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
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
