Rob Gordon is a music-obsessed owner of a struggling record store in Chicago. His life is defined by a series of failed relationships, which he examines obsessively. He attributes much of his life's disappointments to his vast knowledge of music, believing that his dedication to the record store and his extensive vinyl collection has been a means to avoid real commitments. When his long-term girlfriend, Laura, leaves him for another man, Rob is compelled to reflect on his past relationships.

In a bid to understand where his relationships went wrong, Rob revisits his "Top 5" breakups. With each interaction, he confronts his own shortcomings and misgivings about love, ultimately questioning his attitudes and behaviors. His journey through his romantic history is paralleled by his interactions with the eccentric employees at his store, who share his passion for music but have their own unique perspectives on life and love.