Jessica Stein (Jennifer Westfeldt) is a young conservative Jewish girl with the perfect loft situated on New York City's Upper West Side, a fun job working for a hip newspaper, and beautiful clothes. The only thing she doesn't have is the ideal boyfriend. When her coworker, Joan (Jackie Hoffman), reads her an ad from the personals of the Village Voice, Jessica knows she's interested. Even when she realises that the ad is in the 'women seeking women' section, she figures it's worth a try. A funny, girly, prissy, very lipstick-lesbian relationship ensues with Chelsea gallery owner Helen (Heather Juergensen). When the girls aren't making out, they share makeup secrets and raid each other's closets. However, Helen's daring nymphomaniac side clashes with Jessica's conservative straight side, and the couple is forced to face some real challenges.
 

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Offers a swag of witticisms and a delicious sense of romance in which the characters are flawed...

Single 28 year old Jessica, Jennifer Westfeldt gets an attack of the panics when her brother announces his marriage and a colleague at the New York magazine where she works as a copy editor falls pregnant. After a series of unsuccessful dates Jessica responds to a personal ad in the women-seeking-women column that`s been placed by art gallery director Helen, Heather Jurgensen. Helen has three men on the run but wants to explore a relationship with a woman. Tentatively and funnily a romance develops between the two with Helen the more confident and demanding and Jessica the more neurotic.

Directed by Charles Herman-Wurmfeld from a screenplay developed by the two actors, from their off-off Broadway production, Kissing Jessica Stein has a swag of witticisms and a delicious sense of romance in which the characters are flawed, they`re real. It`s smart and funny with very appealing performances by both the leads and with wonderful contributions from Tovah Feldshuh as Jessica`s mother and Jackie Hoffman as her friend Joan. At first it may seem too insistently New York Jewish but when it escapes clich? it`s really terrific. It`s treading in Woody Allen territory but now I think David may ask me to wash my mouth out.....