In 1995, one year after the NBC series premiered, the Morning Show actress began dating Tate Donovan. The pair called it quits three years later, and while they were working through their split, they were given a romantic arc on Friends.

“I was just happy to be on the team. The only bummer was Jennifer and I were breaking up at the time,” the O.C. alum exclusively told Us Weekly in September 2018 of his turn as Joshua, one of Rachel Green’s love interests. “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.”

His character only lasted six episodes because it was “really painful” for the exes to appear on screen together. “The people that know that we dated think that we met on Friends,” Donovan joked. “But in fact we had dated for two years before then, and it was over by the time we were on Friends together.”

Though he had his ups and downs with Aniston, the Argo star said all six of the main Friends cast “were amazing” to him during his time on the show. “They were fantastic,” he gushed.

Donovan isn’t the only one of the Golden Globe winner’s beaus to have appeared on the legendary comedy. Brad Pitt made a brief appearance on Friends in 2001, playing a former high school classmate of Rachel, Ross Geller (David Schwimmer) and Monica Geller (Cox).

“Mr. Pitt was wonderful,” Aniston, who was married to the Fight Club star from 2000 to 2005, told Access Hollywood ahead of the May 2021 reunion special.

During the highly anticipated HBO Max event, Aniston’s former costars teased her over Pitt’s guest role. “Your fella Brad,” Schwimmer said as the cast reminisced on their favorite moments from the 10 years they worked on Friends.

Pitt eventually moved on with Angelina Jolie, from whom he split in 2016 after two years of marriage. Aniston, for her part, got remarried to Justin Theroux in 2015. They called it quits two years later.

“I would say we’ve remained friends,” Theroux told Esquire in May 2021. “We don’t talk every day, but we call each other. We FaceTime. We text. … I’m sincere when I say that I cherish our friendship. We can not be together and still bring each other joy and friendship. Also, she makes me laugh very, very hard. She’s a hilarious person. It would be a loss if we weren’t in contact, for me personally. And I’d like to think the same for her.”

Scroll down for a recap of the Friends cast’s dating histories through the years:

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This story originally appeared on: US Magazine - Author:Meredith Nardino