Heartbreak City
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.
Tropes
- Accidental Hero: Cindy and Max reconnecting ends up preventing Drazi from preying on another couple elsewhere in the city.
- Allergic to Evil: Cupid gets hurt every time the demon of hate unmakes a relationship he put together.
- Allergic to Love: Cupid theorizes that reconnecting those relationships will hurt Drazi. He's right.
- Alone Among the Couples: Phoebe's date doesn't show up leaving her the awkward tagalong with Piper & Dan and Prue & Jack.
- Armor-Piercing Response: Prue and Piper are skeptical of Cupid's claims, until he starts name-dropping their current relationships and past loves. In particular, a close-up of Prue has her staring in stunned silence after Andy is mentioned, while Phoebe gets flustered over her list of past loves proving to be quite long.
- Big "SHUT UP!": The feuding couples when Phoebe tries to pacify them at the club.
- Breakfast in Bed: Dan gives Piper breakfast in bed, and a necklace with a heart-shaped charm.
- Continuity Nod: To prove he's who he says he is, Cupid references the sisters' past relationships. Besides the more prominent Andy (who he offers condolences for), Dan, and Jack, he mentions Clay. He also insists he had nothing to do with Jeremy the Warlock and that he wasn't allowed to connect Piper and Leo due to the ban on Witch-Whitelighter relationships.
- Foil: During their conversation at the club, we see Dan being like a Secret Chaser curious about Piper's unusual behavior, while Jack is more like a Mellow Fellow aware of Prue's similar behavior but willing to just roll with it.
- Foreshadowing: Phoebe's problems with love will be a recurring problem throughout the series. Cupid also mentions there are multiple agents like himself, which ends up setting up Coop's existence. Phoebe being able to aid Cupid could foreshadow the reveal that love is her true power. It also foreshadows her working on a relationship advice column.
- Freudian Excuse: Phoebe's problems with love and keeping people at a distance stem from having suffered multiple tragedies in her life. In particular, her Parental Abandonment.
- Green-Eyed Monster: Drazi meddles by whispering to Cindy that Max is still seeing his ex-wife behind her back. He also gets in Dan's head by telling him that Piper still loves Leo and that she's only with him out of geographic convenience.
- Hands-On Approach: Cupid uses this method to show Phoebe how to properly stir the potion they're making to send him home.
- Hidden Heart of Gold: Phoebe's not being a jerk about it (well, except when verbally sparring with Cupid), but she insists she's not closed off to love and that she's just too busy to pursue relationships. Cupid surmises that she puts up a tough front because she's afraid of loss.
- I Just Want to Be Normal: As good as the double date was going before Drazi showed up, Piper is a bit glum since their magical lives will always loom over things. Prue acknowledges they'll never really have normal lives but still feels they can try to get as close to that as possible and find a balance.
- Ignored Epiphany: At the manor after the break-ups, Prue starts to wonder if Drazi had something to do with all this, but she's convinced by Piper that's not possible and goes back to badmouthing the guys.
- It's Personal: Drazi fell in love with a mortal woman, but Cupid redirected her towards a mortal man for her own good. Drazi thus blames Cupid for denying him love and is out to get him.
- Lampshade Hanging: Dan talks to Jack about occasions where he's talking to Piper, time suddenly seems to stand still, and then she's acting like a different person. He also questions the seemingly never-ending parade of strange people who show up at the manor and prompt the sisters to leave at a moment's notice.
- Never Recycle Your Schemes: Averted. Phoebe says they'll repeat the same potion to take out Drazi, but this time, Cupid will be wearing the ring.
- Not Quite Dead: Drazi survives the initial encounter because he was still wearing Cupid's ring.
- Not So Similar: Piper thinks their big secret will ultimately derail their relationships. Prue says that everyone has secrets, but Piper remarks it's unlikely Dan and Jack could match theirs.
- "Oh, Crap!" Smile: Phoebe in response to Prue and Piper noticing just how long her list of past loves is.
- Oh, No... Not Again!: Drazi when exposed to the potion for the second and final time.
- On the Rebound: Drazi tells Jack that he's just the rebound guy that Prue is using to have some fun. Prue later admits she actually is on the rebound.
- Passive-Aggressive Kombat: Cupid just keeps needling Phoebe about her closed heart in order to force her to talk about it.
- The Power of Love: It's an episode with Cupid, so this comes up quite a bit.
- Cupid stresses that he and his fellow agents don't make relationships happen; they just help people meet and leave it to them.
- Cupid tries to teach Phoebe the importance of opening her heart to others. He says her past relationships failed because she wouldn't even try and that people eventually give up if they think there's nothing there.
- Cupid notes that setting up connections between witches and Whitelighters are forbidden—meaning Piper and Leo's relationship was entirely their own doing.
- Cupid feels pain when Drazi breaks apart relationships he set up. He reasons that the reverse is true if he and Phoebe can get said couples back together.
- Properly Paranoid: Dan doesn't know about Piper's power, but he can't shake how her attitude and priorities change from one seeming moment to the next.
- Really Gets Around: Cupid's list of past loves is noticeably longer for Phoebe than Prue or Piper. Phoebe says she didn't love all of them, but Cupid says they all wanted to love her and that her closed heart eventually pushed them away.
- Shout-Out: In The Teaser, the couples and Phoebe are seen leaving a theater playing Love Story. In the end, they're leaving after seeing The Dirty Dozen, and Jack and Dan look forward to seeing Death Wish (1974) next time.
- Villain Has a Point: Thanks to the ring, Drazi knows all about his targets. He tells Dan that Piper still loves Leo and that Jack is Prue's rebound guy. Though it's not nearly as vicious as Drazi made it sound to the guys, Piper later admits she does still think about Leo, and Prue says she is on the rebound.
- You Don't Look Like You: Invoked. Prue and Piper initially doubt that Cupid is who he says he is because he doesn't look like typical artist renderings. Cupid says he hears this a lot and jokingly counters here by asking the sisters were their pointy hats are.
- You Keep Telling Yourself That: Prue and Piper insist they're better off without Jack and Dan and that they're not worth crying over.
