A demon named Drasi steals Cupid's ring, which he uses to bring couples together, to tear them apart. Now Cupid must convince the Halliwells to help him get it back before Drasi breaks all of the relationships, thus killing Cupid.
The sisters must find a way to vanquish a ghost who is intent on killing all of the men in a family line, including the last male, a baby named Matthew.
Prue cannot resist the attraction she feels for her kidnapper (Antonio Sabato Jr.) when she is abducted by a former flame who is fleeing a powerful demon.
After Prue prevents a woman named Maggie Murphy (Amy Adams) from committing suicide, a Darklighter (Arnold Vosloo) puts a curse on her that throws her into a depression that could cost her life.
An old family friend (Anne Haney) appeals to Piper, Phoebe and Prue to stop a demon (Cameron Bancroft) who peels the skin from corpses; Piper doesn't want to be a witch anymore.
Phoebe helps the ghost of a student who was killed to prevent the publication of her thesis on evil; the Goo Goo Dolls perform at Piper's nightclub. Phoebe helps the ghost of Charlene, a student killed by Libris.
Prue and Phoebe are wondering if Piper will ever return from "up there" with Leo, whilst the sisters are involved in a court case that is crawling with demons.
The sisters must find a way to break a curse which turns a man into an Owl by day and his girlfriend into a Wolf by night. Meanwhile, Prue discovers a way to hold Piper and Leo's wedding without The Powers That Be finding out.
While Piper worries that Leo will never return, Prue and Phoebe try to save a little girl named Kate and a Fairy Princess named Thistle from evil trolls who lurk in the "tweens" and want to capture the princess.
The sisters are sent back in time on Halloween to save a baby from being born into the clutches of evil. Meanwhile, Leo and Darryl are left to keep the grimlocks at bay until the sisters return.
After the manor is burglarized, Prue, Phoebe, and Piper become obsessed with learning more about the elusive evil force that is hunting them. Prue assumes it is demonic, but Darryl cautions them that there is human evil as well.
Phoebe and Piper are on a mission to save Prue after a spell for an innocent horribly backfires and Prue is given the unwanted gift of feeling all the pain in the world. The cacophony of human emotion will most certainly crush her.
Cole uses petty anger between Prue, Phoebe, and Piper to break their bond and destroy the very foundation of their powers, leaving the sisters defenseless against demonic attack.
After Prue, Phoebe, and Piper learn that Cole is the demon that has been trying to kill them, Phoebe faces the tough decision of killing the man she loves or defying her sisters by letting him go free.