Jessica Stein is a successful career woman, a writer for a publishing house, intent on finding a lasting relationship. She is also a deeply neurotic but loveable soul--an updated version of Woody Allen's character Annie Hall. One day, as her insistent best friend reads her the ads in the classifieds, Jessica is struck by one which features a favorite quote from Rainer Maria Rilke. Trouble is, the ad is in the "Women seeking Women" section, and Jessica is straight.
After a series of disastrous dates with men, hilariously catalogued with elliptical precision, Jessica decides to answer the ad. The woman behind the ad, Helen, is a novice herself but is much more savvy about modern-day realities. Thanks to Jessica, however, their first date, and in fact much their nascent relationship, becomes a tour-de-force of insecurities, fears and neuroses. Just as Helen is about to give up on her, Jessica relaxes into the relationship--but not enough to tell her mother.
In the end, "Kissing Jessica Stein" is a bittersweet portrait of two lonely individuals who help each other discover the truth about themselves. The scriptwriters confront the delicate nature of this story of two women who decide to experiment, and tackle these issues with characteristic wit and intelligence. And while both women choose different paths, their journey together unravels many cogent insights into contemporary relationships and the sometimes fluid nature of sexuality. Starring and written by Jennifer Westfeldt and Heather Juergensen. Directed by Charles Herman-Wurmfeld. Produced by Eden Wurmfeld and Brad Zions. A Fox Searchlight release. Comedy. Rated R for sexual content and language. Running time: 94 min.