Kissing Jessica Stein 2002

Directed by Charles Herman-Wurmfeld | Starring: Jennifer Westfeldt, Jon Hamm, Scott Cohen, Brian Stepanek

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.