Phoebe experiences flashes of one of her past lives when she and her sisters were cousins in the 1920s. However, in this past life, Phoebe was evil and power mad and a curse was bestowed upon her that could affect future Phoebe's life.

After Paige and Henry leave for their honeymoon, Cupid "Coop" takes Phoebe on a journey through her past romances in an attempt to revive her excitement for love. Meanwhile, a group of magical teens, who are protégés of Leo, come to the manor seeking refuge from demons that have overtaken the Magic School, forcing Piper to take charge. Billie and Christy's parents come to town for a visit, but Christy refuses to see them in order to test Billie.