With her biological clock ticking away and a sarcastic boss (Scott Cohen) who's also her ex-boyfriend, Jessica begins to believe what everyone has been telling her: She's too picky. Terminally insecure, Jessica hits upon a rather bold realization perhaps she's playing for the wrong team. Instead of looking for a nice Jewish boy, what if her true happiness is waiting for her within her own gender pool?
Intrigued by a "woman-seeking-woman" ad in the personals, Jessica decides it's time to see how the other half loves. With some reluctance, she agrees to meet Helen (Heather Juergensen), a hip gallery manager who's decided to experiment with same-sex relationships after finding a multitude of affairs with men deeply unsatisfying. Helen is the more eager; she finds the skittish Jessica frustrating and calls her the "Jewish Sandra Dee."
Like any other romance worth its salt, "Kissing Jessica Stein" makes comedic hay with Jessica's and Helen's lack of experience and copious anxieties. And although Jessica eventually succumbs to Helen's considerable charms and their shared taste in footwear, there are still huge issues between them: Will newly minted lipstick lesbian Jessica find a way to discuss her romance with her therapist? Will she come out to her family or friends? And most importantly, is this lifestyle/love a permanent choice for both women or merely a phase?
There are plenty of laughs throughout "Kissing Jessica Stein," and to first-time big-screen director Charles Herman-Wurmfeld's credit, the movie doesn't entirely gloss over the reality of messy sexual politics. Plus there's the magical chemistry between Westfeldt and Juergensen, who've spent years developing these two characters, first in an off-Broadway play and now on screen. The supporting cast is equally impressive and funny, especially Feldshuh as Jessica's concerned mom and Jackie Hoffman as Jessica's yenta-ish, pregnant best friend.
One of the movie's best scenes takes place between these two old friends, when Jessica finally confesses what she's been up to and her best friend admits she's jealous.
Forget the gender labels. "Kissing Jessica Stein" revels in its lack of depth as well as its alternative lifestyle pretensions. The result is an extremely funny, good-spirited romantic romp with a sweetly uncomplicated message about love and friendship. S