In the original Charmed, no one was as unlucky in love as Phoebe Halliwell (Alyssa Milano). Phoebe was the youngest child of Patty Halliwell (Finola Hughes) and Victor Bennett (James Reed), and the middle sister of the Charmed Ones. She also worked as a columnist for "The Bay Mirror," where she provided her readership with relationship advice.
This was only possible due to her own unfortunate love life. While Phoebe believed she had found her Mr. Right, most of these relationships were doomed for disaster. From her relationship with Billy (Chris Payne Gilbert) to her rocky romance with Cole (Julian McMahon), here are 10 of Phoebe's love interests, ranked.
10 Leo Wyatt
There was no doubt that Leo (Brian Krause) and Phoebe were meant to be friends. The chemistry Krause had with Marie-Combs was just too good to ruin, with fans getting behind Piper (Combs) and Leo quickly. But some may not remember that Phoebe was also interested in the handyman in season 1.
It's even weird to think about it now. Imagine if the writers would have paired these two up: what storylines would they have come up with? would the show have ended differently? Fortunately for Piper, Phoebe admitted she was only interested in the Whitelighter because Piper was.
Miles (Ken Marino) began dating Phoebe in season 5 soon after her first divorce. However, his relationship with Phoebe was doomed from the start when she began to receive premonitions about his death ("A Witch In Time").
Phoebe seemed to care for Miles and did everything she could to prevent his death. Yet, it was soon revealed that she caused a time ripple every time she saved him. This allowed the warlock, Barraca, to travel through and kill Phoebe and Paige. Piper had to jump into the time ripple to warn her past self about the consequences of saving Miles. Ultimately, Phoebe was upset when Miles died but never mentioned him again.
8 Clay Muniz
Clay (Victor Browne) was Phoebe's ex-boyfriend and her first love interest. He appeared in the episode "Feats of Clay", returning to San Francisco to try and convince Prue (Shannen Doherty) to sell an Egyptian urn he found. He also briefly reconnected with Phoebe during his stay.
However, their relationship became strained when the sisters discovered he had stolen the cursed urn. He redeemed himself near the end of the episode when he risked his life to protect Phoebe from getting killed. After the Charmed Ones returned the urn, Clay then goes back to New York. He is another character fans don't hear from again.
7 Dex Lawson
Dex (Jason Lewis) was Phoebe's second husband who was introduced to the show in season 8. Dex had expressed an interest in Phoebe but only when she was under the pretense of Julie Bennett. Phoebe was seen to rush into this relationship after she received a premonition that the two were married. They eventually tied the knot under the influence of Billie's spell.
However, it was already implied that this relationship would not last as the Charmed Ones decided to reclaim their old identities. When Phoebe reveals her powers by glamouring back into Julie, Dex doesn't handle the news well. Ultimately, he asks Phoebe if they could have the marriage annulled and the two-part ways.
6 Billy Appleby
Billy was a movie character who had a very brief relationship with Phoebe in season 2. He was the protagonist of Phoebe's favorite film who was able to come to life after the Demon of Illusion brought him into the world.
Billy had always been respectful and protective of Phoebe, particularly in the episode "Chick Flick" when he protected her from the other slasher villains. Sadly for Phoebe, her dream guy had to be returned to his film in order for the world to return to normality. It is implied that she still watches the film on a regular basis as Cole uses it to reveal his return ("Bride and Gloom").
5 Leslie St. Claire
Leslie (Nick Lachey) was a mortal who was hired as a Ghostwriter after Phoebe decided to take a sabbatical. Upon the first impression, Phoebe was skeptical of the writer as she felt he wouldn't be able to give her column the justice it deserved. They also clashed regularly because of their creative differences.
Their relationship took a romantic turn after the two fought about Phoebe standing him up. Yet, this relationship was doomed from the start after Phoebe regularly stood him up on dates and refused to divulge about her other life. Her secrecy was one of the main reasons why they broke up. Still, Phoebe thanked him for helping her get over her fear of love.
4 Jason Dean
Jason (Eric Dane) was introduced to the show back in season 5 after he bought the Bay Mirror. He and Phoebe got off to a rocky start after his strict management conflicted with Phoebe's Wiccan duties. However, they soon began a relationship after Jason managed to charm her with his online profile.
Lasting 15 months, Phoebe's relationship with Jason was different from all the others. He was the first mortal love interest Phoebe trusted enough to reveal her secret to. He also proved to be a very supportive boyfriend, giving Phoebe advice on how to improve her column. Yet the couple wasn't meant to last after Jason struggled to come to terms with her identity as a witch. They did part on good terms.
3 Drake De Mon
Out of all of Phoebe's boyfriends, Drake (Billy Zane) played an important part in restoring her faith in love. Drake was a former demon that was introduced in season 7 as the new literature teacher of Magic School. He and Phoebe had a relationship that lasted two weeks as Drake was destined to die.
One of Drake's best moments came in "The Seven Year Witch" when he encouraged the Charmed Ones to not give up on love. His spontaneous and passionate attitude came at the right time for Phoebe as she needed to see that she deserved happiness and love as much as her sisters did.
2 Cole Turner
Possibly the love of her life, Cole and Phoebe had a whirlwind of a romance. Cole was a half-demon who was first introduced to the show in season 3. He was hired by the Triad to kill the Charmed Ones but ultimately fell in love with Phoebe after his human side overtook.
Phoebe and Cole seemed to be in it for the long haul. However, this relationship was doomed for disaster when Cole became the Source. It didn't exactly scream happily ever after when Cole attempted to murder her sisters. As a result, Phoebe had to help Piper and Paige (Rose McGowan) vanquish her husband before he took over the world. At least he managed to redeem himself in the end.
1 Coop Halliwell
Was there any doubt that this would be the number one slot? However brief it may have been on the screen, Phoebe's relationship with Coop (Victor Webster) was her healthiest relationship of all.
Phoebe was introduced to the Cupid after the Elders sent him to help repair her faith in love. Coop attempted to set her up on several dates and even gave her advice on other magical matters. Although he developed feelings for her first, he continued to place Phoebe's happiness above his own. Luckily for him, his selfless and kind attitude was what attracted Phoebe to the Coop in the first place. The couple ended up getting married and had three kids together.