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.

• 
  Charles Herman-Wurmfeld
• 
  Kate Drennen

• 
  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
• 
  Hillel Friedman
  Rabbi
• 
  Ben Feldman
  Ben Feldman
• 
  Ben Weber
  Larry
• 
  Brian Stepanek
  Peter
• 
  Jennifer Carta
  Rachel - Dan's Fiancée
• 
  Idina Menzel
  Bridesmaid
• 
  Vinny Vella
  Cab Driver
• 
  John Cariani
  Chuck
• 
  Kevin Sussman
  Calculator Guy
• 
  Jim J. Bullock
  Not-Yet-Out Gay Guy