Kissing Jessica Stein

Like the heroine of its title, Kissing Jessica Stein is slight but (slightly) charming.

Think of it as When Harry Met Sally in reverse, a sugar-coated rom-com about two people who try to find true love together and wind up as true friends instead. The twist, as you probably know by now, is that the two are women.

Jessica (Jennifer Westfeldt) is the prototypical single New Yorker in her late twenties. She’s pretty, bright, opinionated, neurotic, and underemployed, working as a copy editor at a New York City newspaper. She has all but given up on dating, and most of her friendships revolve around work, where she confides in a supportive but clever coworker (the kind of role Eve Arden used to play) and trades barbs with her dour but handsome boss and ex-boyfriend, Josh Meyers (Scott Cohen).

One day, on a whim, Jessica answers a personal ad under “women seeking women” and meets Helen (Heather Juergensen), the beautiful, stylish manager of a Chelsea art gallery. Although Helen, too, has only dated men, she pursues the skittish Jessica, who is attracted in spite of herself.

Westfeldt and Juergensen, hetero friends who co-wrote the script, play this budding romance convincingly. Their breathy, excited voices on the phone to each other when they’re making a date convey all the excitement of a new romance, and there’s real heat in some of their early makeout scenes. Westfeldt, who has the healthy good looks of a somewhat less angular Jennifer Aniston, can look merely pretty or incandescently beautiful. Her Jessica begins to glow as she and Helen progress (too slowly for Helen’s taste) from discussing lipstick, clothes, and men to carefully choreographed, painfully self-conscious makeout sessions to a full-blown, tender love affair.

Kissing Jessica Stein often crosses the line between clever and glib, as in a mostly wordless collage showing Jessica and Helen moving in together, giggling and squealing like Britney Spears fans. Its attempts to plumb its characters’ creative depths can be painfully shallow as well. Bad enough that we’re meant to believe that Jessica creates brilliant artwork—a conceit so unlikely that several characters comment on how improbable it is. But credibility is bent to the breaking point when, after seeing one of Jennifer’s canvases in Helen’s gallery, Josh is inspired to return to his neglected writing in a night-long flurry of typing that leaves him transformed, almost giddy.

The movie also misses the mark when, after having jackhammered home the notion that Josh and Jessica are meant for each other, it leaves their stop-and-start courtship unresolved. Helen is given a happy ending, but Jessica’s romantic fate remains unknown. That’s not to say happy-ending conventions must never be broken, but this movie is too light to support an ambiguous ending.

But this is an enjoyable date movie for people who don’t get militant about other people’s sexual preferences, with sometimes snappy dialogue and plenty of brief bits skewering various forms of smarm and self-delusion. During a montage of disastrous dates, one man smugly describes himself to Jessica as a “self-defecating guy,” while another purrs: “I like the way your hair goes around your head like that.”

The main joke is that everyone else in the movie handles Jessica’s initiation into gay sex better than she does. Not everyone reacts sensitively—a gaggle of curious older women pepper Helen with boorish questions at a wedding, and two men who try to pick up Jessica and Helen at a bar jabber on about how lesbian sex is “double sexy.” But the only person to openly disapprove of their relationship is a gay male friend of Helen’s, who is offended by what he thinks is her trendy, superficial experimentation with lesbianism.

Even Jessica’s mother (played by the wonderful Tovah Feldshuh) handles her daughter’s foray into lesbianism better than Jessica herself does. After seeming oblivious to the affair for months, she gently and lovingly brings it up when Jessica is afraid to, in a scene that brought unexpected tears to my eyes. In that scene and others, Feldshuh transforms what could have been a stereotypical Jewish mother role, revealing the sense and sensibility beneath her character’s meddling surface.

written for TimeOFF