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Kissing Jessica Stein (2001) - Overview, Synopsis, Critique

helen relationship film jennifer

Principal social theme: homosexuality

Fox Searchlight. R rating. Featuring: Jennifer Westfeldt, Heather Juergensen, Scott Cohen, Esther Wurmfeld, Hillel Friedman, Robert Ari, David Aaron Baker, Jennifer Carta, Ben Webber, Brian Stepanek, Nick Corley, Jackie Hoffman, John Cariani, Michael Mastro, Michael Showalter, Jon Hamm, Tovah Feldshuh; Written by Jennifer Westfeldt and Heather Juergensen. Cinematography by Lawrence Sher. Edited by Kristy Jacobs Maslin and Greg Tillman. Produced by Eden H. Wurmfeld and Brad Zions. Directed by Charles Hermann-Wurmfeld. Color. 96 minutes.


Kissing Jessica Stein was an engaging attempt to portray lesbianism in a fresh fashion. The result is a light romance reminiscent of the popular romantic comedies from the 1950s and 1960s, but peppered with a dash of hip Woody Allen humor. The story depicts the romance of a bisexual art gallery manager and a straight but high-strung journalist weary of dating unsuitable nerdy men. Beneath the froth, the film provides an honest and serious consideration of human sexuality. Kissing Jessica Stein won numerous awards as best picture at independent film festivals.


Jessica Stein (Jennifer Westfeldt) is an intense journalist in her late twenties who is becoming increasingly frustrated in her love life. Her mother, Judy (Tovah Feldshuh), and her grandmother, Esther, continually try to set her up with new suitors, hoping to find Mr. Right. They even size up possible candidates while attending services at the synagogue. She has a series of dates, finding each of them unsatisfying. Josh (Scott Cohen), Jessica’s boss, is her old college flame, and he makes a cruel observation that Jessica is far too fussy and will never find a man who will meet her standards. Helen Cooper (Heather Juergensen) is a sexually active woman who manages an art galley. In spite of her many boyfriends, she finds herself more attracted to women. With the help of Sebastian and Martin, two homosexual friends with whom she runs the gallery, Helen writes a heartfelt personal column ad in the paper seeking a new relationship. Jessica is moved by the ad, even though it appears in the section of “Women Seeking Women.” Feeling depressed after learning that her brother, Dan, had become engaged, Jessica calls Helen and they agree to meet. Jessica is very nervous and uncertain about this move, and after meeting Helen in a coffee shop, tries to back out. Helen deliberately dumps the contents of her purse in the street, and Jessica stops to help her as they begin to chat. Eventually, they wind up at a restaurant and talk all night.

Walking home, Jessica states that she could not consider a lesbian relationship. In response, Helen kisses her and walks away. Jessica is both stunned and intrigued, finally deciding to contact Helen again, telling her she is willing to give the relationship a try, but she wants to keep their liaison a secret. Jessica insists on taking things slow, but Helen wants to seduce her as quickly as possible. When she finally sparks a response from Jessica, one of Helen’s boyfriends shows up at her apartment, and Jessica makes an excuse to leave. Finally, Judy Stein invites Helen to the Stein home for Shabbat dinner and to meet Jessica’s brother Dan. When the weather turns bad, she is invited to stay over, sharing Jessica’s bed at last. Helen becomes hurt, however, when she learns that Jessica was not planning to bring her to Dan’s wedding. Being very perceptive, Judy figures out the situation and tells her daughter that Helen is a very fine person. Jessica invites Helen as her guest to Dan’s wedding, bringing their relationship out into the open. She decides to move in with her. Jessica also decides to quit her job and become an artist. Months pass, and Jessica is completely happy with the relationship, but Helen is frustrated because she feels that Jessica never wants to make love. Helen finally decides to dump her. More months pass, and Josh runs into Jessica in a bookstore. When he learns that she is no longer with Helen, he asks her out. Later, Jessica meets Helen at a cafe. They have become best friends now that they are no longer lovers, and Helen advises Jessica in her renewed romance with Josh. So at the conclusion, Jessica has returned to the straight world and Helen has chosen to continue wholeheartedly as a lesbian.


Written and occasionally improvised by its two co-stars, Kissing Jessica Stein owes its success to the believability of the main characters and their changing attitudes. Although influenced by such television series as Friends and Sex and the City, Kissing Jessica Stein has its own unique vitality. Jessica is a “type A” personality in the extreme—hypercritical yet totally lacking in self-confidence. She chatters on and on, covering her insecurity as best she can. She became so frustrated with her love life that she wanted to try something different, as long as it was genuine. Once she entered the relationship with Helen, she remained tentative until she received her mother’s approval. At that point, she reached her own comfort level, relaxed, and became herself. Unfortunately for Helen, Jessica was not a lesbian at heart. She just basked in the glow of the “sisterhood” of her relationship with Helen, which lacked any true passion. Helen, on the other hand, wanted to be desired more than anything. This was perhaps the reason she had so many boyfriends. She wanted to find that same intensity level with a woman, something Jessica could never provide. It is fascinating to listen to Helen’s uninhibited conversations with her two gay artist friends. At one point she refers to Jessica as “a Jewish Sandra Dee,” reinforcing the 1960s film undercurrent.

Jennifer Westfeldt is a wonderful actress who really brings Jessica alive. Her voice has the same mellifluous tones as Helen Hunt, but often accelerated to a crescendo that is simply amazing. Jessica becomes more appealing as the film wears on, losing the high tension level that is so abrasive in the opening scenes. Heather Juergensen is far more sensual as Helen, more down to earth and honest. She is the more interesting of the two main characters. Kissing Jessica Stein can provoke lively discussion about the nature of friendship, romance, and the actual nature of lesbianism. It is also an extremely amusing film, shot almost entirely on location in New York City. One interesting point, much of the footage was reedited before the film’s release to cut out the many visual references to the World Trade Center contained in the original print.

Kitasato, Shibasaburo [next] [back] KISS Meets the Phantom of the Park

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