Rosie these days. Insightful? Maybe about cosmetics, and the relative elasticity of female sexual identity, the way some women can go girl-girl (to the excitement of some men) and then come back to men unencumbered by gay or straight labels (to the excitement of Coley Laffoon).

But if I waver in my enthusiasm, less than easily charmed by a movie trying so cheerfully to entertain (hey, lady, lighten up!), it’s because ”Kissing Jessica Stein” is all too content to be a comedy of surfaces and stereotypes. And because, for all the novelty of the bisexual romantic angle, there’s something about Jessica, her New York-singleton ticks and her Jewish-family tocks, that feels…old.

Possibly even as old as 1977, when ”Annie Hall” set the movie blueprint for smart-ditz urban single girls in the modern age. Certainly, Westfeldt ought to be paying royalties to Diane Keaton for such generous appropriation of Keaton’s influential mannerisms — the la-di-da fluttering and stuttering, the Gee, no, I can’t, can I? insecurity. We accept that Jessica is interested in a relationship with another woman because she says she is, but there’s nothing in the self-conscious performance to suggest that Jessica is really interested in anyone — not in Helen; not in her editor and college boyfriend, Josh (Scott Cohen), a standard-issue commitmentphobe who’s got his own case of ”Anything but Love” itchies; not in her family, either.

She’s dull! As directed by feature first-timer Charles Herman-Wurmfeld with all the inventive use of on-the-fly location shooting a low budget could muster, this Jessica is a dull part-time lesbian and full-time ditherer!

It’s her mother who’s interesting. In the past decade or so, Tovah Feldshuh has taken a lot of roles in the category defined by dramaturges and Yiddishists as baleboosteh — part peerless homemaker, part professional ball of fire — in characters ranging from high-powered defense attorney on ”Law & Order” to Catskill mama in ”A Walk on the Moon.” But I’ve never seen Feldshuh steal the show so completely and definitively as in one scene in ”Kissing Jessica Stein” where the Jewish-mama act is dropped and real loving connection takes place between mother and daughter. It’s a scene so unlike any other in this skim-decaf-cappucino cup of cinema that it actually throws the rest of the movie into disarray — a scene in which an older actress says, ”Okay, girls, you’ve got the frothy lines, but I’ll show you some hot stuff.”

At that moment, by the way, the very shape of the Stein Chronicles shifts, because there’s so little of the opening scene’s cartoonish matchmaking noodge in this depiction of an ideal mother who could be so sensitive to her daughter’s emotional needs. At that moment, too, the daughter gives up wifty, scatterbrained, childish things and becomes a far more appealing grown-up. The dramatic possibilities are tantalizing. And ignored. After that moment, ”Kissing Jessica Stein” returns to the regularly scheduled program already in progress.

Kissing Jessica Stein
  • Movie
  • 96 minutes