The last five years is a musical chronicling a love affair and marriage taking place over a five year period. Jamie Wallerstein (Jordan) is a young, talented up and coming novelist who falls in love with Cathy Hiatt (Kendrick), a struggling actress. Their story is told almost entirely through song. All of Cathy's songs begin at the end of their marriage and move backwards in time to the beginning of their love affair, while Jamie's songs start at the beginning of their affair and move forward to the end of their marriage. They meet in the center when Jamie proposes.