The Ex Jennifer Aniston Had To Work With On Friends During Their Breakup

Much has been made of Jennifer Aniston's relationship history, and it's hard not to see why. Over the years, she's been linked to fellow A-listers like John Mayer, Brad Pitt, Vince Vaughn, and Justin Theroux. Aniston's "Friends" counterpart, Rachel Green, also was linked to A-listers — well, characters played by A-listers, that is. Audiences saw Rachel date Tommy, who was played by Ben Stiller; Paul, who was played by Bruce Willis; and Gavin, who was played by Dermot Mulroney.

At a few points in the series, Aniston's real-life relationship history collided with Rachel's love life. Who could forget when Pitt popped up on an episode of Season 8 when they were still married? "Mr. Pitt was wonderful," Aniston said of his guest spot in an Access Hollywood interview years later. "Fantastic."

While Jennifer Aniston and Brad Pitt certainly seemed to enjoy working together on the show when they were still an item, it probably would've been a different story if Pitt was on the show in the wake of their split. Just ask actor Tate Donovan. 

Tate Donovan entered the "Friends" universe in Season 4 and stuck around for five episodes. He played Joshua, a boyfriend of Jennifer Aniston's Rachel Green. As fate would have it, Donovan and Aniston were in the middle of breaking up in real life: The two actors reportedly dated from 1995 to 1998. 

In 2024, Donovan shared with The Independent that he had a difficult time playing Aniston's character's boyfriend on "Friends," as their split was still very fresh. "It's like going to class when you're in high school and you've broken up with the girl who you sat next to and... argh, it's tough," he said. Donovan also noted that when he was first offered the part, he figured it might be a good way to move on. However, in a 2013 interview with HuffPost Live, he acknowledged how hard it was to keep it together on set. "I remember just getting back to my dressing room and just weeping," he said. 

In the aforementioned interview with The Independent, Donovan shared that the late Matthew Perry was his saving grace during his time on "Friends." "He was such a champion of mine. He was so sweet. He was the only one who called me when me and Jen broke up," Donovan said. "The O.C." star also noted that the rest of the cast was also very considerate of what he and Aniston were going through. "Everyone was so supportive, but it was hard," he said. As hard as it was, Donovan shared that he still admires the performance he was able to muster up. "When I look back on it, I'm like, "Wow, good for you, man. That was pretty good,'" he said. Talk about a bittersweet way to look back on a breakup.