Kissing Jessica Stein

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

  Jessica Stein
• 
  Heather Juergensen

  Helen Cooper
• 
  Scott Cohen

  Josh Myers
• 
  Jackie Hoffman

  Joan
• 
  Tovah Feldshuh

  Judy Stein
• 
  Michael Mastro

  Martin
• 
  Carson Elrod

  Sebastian
• 
  Jon Hamm

  Charles
• 
  David Aaron Baker

  Dan Stein
• 
  Esther Wurmfeld

  Grandma Esther