Charmed: Phoebe’s Best and Worst Relationships, Ranked

Before Eric Dane McSteamed up Grey Sloan Memorial, before Julian McMahon made Miami beautiful, and before Nick Lachey was asked to stay out of Tree Hill, all three men fell under the spell of Charmed‘s Phoebe Halliwell. And they weren’t alone.

In her never-ending quest for love, Alyssa Milano’s character crossed paths (and occasionally swapped wedding vows) with a who’s who of 2000s TV, and each suitor left a profound impact on her heart. In the spirit of celebrating the ones that got away, TVLine is taking a stroll down memory lane to remember which of Phoebe’s relationships (including two demons and a cupid!) we’ll never forget.

(Side note: All eight seasons of Charmed are currently streaming on Peacock in glorious HD — albeit with that questionable new theme song — in case you feel like doing your own deep dive.)

Read on for our ranking of Phoebe’s seven most significant pairings, then drop a comment with your own thoughts on her love life.7

Dex Lawson (Jason Lewis)

Charmed Phoebe Dex

This relationship is lucky to even be included in this list, considering it happened while Phoebe was presenting as “Julie” after the sisters’ supposed death. Not to mention Phoebe only pursued Dex after having a premonition of them getting married — which turned out to be the result of a love spell cast by [pause for disgust] Billie.

Phoebe and Dex briefly considered staying married, taking an entire day to think it over, but no fan can say they were surprised when the couple decided to annul their mistake and never speak again.

Leslie St. Claire (Nick Lachey)

Charmed Phoebe Leslie

To his credit, Lachey did an admirable job of breathing life into the role of Leslie, a Ken doll hired to ghostwrite Phoebe’s advice column during her Season 7 sabbatical. Maybe Phoebe needed a fun rebound after ending things with Jason, but there was little for the viewers to invest in with this relationship — if you can even call it that. Their whole courtship felt faker than The Bay Mirror’s “Win a Date With Leslie” contest.

Besides, how could The WB have expected us to care about this couple when it didn’t even bother to use Leslie’s name in the promos? (“All this pressure can’t be good for Nick Lachey and Phoebe!” What does that even mean?)

Miles (Ken Marino)

Charmed Phoebe Miles

Much like Miles himself, this relationship only survived for a single episode, but the potential was clear. Phoebe had already been on several dates with Marino’s character by the time we met him in Season 5, and they seemed to make each other really happy. At least he got a breakfast muffin for the road — you know, before he died on it.

Coop (Victor Webster)

Charmed Phoebe Coop

It wasn’t until Phoebe stopped looking for love that she finally found it in the show’s final season. And given Phoebe’s obsession with love, coupled with her history of falling for supernatural gentlemen, it actually made perfect sense that she ended up with a literal cupid.

But would it have killed the writers to add a little more excitement into this romance? It’s almost ironic that Charmed did an episode where Coop helped Phoebe revisit her past relationships, as it only served to remind us how much more dynamic her love life used to be.3

Drake dè Mon (Billy Zane)

Charmed Phoebe Drake

A late entry in the race for Phoebe’s heart, Drake literally swept the lovesick witch off her feet (via an American in Paris-inspired dance number) within 10 minutes of meeting her. And even though he was secretly sent by Cole to restore her faith in love, their connection was genuine.

Sadly, by the time we finally appreciated the couple’s romantic potential, Drake’s time among the living was up. Even if you weren’t a fan of this pairing, you have to admit — that goodbye scene was a bummer.2

Jason Dean (Eric Dane)

Charmed Phoebe Jason

This coupling may have been a headache for The Bay Mirror’s human resources department, but it was easily the most successful relationship Phoebe ever had with a mortal. Not only did she and Jason have real chemistry, but he got along with her family (which can’t be said about every guy on this list!) and he was extremely supportive of her career.

Unfortunately, he wasn’t prepared to incorporate magic into his life. (And who could blame him after that whole Mata Hari incident?) Still, something tells us that if the universe had brought Jason and Phoebe back into each other’s lives a few years later, he might have had a change of heart. Oh, what could have been…1

Cole Turner (Julian McMahon)

Charmed Phoebe Cole

Come on, did you really expect to see a different face at the top of this list?

Phoebe and Cole’s star-crossed romance was on fire (albeit hellfire) from Day 1, setting into motion a three-season roller coaster we never wanted to end. From lovers to enemies to the co-rulers of hell, every phase of this relationship was legendary. Even their many breakups were epic, with Phoebe occasionally changing form — mermaid, banshee, you name it — as a result of her heartbreak.

We’re not saying that Phoebe and Cole were perfect together — he did try to kill her sisters on multiple occasions — but given everything they went through as a couple, they actually gave Piper and Leo a run for their money in the epic romance department.

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