A Lot Like Love (2005)

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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?

Starring: Ashton Kutcher, Amanda Peet, Kathryn Hahn, Kal Penn