Rob Gordon is a thirty-something former DJ who owns an unprofitable used record shop in Chicago. Barry and Dick are not his employees, but he keeps them there as they show up one day at the shop and have never left. They are all music lovers, though in their own ways. Rob is known for his penchant to compile top-five lists. His latest list is one of his top five breakups. It was inspired by his recent girlfriend Laura (a lawyer) who has recently broken up. Partly because he expected Laura to be his last girlfriend, he believed Laura would prove him right. Rob acknowledges there were some incidents during their relationship that could have led to Laura wanting to end the relationship. Laura has been removed from the top five list to his satisfaction. Rob is forced to look at the five relationships he had, going back to middle school, when he was 12. He also needs to understand why the girl or woman left. Charlie Nicholson is number four on this list. It is also up to Rob to accept that Laura moved on from Ian Raymond. Both of them had no respect for each other when they were together.