Kissing Jessica Stein (2001) is a romantic comedy about two women who, for different reasons, decide to try dating women instead of men. Jessica Stein (played by Jennifer Westfeldt) is 28 and a nervous perfectionist, and she is feeling desperate about finding “the One.” Helen Cooper (Heather Juergensen) is a free spirit who decides to place a personals ad, and throws in a Rilke quotation on the advice of a gay male friend. Jessica sees the quotation, and despite her unease at the idea of dating a woman, decides this is a possible soulmate. On this shaky beginning builds a relationship — and a film — that investigates the risk/reward ratios of love and life.
Tovah Feldshuh gives a standout performance as Jessica’s mother, a role which initially embodies the “Jewish mother” stereotype but gradually reveals a heart and soul that may make viewers wish for a mother like her. Many of the characters in the film develop along similar lines: we think we know them, and then we get to know them a little better. In the case of the Jessica’s generation, they get to know themselves better. It’s a fine screenplay, and in an interesting turn of art and life, it was written by the two women who play the leads, Westfeldt and Juergenson.
Kissing Jessica Stein won awards from major film festivals and was well-received by critics.
So, you are wondering, why is this film on the “Jewish Film” list at all? Jessica is a Jew. Her family is a Jewish family, and the picture we get of them is much more real and warm than the caricature we usually see in American films. We see this Jewish family in many of the places where families gather: at High Holy Day services, at Shabbat dinner, at a family wedding.
The depiction of her mother is strikingly different from the stock character that is usually trotted out by filmmakers and comics: one cannot help but notice that this film was written by women, not by men. She is anxious for her daughter to marry, and is constantly setting up ambushes with men she thinks are eligible, but she is a wise woman who genuinely loves her daughter, and who knows a thing or two about love.
Jessica Stein is a Jew and Helen Cooper is not. Once Jessica’s family becomes aware of Helen, they try very hard to be welcoming of this lesbian (!) non-Jew (!) and they make most of the usual missteps, on both counts. Their goodwill is obvious, though, and the small scenes in which Helen tries to fit in and they try to make a place for her would make an interesting jumping-off spot for discussion. While the interfaith angle is not a major focus of the film, everything in the film about it is quite good.
That said, Kissing Jessica Stein avoids a serious discussion that it could have had (but then, it wouldn’t be a comedy.) Helen is looking more for interesting sex than for love. Jessica is looking for someone “perfect,” and the subject of love doesn’t seem to have occurred to her. Neither woman is really looking for love, and when they stumble into it, they… stumble. What truly went wrong here, and was it really only the most obvious thing?