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A Ranking of Phoebe Halliwell's Relationships on "Charmed"

Rachel M. Johnson is a lover of all things pop culture. She's been writing about music and entertainment online for years.


Phoebe Halliwell's Boyfriends

Phoebe Halliwell (Alyssa Milano) may be a strong and resilient witch on the hit WB show Charmed, but she was truly unlucky in the love department. From mortals to demons, movie characters to cupids, the character has truly had her fair share of love interests. Let's take a closer look at her most notable romances.

9. Miles

Phoebe was in a relationship with Miles (Ken Marino) following her divorce in Season 5, and continuously started having premonitions of his death. Due to him being destined to die, every time she rescued him Phoebe herself was killed. Phoebe seemed to genuinely care for Miles and desperately tried to save him, but it was later revealed that by doing so she caused a time ripple. In the end, she had to allow his death to happen and the character was never mentioned again.

8. Clay Muniz

Clay Muniz (Victor Browne) was Phoebe's first love interest on the show and ex-boyfriend, who returned to San Francisco in hopes of convincing Prue to sell an Egyptian urn he found. His appearance instantly brought back sparks between him and Phoebe, and their relationship once again turned romantic. After the Guardian of the Urn attacked Clay, he was redeemed by saving Phoebe and acting selflessly. Though the two ultimately did not continue their relationship, they parted on good terms.

7. Leslie St. Claire

Leslie St. Claire (Nick Lachey) became Phoebe's ghostwriter for her Ask Phoebe column when she decided to take a sabbatical. There is an instant attraction between the two when Phoebe finds out Leslie is actually a man. Initially, she is skeptical that a man could properly write her column, but eventually accepts his abilities and the two develop a connection. Their chemistry soon fizzled out, due to him feeling that Phoebe was hiding something and was constantly unavailable for dates. When she was unable to explain why she was doing witch-related activities, Leslie ended things and left town.

6. Dex Lawson

Dex Lawson (Jason Lewis) was introduced in Season 8, when the Halliwell sisters faked their deaths and held a memorial service. Dex was a local artist who had been interested in Phoebe before her death but never acted on it. Living with a new identity as Julie Bennett, Phoebe got a premonition of the two getting married and rushed the new relationship. Not realizing the premonition was due to Billie's spell, Phoebe and Dex were married. After only a month of being in disguises, the Charmed Ones decided to reclaim their old identities and Phoebe decided to tell Dex she was a witch. He did not take the news well and asked for the marriage to be annulled, resulting in the pair parting ways.

5. Billy Appleby

Though Billy Appleby (Chris Payne Gilbert) might have been a fictional movie character, the attraction and connection between him and Phoebe was definitely obvious. Billy was Phoebe's first love and the star of her favorite movie, Kill It Before It Dies. He was brought into the real world by the Demon of Illusion, making her childhood dreams come true. Billy protected Phoebe and the Halliwell sisters when movie murderers chased them throughout the manor, and in the process he helped restore her faith in men. Their short-lived romance was innocent and sweet, and it proved to Phoebe that chivalry and good guys still existed in both the fictional and real world.

4. Jason Dean

Jason Dean (Eric Dane) was the new owner of The Bay Mirror, and despite initially seeming like a strict boss, he and Phoebe began dating after connecting online. Their chemistry and romantic feelings for one another initially started out lustful, but soon became genuine and they fell in love. When Jason had to move to Hong Kong, their relationship continued and Phoebe even ended up moving there with him. Jason was a supportive and caring boyfriend, and their relationship was definitely different from her other ones. Phoebe trusted Jason enough to reveal her secret of being a witch, though he ended up struggling with the declaration. The two split up on good terms, with Jason even potentially sacrificing a business merger in order to protect Phoebe.

3. Drake dè Mon

Though short-lived, Phoebe's relationship with former demon Drake dè Mon (Billy Zane) was arguably one of her most important. Their romance was passionate and exciting from the start, and Drake ultimately helped to restore Phoebe's faith in love. Their two week relationship was doomed, however, due to Drake making a deal with a sorcerer and being destined to die. It was fun watching them go on adventures together, especially when they astral projected to the Cabaret Fantome. Drake helped open Phoebe's heart up to love again, and he spent his last day convincing the distressed Halliwell sisters to never give up on love. It was later revealed that Cole had been the one who sent Drake to Phoebe, fearing that she refused to hold onto love because of what he had done to her.

2. Coop

Who better to fall in love with than Cupid himself? During the final season, the Elders sent a cupid to Phoebe in order to heal her heart once more and repair her faith in love. What soon transpired (to no surprise) was a deep and genuine romance between the pair. Coop (Victor Webster) first developed romantic feelings for Phoebe, but remained focused on putting the Charmed One's happiness and well-being above his own. His kindness and selflessness caused Phoebe to fall for him too, and the couple ended up getting married. Interestingly, Phoebe learned that the first letter of her true love's name was a C in the Season 3 episode "All Halliwell's Eve," resulting in the prophecy being double fulfilled with Cole and Coop. The latter becomes the man of Phoebe's dreams and she finally is granted her much deserved happy ending.

1. Cole Turner

Even though Phoebe ended up in a wonderful and healthy relationship with cupid Coop, many could argue that the love of her life was none other than Cole Turner (Julian McMahon). The two had a whirlwind romance that was full of both passion and plenty of heartache, and there's no denying the pair had chemistry with a capital "C." Cole was first introduced as a half-demon in Season 3, and despite a roller coaster romance the lovebirds emerged stronger than ever. It all went downhill when Cole became the Source, leading to one giant "oh-no" after another. Their passion for one another eventually ended, resulting with Phoebe helping her sisters vanquish her husband. Thankfully, our favorite demon managed to redeem himself by sending Drake to Phoebe and ultimately becoming at peace with himself and his fate.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2019 Rachel M Johnson


Rachel M Johnson (author) on November 22, 2019:

Hi Charles, I actually have heard talks that the original cast is trying to bring the original Charmed back on Netflix!

Charles miller on November 22, 2019:

I wish they would bring the first ones to come on the reboot charmed

Rachel M Johnson (author) on November 02, 2019:

Hi Jacqueline, I completely agree! Cole was so handsome and him and Phoebe had off the charts chemistry! But I totally know what you mean about him and Prue. I definitely think there was a little something there!

Jacqueline G Rozell on November 02, 2019:

Cole was the hottest, the sexiest, the best. And the scenes with Pru when he and the eldest Charmed sister went back in time to the Wild Wild West, the sparks and chemistry between them were so intense I fully expected a season of "almost but not quite" love affair with them. They were sizzling.