Throwback images of Jennifer Aniston and Tate Donovan

Aniston and Tate, who became her first serious boyfriend after shooting to primetime fame in Friends, met in 1995 after being introduced by mutual friends. Donovan admitted to not knowing who she was at the time — apparently he was one ot the few people who had never seen Friends.

Donovan may have been gun-shy at first, but his commitment didn’t stop at the Irish rings — he went all in, telling People in 1997, “I definitely want to get married; she definitely wants to get married. There are no proposals or anything, not yet, but we definitely think about it.”

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Donovan famously had a recurring guest role on Friends as a love interest for Aniston’s character, Rachel. But by then, the two had already called it quits — making for a very awkward filming experience.

“Those six people were amazing to me. They were fantastic. It wasn’t cliquey for me at all. I was lucky,” he said. “The good thing that came out of it was that everyone was really cool about it, and really as helpful as they could be. In other words, they were just compᴀssionate, very compᴀssionate about the whole breakup. It was sort of like I proved that, hey, I guess I’m a pro. If you can go through a tough breakup, and still do your job, then you’re a pro. 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.”

After their divorce, she married Justin Theroux, and they announced their split in February 2018.

Aniston’s career also moved out of the Friends zone and into the world of rom coms. In 2014, she had a starring role in the drama Cake, for which she was nominated for a Golden Globe.

After their split, he continued to pick up both movie and TV roles, and he was introduced to a new generation of viewers obsessed with a group of “friends” with his role in teen drama, The O.C.