In this mid-2000s romantic comedy, two strangers named Oliver (Ashton Kutcher) and Emily (Amanda Peet) meet on a flight from Los Angeles to New York and enjoy the mile-high club together. Upon landing, they decide it'd be best to go their separate ways, but as months go by they can't help but wonder what if. Over the next seven years, fate brings Oliver and Emily together multiple times; however, the timing for a relationship is never right. So, they remain friends — until they're both alone (and thinking about each other) on New Year's Eve.