Kissing Jessica Stein

“Sometimes, I think I’m gonna be alone forever.” Jessica’s fear strikes at the sensitive core of single women everywhere, and so does Kissing Jessica Stein with its natural, hip and aware perspective into the tragedies and unpredictable rewards of the search for love. Jessica Stein is 30-ish, beautiful, smart, successful, talented, neurotic and lonely because her expectations exceed what the dating pool has to offer — and as we single girls know, it’s a sad, sad hetero-sea of “unacceptables” out there, even in Manhattan.

Jessica hasn’t dated in a year. She works with her bitter ex-boyfriend Josh and her best friend who’s married and very pregnant. But the straw that snaps her into action is when her brother gets engaged to be married. The result is a painful string of “nowhere” dates that trudge through good-looking and disturbingly self-absorbed to boring, nerdy and cheap to borderline gay — all miserable failures and strikeouts that seem to seal her fate as an upward, professional spinster.

And then there’s Helen: a hot, art-gallery girl with many men at her disposal, but no “one” who really satisfies all of her needs (hunger, boredom and horniness) at once. At this point, she’s willing to try girls — so with the help of her gay friends who pick out a juicy Rilke quote for her personal ad, she sends the message out in the “Women Seeking Women” section, which Jessica’s co-workers accidentally read to her. Even though they realize their mistake immediately, the bra is snapped because Jessica had just been reading the very same Rilke words, and synchronicity is too powerful a force to be ignored.

How refreshing it is to listen to dialogue that’s very clever, very funny and very realistic, spoken from the mouths of actors who convey the same attributes. Chances are you won’t recognize most of these relatively obscure thespians, but their characters come off as comfortable as close friends, not even breaking a sweat with all the undercurrents of subtext they have to carry.

Jennifer Westfeldt and Heather Juergensen not only star in the film as Jessica and Helen, they produced it and wrote the script as well, developed from their 1997 play Lipschtick (undoubtedly derived from a passing lipstick metaphor between the girls, in which Helen explains how she blends three shades of lipstick to get that perfect color, and Jessica admits she’s just looking for that one perfect shade). Their talents are multileveled, like their screenplay, characters and acting abilities, and I’ll bet these girls really do have trouble finding guys who interest and challenge them.

Charles Herman-Wurmfeld, whose only previous claim to fame was directing “The Facts of Life Reunion” for TV, directed the film, and aside from a couple of sticky and questionable camera-shot choices, he manages to space, pace, unfold and develop this happening that rings true, considering today’s atmosphere of acceptable sexual exploits. Nowadays, it’s not unheard of to see normally heterosexual women turn to other women for relationship satisfaction; whether it’s out of frustration, an attraction or simply experimentation is a toss-up. Regardless of the reasons, and whether you approve of it or not, the film embodies the zeitgeist of now.

The repercussions of the match are just as effectual, as in the heartrending talk between Jessica and her mom that reminds us that moms aren’t as oblivious to our lives and emotions as we’d care to think, and are capable of understanding things about ourselves that we don’t understand yet. Tovah Feldshuh could have easily slipped full force into the “overbearing Jewish mother” stereotype as Jessica’s mom, but she’s a veteran actor and proves it by ripping you apart with surprising, sensitive subtleties emerging from within her aggressive character.

Likewise, Scott Cohen, with his dark, New York good looks, tackles the difficult and complex Josh, who begins as an asshole lashing out in all directions because of his own stifled creativity, then takes a severe turnaround into a born-again novelist. Every step of his long, emotional, self-analytic journey that extends from Jessica’s influence is authentic and honest.

If you’re a single woman, Kissing Jessica Stein is medicine for your tortured Dutch-treat soul. If you’re anything else, it’s simply an original take on an unconventional/soon-to-be-conventional slice of life.

Anita Schmaltz writes about the arts for Metro Times. Send comments to [email protected].

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