Kissing Jessica Stein (2002)

1h 37m · Directed by Charles Herman-Wurmfeld

Starring Jennifer Westfeldt, Heather Juergensen, Scott Cohen, Jackie Hoffman, Tovah Feldshuh

Jessica, a Jewish copy editor living and working in New York City, is plagued by failed blind dates with men, and decides to answer a newspaper's personal advertisement. The advertisement has been placed by 'lesbian-curious' Helen Cooper, a thirtysomething art gallerist.