Oliver (Ashton Kutcher) and Emily (Amanda Peet) meet each other unconventionally at the airport. They both happen to notice each other in the crowd and they strike up enough interest to join the Mile High Club. Exiting the airport upon arrival at their destination Oliver tries to establish more of a connection with Emily, when he says he doesn't play the guitar she tells him that is strike two, but won't tell him strike one. The two spend some time together, but part as Oliver gives Emily his phone number and tells her to call him in six years. The story moves forward a few years and they have both changed, Oliver is soon on his way to an internet start-up and Emily is an aspiring actress. One thing is not different, they are both still interested in each other, but Oliver is leaving. Once again they have an interesting night together, and once again they part ways for a few years. After repeating this cycle a couple of more times Emily finds herself at Oliver's house, but he is getting married, or is? Their relationship is about finally being in the right place at the right time, and the question is whether or not they will find each other in that place at that time?