If the traditional way in which relationships emerge is that parents select partners who marry, have children, and stay together is the uncomplicated paradigm, what is the paradigm for success in complex twenty-first century America, where relationships are formed by individual entrepreneurs who do not have to fit into stereotypic roles? In Kissing Jessica Stein, directed by Charles Herman-Wurmfeld, entrepreneurial chessgames emerge in which the players have to make up the rules as they go along, but they can end up checkmating themselves and starting the game all over again, sacrificing their relationships to find their identities. The film is based on Lipstick, a New York stageplay that lasted six days but caught the attention of Hollywood studio executives. Jennifer Westfeldt and Heather Juergensen, the writers (who are the two principal characters, Jessica Stein and Helen Cooper, respectively) came together to write the story in response to their own false starts in developing male-female relationships. Although straight, they found themselves portraying how two thirtysomething women fell in and out of love. The film begins to delineate the character of journalistic copyeditor Jessica as she is underwhelmed while meeting men in response to a personals ad, presumably under pressure from her mother Judy (played by Tovah Feldshuh), who has invited countless men over to dinner so that she will find an acceptable husband for her hard-to-please daughter. Meanwhile, bisexual Helen works alongside gays in organizing art exhibits for a gallery but has occasional torrid sex with a boytoy, a young African American parcel courier. One day Jessica uncalculatingly answers Helen’s personal ad because she quotes Rilke. When Jessica arrives at a bar to meet Helen, she almost immediately tries to run out, realizing that she is venturing into an unintended Lesbian encounter, but Helen persists, the two get better acquainted, Helen patiently allows Jessica to come out sexually, and the two move in together as lovers. Months later, problems emerge. Jessica’s brother is about to marry, but she has not arranged to invite Helen to the wedding, thus shutting her lover into a closet of her life; but that problem is solved when Helen is invited after all, and the family calmly accepts the two women as lovers, proving that Jessica’s fears of family rejection were unfounded. A more serious problem develops when Jessica stops having sex with Helen, presumably bored, so they split but remain friends who cherish “the way they were.” Interweaved in the story is the pursuit of Jessica by her boss Josh Myers (played by Scott Cohen), who ultimately learns with equanimity that she has been rejecting men for many years because of a Lesbian impulse that was bottled up inside. Professionally, when he stops pursuing Jessica, he overcomes writer’s cramp, while Jessica quits her work at the newspaper to become a freelance artist.. Thus, as self-stereotyping ends, and the various characters find and change roles that give depths of their personalities freer expression, the ending is upbeat. Kissing Jessica Stein may serve to explain what some thirtysomething professional women are now experiencing in the more cosmopolitan corners of America, as well as gay men who experience the same pattern in their lives. But unanswered is the question of just how happy they will be after so many ephemeral encounters by the age of fifty or sixty. That film has yet to be made. MH