Fell In Love with a Girl: KISSING JESSICA STEIN

If Woody Allen in his prime had made a lesbian romantic comedy that avoided the usual Woody neuroses and verbal tics while remaining immensely funny and likable, it would be pretty close to Kissing Jessica Stein—that is, a valentine to love, New York City, and old jazz tunes, only with two girls kissing. Cowritten and produced by its stars, Jennifer Westfeldt and Heather Juergensen, the film was a hit on the indie and festival circuits back in 2001 and remains the perfect antidote for anyone feeling nutrient-deprived by the formulaic slop served up with the likes of Kate Hudson, J-Lo, and Katherine Heigl (whose three names in succession summon up in me a kind of indigestion of the soul).

Juergensen and Westfeldt

But calling Kissing Jessica Stein a lesbian romantic comedy isn't entirely accurate, since both the main characters start out straight and with only a bout of bicuriosity. Westfeldt plays Jessica, a magazine editor and self-described "Jew from Scarsdale" who's a hyper-articulate Diane Keaton/Lisa Kudrow type with standards for men as exacting as her standards for words. When, after a dispiriting series of blind dates, her attention is drawn to a personals ad quoting Rilke (her favorite writer), she finds herself intrigued even though the quoter is a woman. That woman, a free-spirited art gallery director named Helen Cooper (Juergensen), has grown fed up with the hairier sex and wants to try the other side of the fence for a change.

Jon Hamm in a brief, early role

On their first date together—which Jessica repeatedly tries to abort—Helen senses the spark between them and does everything she can to help Jessica through her skittishness. This eventually requires a Job-like level of patience as Helen indulges Stein's increasingly comic attempts to grapple with the mechanics of a Sapphic union. "I took out an ad, for Christ's sake," she complains to friends, "and I ended up with the Jewish Sandra Dee! What are the odds?" When the deed is finally done (in the least likely of settings), Jessica is amazed to find herself in the relationship she's always dreamed of, minus the expected testosterone.

With such barriers as class, wealth, race, and reputation mostly irrelevant in modern romantic comedy, Kissing Jessica Stein finds its conflict in the 21st-century obstacle of sexual preference. For despite how perfect the two women seem together, their relationship is threatened by Jessica's fear of making their private life public—what will her family and friends think?—as well as her own ambivalence toward dating a woman. At the same time her boss, a college ex played with simmering self-loathing by Scott Cohen, finds himself intrigued by this newer, happier Stein, even if he, like everyone else, has no idea Jessica's new beau is a belle. Complications, as expected, ensue, as do some surprisingly emotional moments, including one standout with Tovah Feldshuh as Jessica's mom (tears will be jerked).

Yes, Mom, we'll behave

Produced on a budget of shoelaces, old bottle caps, and loads of called-in favors, Kissing Jessica Stein uses its literate, emotionally truthful script, sharp dialogue ("Who do I have to blow to get some pussy around here?"), and well-realized characters to deliver the perfect example of a "scrappy indie" with all the earmarks of a traditional romantic comedy. The names and faces may be unfamiliar (aside from Feldshuh and a then-unknown Jon Hamm), but nothing here feels forced or like kids playing dress-up. Westfeldt and Juergensen knew their genre well when writing (and performing) these parts, and nearly always find a way to embrace the spirit of a cliche without being hamstrung by its predictability.

Certainly the premise of the film is less of a novelty now, 12 years later, but what keeps Kissing Jessica Stein fresh—and above the level of a sitcom—is its lively, off-center performances, verbal wit, and an infectious generosity of spirit. The two women—along with director Charles Herman-Wurmfeld—play fair with the film's characters, giving each a believable mix of virtues and flaws (including most of the men). Is it politically correct and 100% Gay Community Approved? I'm not one to say. But with its comforting, old-fashioned soundtrack, sharp cinematography, and the undeniable chemistry between its leads, it's a film even a young Woody would be proud of. Especially the girls kissing part.