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.
Jennifer Westfeldt
as Jessica Stein
Heather Juergensen
as Helen Cooper
Scott Cohen
as Josh Myers
Jackie Hoffman
as Joan
Tovah Feldshuh
as Judy Stein
Michael Mastro
as Martin
Carson Elrod
as Sebastian
Jon Hamm
as Charles
David Aaron Baker
as Dan Stein
Esther Wurmfeld
as Grandma Esther