Comedy / Drama / Romance /

Score: 68%( 1327 votes )

Overview: On a flight from Los Angeles to New York, Oliver and Emily make a connection, only to decide that they are poorly suited to be together. Over the next seven years, however, they are reunited time and time again, they go from being acquaintances to close friends to ... lovers?

Cast:

Ashton Kutcher
Oliver Martin

Amanda Peet
Emily Friehl

Kathryn Hahn
Michelle

Kal Penn
Jeeter

Ali Larter
Gina

Taryn Manning
Ellen Martin

Aimee Garcia
Nicole

Jeremy Sisto
Ben Miller

Gabriel Mann
Peter

Moon Bloodgood
Bridget

Holmes Osborne
Stephen Martin

Lee Garlington
Stewardess

Sarah Ann Morris
Bartender

Joeanna Sayler
Gallery Owner

Meghan, Duchess of Sussex
Hot Girl

Conrad Bluth
Chris

Sarah Shahi
Starlet

Tyrone Giordano
Graham Martin

James Read
Brent Friehl

Melissa van der Schyff
Carol Martin

Molly Cheek
Christine

Kathrine Herzer
Little Girl

Joe Koons
Best Man (uncredited)