Jennifer Aniston Received the Most Adorable Valentine's Day Gift from Then-Boyfriend Tate Donovan

Who: Golden Globe nominee and Emmy winner Jennifer Aniston, 50, and Emmy winner Tate Donovan, 55.

How They Met: 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.

Before that, Aniston dated Counting Crows frontman Adam Duritz, and Donovan dated another A-list actress: Sandra Bullock. In fact, that relationship had him on edge about dating Aniston, who was only getting more famous.

“Literally, our second date, there were video cameras everywhere, and I was like, ‘I’m out of here,'" he told People at the time. A month after that date, they split up. But three weeks later, he changed his mind, and the two exchanged Irish commitment rings on their first anniversary.

When They Peaked: 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.”

For what it's worth, Aniston played it coy, adding, “There’s nothing to report. You have to take more time to get to know someone.”

Why We Loved Them: Apparently, Donovan was committed enough to buy Aniston a puppy — a 9-week-old named Enzo. The story goes that on Valentine's Day in 1996, she had just finished a scene for Friends and went back to her dressing room, expecting to find Donovan.

“Then I opened the door, and this little puppy with a ribbon on poked his head out," she said.

The Breakup: 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.

“I was just happy to be on the team. The only bummer was Jennifer and I were breaking up at the time,” he recalled to Us Weekly in 2018. “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 client of Rachel's at Bloomingdales, who she develops a major crush on.

“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. “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.”

Still, he looks back on the experience as whole with fondness, even if he felt like he was "dying inside" at the time.

“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 compassionate, very compassionate 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.”

Where They Are Now: Aniston, of course, went on to be one-half of Hollywood's golden couple with Brad Pitt.

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.

Donovan later married writer Corinne Kingsbury, in 2005, and they divorced in 2008.

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.