Kissing Jessica Stein

Kissing Jessica Stein is a 2001 independent romantic comedy film, written and co-produced by the film's stars, Jennifer Westfeldt and Heather Juergensen. The film also stars Tovah Feldshuh and is directed by Charles Herman-Wurmfeld. The film is based on a scene from the 1997 off-Broadway play by Westfeldt and Juergensen called Lipschtick.

Plot

Twenty-eight-year-old Jessica Stein (Jennifer Westfeldt), a Jewish copyeditor living and working in New York City, is plagued by failed blind dates with men, and decides to answer a newspaper's personal advertisement containing a quote from Rilke that she had read and admired earlier. The advertisement has been placed by Helen Cooper (Heather Juergensen), a thirtysomething art gallerist bisexual who is seeking a lesbian relationship to replace her unsatisfying and meaningless sex with men.

Given some of the men Jessica is shown to be test-dating at the start of the film, ranging from borderline gay to nerd, some would probably say that it's no surprise she'd want to fan out her prospects a little. As nervous as Jessica is about dating Helen, she realizes after a surprise kiss that even a different experience can be good. Through the early part of their relationship, Jessica finds in Helen everything she'd dreamed of finding in a man. They are compatible, they like many of the same things, and they are caring for one another. Even when Helen gets...
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