Jennifer Aniston's Ex Was Miserable Working On Friends: "Dying Inside"

Highlights

• Jennifer Aniston's ex, Tate Donovan, struggled while appearing on 'Friends' with her due to their breakup.
• Donovan found it difficult to act like he was falling in love with Aniston's character while going through a real breakup.
• Despite the tough experience, Donovan eventually found love with Corry Scheuerman and the two got married.

Over the course of her time playing Rachel Green on Friends, Jennifer Aniston had her real-life significant others guest-star on the show with her. The most memorable occurred when Aniston was married to Brad Pitt. It was so memorable that during the Friends reunion, David Schwimmer brought up the appearance, albeit in an awkward manner.

For fans, however, Pitt guest-starring as Will Colbert, who hated Rachel in high school, was memorable because of what was expected of the character. Many thought Pitt would be a love interest, but he ended up being a completely different character entirely.

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Not all guest-starring roles with current or one-time significant others were as easy on set, however. In fact, one of Jennifer Aniston's exes was "dying inside" while appearing on Friends as Rachel's boyfriend. While the guest-starring gig was only six episodes long, it felt like an eternity for both actors until the storyline would end.

Jennifer Aniston And Tate Donovan Had Already Broken Up By The Time They Worked On Friends Together

Both Jennifer Aniston and Tate Donovan struggled through their scenes together on Friends

In 1995, before Aniston's face began to look different, Aniston and Tate Donovan started dating. Donovan has recently gotten out of a relationship with Sandra Bullock, and it does not appear that Aniston was dating a celebrity during that time period. However, the two hit it off and began a three-year relationship.

Unfortunately, the relationship did not last. But unlike exes being able to walk away from one another and give each other distance after a breakup, Donovan and Aniston were not able to do that. Donovan had just landed a six-episode guest-starring role on Friends as Rachel's potential love interest.

While Donovan and Aniston were able to remain professional, and Aniston gave her blessing for Donovan to appear on Friends, it was one of the hardest jobs that Donovan ever had.

"I was just happy to be on the team. The only bummer was Jennifer and I were breaking up at the time," Donovan explained. "And so that was tricky to sort of act, and act like we are just meeting each other, and falling in love, or whatever, interested in each other, when we’re sort of breaking up. That was just tough."

Donovan played Joshua, a personal shopping customer of Rachel's at Bloomingdale's. Through a series of shenanigans, Rachel was finally able to let her feelings for Joshua be known, but a relationship between the two characters ultimately did not work out.

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"It was just six episodes. I mean, only because we were breaking up. We were like, 'Hey, can we not keep doing this? 'Cause this is really painful and tough,'" Donovan said of how he and Aniston felt about working with one another at the time.

"The people that know that we dated think that we met on Friends. But in fact we had dated for two years before then, and it was over by the time we were on Friends together."

It helped that the cast of Friends was kind and compassionate to Donovan while he and Aniston were in the throes of their breakup. That way, both could be professional with one another and just do their best to get through the shoot. But at the end of the day, shooting scenes together was tough. Donovan recalled going back to his trailer and "weeping."

"It was horrible. It was so tough, man," Donovan said. "I just remember getting back to my trailer and just weeping."

While Donovan and Aniston broke up in 1998, it was not long before Aniston and Pitt started dating. Some started to wonder if there was anything between Pitt and Aniston that caused the breakup with Donovan to occur.

Jennifer Aniston Started Dating Brad Pitt Shortly After The Break-Up With Tate Donovan

The dating timelines appeared tricky from viewers' perspectives

After Aniston and Donovan broke up in 1998, Aniston made headlines for starting up a relationship with Pitt. While the timeline is close to the relationship with Donovan ending and the one with Pitt beginning, it does not appear that Pitt had anything to do with the split between Aniston and Donovan. Instead, the relationship had simply run its course.

Aniston and Pitt had met several years before they started dating. When they were both single in 1998, their agents took it upon themselves to set Pitt and Aniston up. The two dated quietly until making their relationship official in 1999.

The two would go on and get married and then subsequently divorced in 2005. While headlines liked to point to Angelina Jolie as the reason why the couple split, Aniston has admitted that sometimes, things just simply do not work out, versus blaming anyone for the end of the relationship.

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"We’re not in daily communication," Aniston says of Pitt. "But we wish nothing but wonderful things for each other. Nobody did anything wrong. You know what I mean? It was just like, sometimes things [happen]."

While Aniston has had a series of high-profile romances since, Donovan dealt with some heartbreak before he got his happily ever after. Though it took nearly two decades after dating Aniston, Donovan found love.

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Tate Donovan married Corry Scheuerman in 2015 and the two are still together today

After Donovan and Aniston broke up, Donovan was not in the headlines much for his personal life. But, in 2005, he married his girlfriend, Corrine Kingsbury, an actor, writer, and producer in Hollywood.

Unfortunately, after just three years of marriage, Donovan and Kingsbury divorced. There was no scandal around their divorce. It simply was because of "irreconcilable differences." Donovan paid a "one-time spousal support payment of $55,000" and the two ended their marriage.

The same year as his divorce, Dononvan met Corry Scheuerman. Scheuerman is in sports administration, which was a change from those whom Donovan had dated in the entertainment industry. In 2015, Donovan and Scheuerman made things official and got married.

The two were still together as of 2024, giving Donovan the happily ever after he was looking for.

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