“I Was Really Heartbroken” — I Can’t Believe Tate Donovan Got Through Filming Friends After His Breakup With Jennifer Aniston

Over its 10-season run, Friends became famous not just for its hilarious storylines and iconic catchphrases but also for the parade of A-list guest stars who made memorable appearances. Many of these guests played love interests for Friends' six main characters. From Bruce Willis’ tough-but-loving older partner for Rachel to Jon Favreau’s billionaire boyfriend for Monica, the sitcom consistently brought in big names to spice up the dating lives of Ross, Rachel, Monica, Chandler, Joey, and Phoebe.

One of the most interesting guest appearances came in season 4 when Tate Donovan played Joshua, a handsome personal shopping client who briefly dated Jennifer Aniston's Rachel Green. Before appearing in Friends, Donovan was no stranger to the screen, as he was featured in shows like Ally McBeal and even played the title character in Disney's animated film Hercules. However, what made his role especially noteworthy was that Donovan had recently ended a real-life relationship with Jennifer Aniston before filming his episodes. Despite the real-life tension, Donovan delivered a memorable performance as Joshua.

Tate Donovan Played Joshua In Friends

He Appeared In Five Episodes

Back in 1998, Donovan had a five-episode arc as Joshua Burgin in Friends. Joshua is one of the wealthy clients that Rachel encounters as a personal shopper at Bloomingdale's. He's recently divorced, and Rachel falls head over heels shortly after meeting him. She fails miserably in attracting Joshua's affections — even when she asks him to a basketball game, she fails to mention that one of the tickets is for her, and Joshua takes his nephew instead. Ouch.

Ultimately, Joshua and Rachel do not end up together, even after Rachel discusses marriage with him because she is devastated about Ross and Emily's wedding. Joshua cites his recent divorce as the reason for not wanting to pursue a romantic relationship. It doesn't help that she totally scares him away by answering the door in a wedding dress when he goes to see her.

Donovan Was Cast On Friends While He & Jennifer Aniston Were Breaking Up

He Called The Experience "Tough"

Donovan and Aniston had been dating for two years before they broke up during the former's stint on Friends. Yes, the couple was in the middle of a break-up, but Donovan was no stranger to the show. He said in an interview that he would go to Friends' tapings every Friday to support Aniston. He even pitched the idea of Rachel being interested in a man who doesn't like her back to the producers, and eventually played the role he had come up with.

The actor also went into more detail about working with his then-recent ex. He mostly described the experience as "tough" because so many people on the set knew both Donovan and Aniston personally. Donovan said (via The Independent):

“Yes, but it was very tough. Everyone was so supportive, but it was hard. 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.”

Donovan then discussed the support he received by late Chandler actor, Matthew Perry, saying:

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. And we ran into each other throughout the years, and he was always so incredibly supportive.

It meant so much to me [that he was kind on set] because I was really heartbroken, and you don’t know how well you’re doing, and you’re just trying to survive at that point. It’s such a tragedy that he had such a difficult time in life because, for me, Matt Perry was just… they all imitated his humour.

Rewatching Friends Gave Tate Donovan An Ego Boost

He Was Satisfied With How He Looked, For Sure

Although Donovan has moved on to a host of other projects, including The O.C. and the Oscar-winning film Argo, he still remembers his brief time on Friends. In 2024, Donovan recalled watching the beloved sitcom by accident while he was at a hotel. Of course, Joshua was in the episode he just happened to tune into to. But Donovan was proud of himself, particularly his looks, when he starred in Friends. He joked (via People),

“I was like, ‘Wow, I was really handsome at one point in my life…"

Today, Donovan continues to work in Hollywood with his most recent movie role was in the Oscar-winning film The Holdovers as Stanley Clotfelter. Although he might not be with Aniston anymore, the former Friends actor continues to have an impactful presence on both the big and small screen.