Heartbreak City/Plot

Max catches up with Cindy, and Cupid makes his move. His ring glows red, and time slows. He encourages Cindy and Max to open up to each other; Max has an ex-wife, and Cindy is suspicious of her, but Cupid tells him to reassure Cindy. Shortly after, Drazi, the demon of hate, attacks Cupid, and steals his ring.

The sisters, Dan and Jack leave the movie "Love Story". It was supposed to be a triple date, but Phoebe is a fifth wheel; her date Kevin canceled. The sisters tell Dan and Jack there are severe penalties for canceling on a Halliwell at the last minute. The two couples go for coffee, but a disappointed Phoebe gets a cab. As she leaves, Cupid seeks Phoebe's help. Dan and Jack chase Cupid away.

Come morning, Phoebe is on the phone with Prue (who is still at Jack's place) when Cupid surprises her. She high-kicks him and hangs up. Cupid tells her who he is.

Dan gives Piper breakfast in bed, and a necklace with a heart-shaped charm. Phoebe and Cupid show up and Piper freezes Dan. Phoebe now believes Cupid and explains the situation to Piper. Phoebe and Cupid leave so Piper can safely unfreeze Dan. Piper gives Dan some quick kisses and leaves, leaving Dan confused.

Drazi spots Max and Cindy and the ring glows green, in contrast to the red seen when Cupid used it.

Prue and Piper still don't quite believe Cupid, pointing out he doesn't look the way they expected. Cupid retorts that the sisters don't exactly look the way witches are supposed to look either. He rattles off a number of the sisters' former beaus, all of which were set up by other Cupids. He claims to have connected Piper to Dan and Prue to Jack, but denies involvement in connecting Piper to Leo, as this is forbidden. His own assignment is only two years old, though. He thinks Phoebe has had trouble finding dates because her heart is closed. They have more important problems though because Drazi is out to destroy love itself. They can sense each other; there is a fine line between love and hate.

Max buys Cindy some flowers, sorry that no roses were available. Drazi appears and uses the ring to slow time. He tells Cindy that Max is still sleeping with his ex-wife, and tells Max that Cindy is only after his money. The two fight, Cindy throws the flowers down, and Max storms off -- right into traffic, where a Corvette hits him. Cupid feels a sharp pain in his heart.

The sisters and Cupid come to the scene of Max's accident, Cupid guiding them by sensing Drazi. Cupid points out Drazi and the four pursue. Drazi is too far ahead, so Prue astral projects. Finding that her telekinesis doesn't work in astral form, she cracks Drazi with a board. Piper, Phoebe and Cupid catch up with Drazi, and Piper freezes Drazi. Phoebe throws a potion, and Drazi melts into a pool of black tar-like substance. Cupid's ring is nowhere to be found. Cupid thinks he can "get back" (where is unspecified) with the Charmed Ones' help, and get a new ring. As the witches and Cupid leave, a green glow appears in the pool of tar, and Drazi re-forms.

Cupid and Phoebe mix a potion to return him home. Cupid explains that Drazi fell in love with a mortal woman, and he had directed her to a mortal man. She is now happily married, but Drazi wants revenge. Cupid and Phoebe get a little closer, but when he suggests that she is falling for him, she pulls away.

Phoebe and Cupid come to P3 and find Dan and Jack. They ask after Prue and Piper, who are in the ladies' room. Both Dan and Jack think they recognize Cupid. Drazi follows, and the ring glows green. Phoebe and Cupid prepare to go to a stockroom to send Cupid home while Piper and Prue return to their respective dates. Drazi makes Dan suspicious of Leo, and tells Jack that Prue is using him. He says something unspecified to Piper. Cupid feels a pain in his chest. The two couples quarrel. Prue and Piper are also angry with Phoebe and Cupid. Cupid thinks perhaps patching his couples up might help him fight back.

Cupid and Phoebe go to Cindy. Cindy doesn't want to talk to them, but the two insist. Phoebe talks to Cindy of love lost, and encourages her to go back to Max. Cindy admits that she loves Max. She meets Max at the hospital, bearing flowers (again, they didn't have any roses), and they reconcile. Drazi is after yet another couple, but now feels pain in his heart.

Phoebe and Cupid gather Dan, Piper, Prue and Jack together. Phoebe tells the two couples of the love she sees between them. Dan perceives that Piper is keeping secrets, and is still suspicious. As the couples begin to reconcile, Phoebe sends Dan and Jack after whatever snacks they want. Just after they leave, Drazi enters and attacks Cupid. Piper freezes them. Phoebe puts the ring back on Cupid's finger and throws a potion. This time Drazi is gone for good.

The three sisters leave another movie, The Dirty Dozen, and this time Kevin accompanies Phoebe.