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