A Lot Like Love (2005)

Emily Friehl and Oliver Martin';s first encounter is on a flight from Los Angeles to New York City, during which they join the mile high club. They 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? Each time they meet, one appears to be settled and content while the other is struggling to make headway in both life and career. Eventually they come to the realization that each is exactly the person the other one needs for fulfillment.