Tate Donovan Was Jennifer Aniston’s ‘Perfect Guy’: Romance Rewind 

Never mind Ross Geller; for a few episodes of Friends, it seemed like “Josh-ooh-ah!” might actually be the one for Rachel. In real life, though, Jennifer Aniston and Tate Donovan, who played her adorably oblivious curly-haired love interest during season four of the sitcom, were already breaking up. Let’s look back at Aniston’s relationship with the actor, now 61, who really seemed like he could be the one, just a few years before Brad Pitt was on the scene.

How it Began

In 1995, Friends was rapidly becoming the biggest TV show on the planet — but when Donovan was introduced to Aniston, now 55, via mutual friends, he had no idea who she was. “I’d never seen Friends!” he admitted in an interview with People.

Once Donovan — then a working actor before becoming a known name himself when The OC started in 2003 — had clocked that he was dealing with Jennifer Actual Aniston, he was reluctant to get into another high-profile romance following his four year relationship with Sandra Bullock. “Literally, our second date, there were video cameras everywhere, and I was like, ‘I’m out of here,’” he said.

A few weeks later, he changed his mind — well, she was Jennifer Actual Aniston, after all — and the pair started dating properly.

“On our first date, all we did was talk about our relationships,” Donovan told TV Guide in 1997, with Aniston adding: “We were like a mirror of each other.” There was one big difference, as Aniston said in the same interview: “I’m a New York City girl, and he’s a suburban Jersey boy.”

How Long it Lasted

The couple were an item for more than two years, and even moved in together, and even gave each other Irish commitment rings on their first anniversary in 1996.

Their biggest commitment? A dog! On their first Valentine’s Day together, Aniston went back to her Friends dressing room, expecting to find her boyfriend — but instead was met with an even cuter sight. “I opened the door, and this little puppy with a ribbon on poked his head out!” Aniston told People. The 9-week-old shepherd mix was named Enzo, and lifelong dog lover Aniston was obviously delighted.

Contrary to rumors, however, the couple were never engaged.

How it Ended

This is where things get awkward. In 1998, Donovan landed the role of Joshua in Friends — just as his real life relationship with Aniston was hitting the rocks.

“I’d been dating Jen for years, and I knew the cast,” he told The Independent in September 2024. “Every Friday night it was just like a ritual – I’d go over there and watch the taping, and it was always such a blast. Then Jen and I broke up, but we didn’t really tell anyone.”

Unfortunately for Donovan, that included the producers, who had come up with a great storyline for the pair. “I had mentioned to the producers that it’s always hilarious when Jen, who’s this gorgeous woman, is madly in love with somebody and the guy just doesn’t see it,” he said. “It cracked me up. I’d seen it when we first started dating – she did an episode where Rachel was on a date with a guy and the guy was just not into her, and she was falling all over herself. It works because that’s not really how she is in life, but she can act it so well. And so, the producers came to me and said, ‘Hey, we want you to do a five-episode arc where you guys are dating and you’re not really that into her.’ And I was like, ‘Oh, so you’re gonna do that thing.’ We were just breaking up and I, for some weird reason, thought that maybe working together would ease the breakup. Maybe we’d become friends quicker. I just wanted to go gently into the good night – we both did.”

Unsurprisingly, working together when they had literally just broken up was painful for all concerned. “It was very tough,” he said. “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. But it makes you a pro – it’s like, OK, we got over it. Nobody knows; the audience isn’t gonna know; the audience is gonna think just the opposite. When I look back on it, I’m like, ‘Wow, good for you, man. That was pretty good’.”

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Donovan said that one cast member in particular was a great source of emotional support at the time — the late Matthew Perry. “He was such a champion of mine,” Donovan recalled. “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 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.”

Donovan also spoke about the experience in an interview with Us Weekly in 2018. “It was just six episodes,” he said. “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. 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.”

