1h 47m
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There's nothing better than a great romance... to ruin a perfectly good friendship.
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?
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