Constructed as a series of chapters that take place at a turning point in each character's life, the story moves from seven years in the past to three years to two and finally arrives in the present day. Emily Friehl (Amanda Peet) and Oliver Martin's (Ashton Kutcher) first encounter is on a flight from Los Angeles to New York City. He has hopes of becoming an Internet entrepreneur and, certain of his future success, gives her his mother's phone number and suggests she call him in six years to see if his prediction came true.