Ultimately, though, the painful experience gave Donovan a lot of confidence in his career. “If you can go through a tough breakup, and still do your job, then you’re a pro,” he said. “It was good. It was really ultimately a great experience of how people can treat you really well, and you still do your job even though you’re sort of dying inside.”

In a 1999 interview with Rolling Stone, Aniston shot down rumors that her huge success had been a factor in their split – possibly sparked by their 1997 TV Guide chat in which Donovan remarked that she was “a lot wealthier” than him. “That wasn’t actually why we broke up,” she said. “Tate’s and my breakup had nothing to do with ego battles, wanting babies, not wanting marriage — all that stuff. None of it was accurate.”

What They Said About Each Other

In more recent years, Aniston has been pretty private about her relationships — but back in her twenties, she was much more open about her feelings. “He’s so real, so honest, so funny, so kind and considerate,” she told People in 1997, around the time the pair were house hunting together. “He’s all these things meshed into one perfect guy.”

In the same interview, the pair even hinted that they had marriage plans. “I definitely want to get married; she definitely wants to get married,” said Donovan. “There are no proposals or anything, not yet, but we definitely think about it.” Aniston was a little more coy, saying “You have to take your time to get to know someone.”

In TV Guide the same year, the pair were equally cute together. “She’s the most unbelievably great…actress!” said Donovan. “I was going to say, ‘thing that ever happened to me,’ but I was just trying to make it topical.” And when Aniston said she didn’t want to discuss their relationship, he quipped: “I’m more unabashedly in love with her, I guess!”

Aniston did, however, confirm that she was very happy with Donovan. “I like good guys,” she said. “Tate’s a good guy. I’ve been lucky that way. In high school I did go out with a guy who was mysterious and weird but would be nice when he was with me. I thought I’d be able to change him. And if you can be the one woman who can do that, how awesome are you? But it never happened.”

She added: “I’m definitely happy, I must say. Yeah, I’m the happiest now.”

What They Say Now

In his 2024 interview with The Independent, Donovan said he’s now — finally — able to watch those previously torturous episodes of Friends. “I was flipping through the channels at a hotel recently and I saw it, like, “Oh God, there’s Joshua.”,” he said. “I watched a bit of it and thought it was really good, and funny – for many years it was too painful for me to watch those scenes.”

And in an hilarious 2020 piece in Interview magazine, in which Aniston was grilled by Sandra Bullock, the pair talked about how they actually became friends via their mutual ex. “Introduced by our former boyfriend!” said Bullock. “I say ‘our’ because you and I both partook of this one human being.” Aniston confirmed: “Yes, we did. That’s a beautiful way of saying it. We both partook of Tate.” Bullock noted that the actor seemed to have a type: “Talented. Funny. Kind. Introspective. Generous.” Aniston added that the two superstar actresses were also both lovers of architecture and interior design.

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So, Aniston found a great friend via Donovan — but his main memory of the relationship is how insane Aniston’s fame was at the time, particularly when they traveled together. “English people in general are just obsessed with Friends,” he told The Independent in 2024. “It blows my mind. Jen and I dated for two years – when we went to England together, it was like being with a Beatle. We had to say we were having reservations at one restaurant and then go to another.”

Key Relationship Takeaways

More than five years her senior (he was 35 when they split; she was 29) and open about his dreams of getting married, it’s possible that Donovan was more ready to settle down than Aniston. So was he the one who got away, or the one before the one? Because the same year they broke up — 1998 — Aniston started dating Pitt, and we all know how that one ended.

Donovan, meanwhile, took a while longer to find love again, and this time followed his instinct to avoid another A-list relationship. He married writer Corinne Kingsbury in 2005, but they divorced three years later. He then wed Corry Scheuerman in 2015, and the pair are still together a decade on and have a family.

Over on Friends, Rachel and Joshua weren’t meant to be either — but in his 2018 Us interview, Donovan said he’s confident his alter-ego is enjoying life. “Joshua is happily married and has an 18 year-old-kid who is about to go to college,” he said. “He’s doing well. He’s doing good.”