Ranking the Real-Life Romantic Partners Who Guest-Starred on ‘Friends’

Some of them were more than ‘Friends’ (sorry)
Ranking the Real-Life Romantic Partners Who Guest-Starred on ‘Friends’

Friends had a lot of famous guest stars during its run, from Oscar winners to blockbuster comedy stars to Jean-Claude Van Damme, for some reason that presumably made sense back in 1996. Also, for what may or may not have been carpool-related reasons, several Friends guest stars were romantically involved with the cast. So how do they stack up against each other? While we can't force them to fight to the death in gladiatorial combat, at least we can rank them...

Brad Pitt as Will

Unless you have a crippling phobia of US Weekly covers, you’re probably aware that Jennifer Aniston and Brad Pitt started dating back in 1998 and got married in 2000. This explains why Pitt showed up in the 2001 episode The One With the Rumor as Will, an old high school friend who was conspicuously never mentioned before or after, who hates Rachel with a passion.

This one is at the bottom of the list, not because Pitt is bad per se, but because the ripped movie star mining his character’s struggles with weight for laughs isn’t great. At least he thankfully didn’t don a Fat Monica like fat suit for flashback scenes, as Entertainment Weekly reported at the time. And this is before we get to the heart of the storyline involving Will spreading a rumor that Rachel is intersex, which was condemned by the Intersex Society of North America for being hurtful and offensive. 

Tate Donovan as Joshua

The former star of Love Potion No. 9, Tate Donovan, was briefly engaged to Aniston before they ultimately called it off… right before he appeared in several episodes of Friends as her new love interest Joshua. Donovan’s okay, but his chemistry with Aniston isn’t great — probably because being forced to fake a romantic relationship with your ex-fiancée isn’t so much fun, and he was reportedly "dying inside" during their scenes.

David Arquette as Malcolm

Courteney Cox married her Scream co-star Arquette in 1999, but while they were still dating during Friends’ third season, he showed up as Malcolm, Phoebe’s not-so-subtle stalker who turns out to be her sister Ursula’s stalker. Because he’s charming and handsome, Phoebe starts dating him, despite the glaring fact that he’s a gigantic creep.

Julia Roberts as Susie

Matthew Perry convinced Roberts to appear in a special Super Bowl episode of Friends (thanks to his trusty fax machine), and the two started dating soon afterward — she was even grilled about it by David Letterman.

It’s weirdly an inverse of Chandler Bing’s arc in the episode. In real life, Perry and Roberts traveled to New Mexico together, where she introduced him to her family, while on Friends, Chandler is forced to strip naked and abandoned in a restaurant bathroom by Roberts’ character, Susie. Which is fine because Chandler Bing is a monster.

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