Adam Scott as Jason Fryman

Jennifer Westfeldt as Julie Keller

Jon Hamm as Ben

Maya Rudolph as Leslie

Chris O'Dowd as Alex

Kristen Wiig as Missy

Megan Fox as Mary Jane

Lee Bryant as Elaine Keller

Kelly Bishop as Marcy Fryman

Cotter Smith as Phil Fryman

Nina Lafarga as Penelope

Vince Nappo as Businessman / Julie's Date

Derek Cecil as Pete

Katie Foster as Girl in Office / Jule's Assistant

Rekha Luther as Life Coach / Jason's Date

Peter K. Hirsch as Doctor in Delivery Room

John Lutz as Jason's Colleague at Work

Ken Barnett as Stage Manager in Chicago

Edward Burns as Kurt

Ilana Levine as Mom in Restaurant

Brian d'Arcy James as Husband in Restaurant

James McMillan as Missy's New Boyfriend

Michael Dean as Soho House Waiter (uncredited)

Steven Weisz as Doorman George