Adam Scott
Jason
Jennifer Westfeldt
Julie Keller
Jon Hamm
Ben
Maya Rudolph
Leslie
Chris O'Dowd
Alex
Kristen Wiig
Missy
Megan Fox
Mary Jane
Lee Bryant
Elaine Keller
Kelly Bishop
Marcy Fryman
Cotter Smith
Phil Fryman
Nina Lafarga
Penelope
Vince Nappo
Businessman / Julie's Date
Derek Cecil
Pete
Katie Foster
Girl in Office / Jule's Assistant
Rekha Luther
Life Coach / Jason's Date
John Lutz
Jason's Colleague at Work
Ken Barnett
Stage Manager in Chicago
Edward Burns
Kurt
Ilana Levine
Mom in Restaurant
Brian d'Arcy James
Husband in Restaurant
Steven Weisz
Doorman George
Peter K. Hirsch
Doctor in Delivery Room
James McMillan
Missy's New Boyfriend
Michael Dean
Soho House Waiter (uncredited)
