Kissing Jessica Stein (2001)


(director: Charles Herman-Wurmfeld; screenwriters: from a play “Lipschtick” by Heather Juergensen & Jennifer Westfeldt; cinematographer: Lawrence Sher; editors: Kristy Jacobs Maslin/Greg Tillman; music: Marcelo Zavros; cast: Jennifer Westfeldt (Jessica Stein), Tovah Feldshuh (Mrs. Judy Stein), Scott Cohen (Josh Myers), Heather Juergensen (Helen Cooper), Jackie Hoffman (Joan), Esther Wurmfeld (Grandma Esther), Michael Mastro (Helen’s Gay Friend), Carson Elrod (Helen’s Gay Friend), David Aaron Baker (Dan Stein), Michael Ealy (Greg), Robert Ari (Sidney Stein); Runtime: 94; Fox Searchlight release; 2001)

“The picture works best when it isn’t so concerned about its hot button lesbian sexual subject matter.”

Reviewed by Dennis Schwartz

Kissing Jessica Stein is an indie film made for a paltry $980,000. It’s a lesbian comedy/romance, bittersweet sitcom movie, that works as both a comedy and as a serious tale. It’s based on the brief six-night running off-Broadway play “Lipschtick” by Heather Juergensen & Jennifer Westfeldt, who also star in the film. The good chemistry between the star performers and the easy-going wit and fluidity of the story, allow this situational comedy room to develop into a credible film about relationships. It is not an original film but mindful of many other New York City based films about the Jewish subculture, not the least being Woody Allen’s “Annie Hall.”

Jessica Stein (Westfeldt) is a snob, a perfectionist and a graduate of Brown University who is working as a copy editor for The Village Voice, while also aspiring to be a painter. She’s a sensitive but neurotic woman in her late twenties who suffers from insomnia and sadness because of being single. Her snarky boss is her ex-boyfriend from college Josh Myers (Cohen), whom she has a dueling verbal relationship with. Her well-adjusted lawyer brother Danny has just announced his wedding date, which makes her envious that he found happiness. She’s disheartened about all the losers she’s going out with as the single scene is viewed as hell, as one date wants to split the check with her, another is a pompous bore, and one has problems with basic grammar. Her overbearing suburban Scarsdale Jewish mother Judy Stein (Feldshuh) keeps trying to fix her up with a Jewish Prince, but she’s unimpressed with her mother’s choices.

Jessica’s close friend at work is Joan Levine (Hoffman), who also puts subtle pressure on her to get a mate. The pregnant Joan reads in a mocking way a personals ad placed in The Voice by a female looking to meet another female. The ad quotes from the poet Rilke, who happens to be a favorite of Jessica’s. On a whim, even though she has never had a lesbian experience, she answers the ad and meets the sender, a sexually liberated bisexual Chelsea art gallery director and gentile, Helen Cooper (Juergensen). The Rilke quote was given to her by her two homosexual friends to make the ad classy, as she is not familiar with the poet and with the art of placing such ads.

Helen is discontented with her juggling around of three insensitive male lovers, one of whom we see is a black messenger (Ealy) who practically rips off her clothes having a quickie without any feelings. This she says satisfies her horny side.

Jessica is very tentative and uptight about the gay relationship, as the experienced Helen has to go slow with her and ease all her tensions about having gay sex. Their relationship blurs the line between friendship and romantic love, but ultimately finds an eloquent way for them to experience both.

The picture works best when it isn’t so concerned about its hot button lesbian sexual subject matter and is able to get the cute Jessica to stop being so cute and to open up more dimensions to herself. Jessica begins to blossom when stung again by a failed relationship and begins to know more about herself because she is taking risks in her personal life as well as in her career.


REVIEWED ON 5/10/2002 GRADE: B –