Ashton Kutcher as Oliver Martin

Amanda Peet as Emily Friehl

Kathryn Hahn as Michelle

Kal Penn as Jeeter

Ali Larter as Gina

Taryn Manning as Ellen Martin

Aimee Garcia as Nicole

Jeremy Sisto as Ben Miller

Gabriel Mann as Peter

Moon Bloodgood as Bridget

Holmes Osborne as Stephen Martin

Lee Garlington as Stewardess

Sarah Ann Morris as Bartender

Joeanna Sayler as Gallery Owner

Meghan, Duchess of Sussex as Hot Girl

Conrad Bluth as Chris

Sarah Shahi as Starlet

Tyrone Giordano as Graham Martin

James Read as Brent Friehl

Melissa van der Schyff as Carol Martin

Molly Cheek as Christine

Kathrine Herzer as Little Girl

Joe Koons as Best Man (uncredited)