“Kissing Jessica Stein” is pure pleasure. A fresh take on sex and the single girl, this buoyant, well-crafted romantic comedy blends pitch-perfect performances with deliciously smart writing by actor-scribes Jennifer Westfeldt and Heather Juergensen. Previously in development at Gramercy (the filmmakers reacquired rights when it seemed their project might atrophy in turnaround), pic has above-average commercial potential for an indie production and would be a feather in the cap of a distributor with the savvy to adroitly position it for a young femme — and potentially broader “Bridget Jones” — audience.
Title character, played by Westfeldt, is a sort of Jewish Ally McBeal who works in a publishing house alongside her garrulous, pregnant friend, Joan (Jackie Hoffman), and smug ex-b.f., Josh (Scott Cohen). Frustrated at her inability to find love, Jessica embarks on a series of disastrous first dates, effectively presented in an amusing montage. It’s only when she reads a personal ad quoting Rilke that Jessica’s interest is piqued, but there’s only one problem: The ad was placed by a woman.
Though she’s resolutely straight, Jessica decides to meet the ad’s author, a free-spirited art gallery manager named Helen (Juergensen). To her surprise and chagrin, the sheltered Jessica is quite taken with Helen. Finding they have much in common — including their heterosexual track records — Jessica and Helen strike up a warm and quirky courtship. As Jessica finds herself falling for Helen, she’s forced to confront her own insecurities, her friends’ preconceived notions, and the apprehensions of her overprotective mother (Tovah Feldshuh).
It all comes to a head at her brother’s wedding, where she must decide whether she’s strong enough to admit their bond publicly. It’s giving nothing away to say that one member of the duo decides she is not a lesbian, a denouement handled with gentle grace and ample humor.
Credible, sympathetic perfs are key to the film’s appeal. Having spent many months exploring Helen and Jessica’s relationship in their stage play “Lipschtick,” Juergensen and Westfeldt know their characters intimately. Their resulting onscreen dynamic, ably guided by Charles Herman-Wurmfeld’s breezy direction, feels entirely naturalistic.
Supporting turns are also first-rate. Feldshuh gives an achingly poignant and multilayered performance as Judy Stein, a woman who is much more perceptive than she appears. And Hoffman gives a terrifically funny interpretation of Jessica’s meddling but well-meaning friend, staying just the right side of caricature.
Tech aspects are tops, notably the editing by Kristy Jacobs Maslin and Gregory Tillman, which helps propel the movie like a fast-moving train. Only fault, and it’s hardly that, lies in the few instances where the laughs come too close together to be digested fully.