Brought together by their shared love of music, ten years on Liam and Natalie are at breaking point. In their case opposites attract but don't necessarily work long-term. Making the difficult decision to separate, they must split their prized music library. But the soundtrack that defined their relationship keeps pulling them back together.
When record store owner and compulsive list-compiler Rob Gordon gets dumped by his long-time girlfriend, Laura, because he hasn't changed since they met, he revisits his top five breakups of all time in order to figure out what went wrong. As he examines his failed attempts at romance and happiness, the process finds him being dragged, kicking and screaming, into adulthood.