The only real difference between "Kissing Jessica Stein" and any of the other New York-centric romantic comedies that have followed in the wake of Woody Allen is its same-sex storyline.
Perhaps that's a bit unfair to this low-key character piece, which does have some modest charms and at least one or two big laughs. And it's not as sex-obsessed as so many other gay comedies seem to be. (It's refreshing that, even though it was directed by a man, this "girl-meets-girl" story is not as exploitative as you might expect.)
Still, it's pretty lightweight fare that doesn't really resonate or linger in the memory, and its ending is entirely too predictable for its own good. And, unfortunately, the title character (played by Jennifer Westfeldt, who also co-wrote the script) may be the least appealing and interesting person in the film.
She's a New York copy editor who rejects nearly every man she meets, because, as she tells its, they're all "freaks and morons." So to her surprise, she finds herself answering a "women seeking women" ad in the Village Voice. But she's barely able to exchange more than a couple of words with the ad's author, Helen Cooper, an art gallery director who has also had it with men (Heather Juergensen, the other co-scripter).
Still, Helen persists, and the two find themselves hitting it off even if Jessica tends to overthink the burgeoning relationship and attempts to conceal it from her mother (a scene-stealing Tovah Feldshuh). There's another possible complication Jessica's boss and ex, Josh (Scott Cohen), who is constantly sparring with her at work but who still seems to have some strong feelings for her.
Again, it's pretty obvious where all of this is going. Fortunately, director Charles Herman-Wurmfeld keeps things moving at a pretty breezy pace, and some of the casual observations on modern-day dating are amusing.
But it's still up to Westfeldt to make us like Jessica and believe her character's quirky story arc, and in that regard, she fails. (She also never looks comfortable in the more intimate scenes with Juergensen.) On the other hand, Juergensen is a fresh face, and as Helen, she's so likable that you sort of wish the whole film had been built around her instead.
"Kissing Jessica Stein" is rated R for vulgar sexual talk and use of crude sexual slang terms, occasional use of strong sexual profanity, simulated sex (fairly discreet) and brief drug content (use of prescription drugs). Running time: 96 minutes.