In Charmed, it was a rite of passage to date a demon, and all of the sisters have dated at least one. It was Prue’s (Shannen Doherty), Piper’s (Holly Marie Combs) and Phoebe Halliwell’s (Alyssa Milano), and Paige Matthews’s (Rose McGowan) destiny to protect the world with their magic. Unfortunately, that sometimes got in the way of their everyday lives. It created problems for their jobs. And it also made it harder for them to date and trust people with their secret.


Each of the sisters dated multiple men in the series, and occasionally they ended up being a demon or possessed by a demon. Most of the relationships were short-lived, but it became common for the sisters to date a demon. Here are all the demons the Halliwell sisters dated during the show.

Related: How The Original Charmed Still Had 2 More Seasons After Being Canceled

Prue’s Ex-Boyfriend Tom Was Preparing To Become A Demon

Tom Peters (Prue's ex-boyfriend) on Charmed

In season 3, episode 12, “Wrestling with Demons,” Prue Halliwell ran into her ex-boyfriend from college, Tom Peters (Marco Sanchez), when saving an innocent. She was so surprised she accidentally let him get away. The eldest sister discovered Tom was in a supernatural academy turning humans into demons, and Prue was determined to save him before it was too late. She figured out the key to saving her ex, his mother. The sisters stopped him from killing an innocent and reversed his transformation.

Prue Briefly Dated Brendan The Half-Warlock

Brendan Rowe in Charmed

In season 1, episode 18,” When Bad Warlocks Go Good,” the sisters meet Brendan Rowe (Michael Weatherly) while doing a catering gig for the Quake restaurant. They accidentally take his pen, and Phoebe has a premonition about him, and he becomes their innocent. Prue started to like him pretty quickly. She trusted him with their secret because of “his eyes.” He was a half-warlock whose brothers were trying to turn him evil. They even put a spell on him to make him sacrifice Prue. Prue talked him down, but their relationship didn’t last because his ultimate dream was to become a priest.

Piper Was Engaged To Jeremy (A Warlock)

Jeremy on Charmed Pilot

In the pilot episode, Piper Halliwell is engaged to a seemingly nice man, Jeremy Burns (Eric Scott Woods). He revealed himself as a warlock in an abandoned building, with her under the impression he was taking her to see the view, but he wanted to take her powers. He had been lying in wait for the sisters’ grandmother to die and for them to be reunited to get their powers. Jeremy ended up being the first thing the sisters vanquished with the power of three. And it also began the tradition of a Halliwell dating a demon.

Related: Charmed: All 9 Times Phoebe Halliwell Died Explained

Phoebe Had 2 Weeks With Ex-Demon Drake

Drake dè Mon (Billy Zane) was the new literature teacher at Magic School. He had made a deal with a sorcerer that would allow him to live as a human for a year, but he had to give up his immortality. By the time he met Phoebe Halliwell, he only had two weeks left. They spent a lot of time together, and she fell in love with him. This was his mission all along to restore Phoebe’s faith in love. It was revealed that Cole sent him because he believed that Phoebe couldn’t fall in love again because of him.

Phoebe’s Epic Romance With Half-Demon Cole

Phoebe laying her head on Cole's shoulder in Charmed

Cole Turner (Julian McMahon) was Phoebe’s epic love and also one of the show’s central love stories. Unfortunately, Cole was also a half-demon, Belthazor. The Triad sent him to kill the Charmed Ones. Instead, he fell in love with Phoebe, and she fell in love with him. He becomes a reformed demon, and then he becomes human for a little bit. While he’s human, Phoebe and Cole get engaged.

Then, the Seer conjured up a plan to make Cole the new Source (Source of all Evil). He becomes the Source without Phoebe knowing, and she gets pregnant with his demonic child. Eventually, the sisters have to vanquish him. This plays a big role in Phoebe finding love for the rest of the series.

Paige’s Boyfriend Shane Was Possessed By The Source

Shane as the Source on Charmed

In season 4, episodes 1 and 2 (“Charmed Again: Part 1″ and “Part 2”), Paige Mathews discovered she has sisters and is a witch. She was also dating a new guy, Shane (Jordan Bridges). The source possessed him to get close to the sisters. Paige spent time with him while he was possessed. He tried to pull her away from Piper and Phoebe. Shane ended up being okay, but he didn’t understand what happened to him but knew it had something to do with Paige. At the end of episode 1, Piper says to Paige: “You’re not truly one of us until you’ve dated a demon. So welcome to the club.”

More: The 1 Charmed Spinoff Show We Really Wish Had Happened

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