Who: Golden Globe and Emmy-winning actress Jennifer Aniston, 50, and Counting Crows frontman Adam Duritz, 55.
How They Met: Not much is known about their reportedly "brief" relationship, but the pair met at some point in 1995, before she met and began dating actor Tate Donovan.
Why We Loved Them: There are scant details about their relationship out there (and only one or two public photos), but at the time, Friends had just taken off, and Counting Crows had just won two Grammys the year prior, making them a power couple early in their respective careers.
"Jen and Adam had become friends and they were hanging out there," Slavin said in an interview with InStyle. "Friends had just exploded and was massive, and Adam was in the biggest band in the country and his record was blowing up, so they were the biggest power couple."
The Breakup: Again, the nitty-gritty of their relationship remains shrouded in mystery, but we do know that Aniston went on to date Donovan after meeting him in 1995 through mutual friends (the first public photos of them came in early 1996).
Aniston hasn't really spoken about their relationship publicly, and Duritz has been similarly mum — though he once said in an interview regarding Aniston, "We never even slept together."
The kicker, however, is that he went on to date Courteney Cox — Aniston's Friends co-star and real life friend — in 1997. There aren't any public photos of the two of them together (the '90s were a simpler time), but he did seemingly confirm he dated both of them in a 2014 interview when asked about his relationships with both actresses.
"I don't like that it became the only thing they wrote, but that's their problem," he told Men's Health, referring to tabloid coverage on tidbits about his relationships. "It wasn't great for me, it wasn't great for my band. But it's nothing I did. I'm not gonna link people's idiocy to my choices, because those were perfectly reasonable choices. They were nice girls and I went out with them and that was that."
TBD on whether either of them inspired any Counting Crows songs.
Where They Are Now: Duritz went on to be romantically linked to Mary Louise Parker, and in 2009, dated Emmy Rossum for roughly a year. The two split in 2010, with Rossum telling reporters, "We're still very close friends."
Earlier this year, he made headlines when he shaved off his famous dreadlocks. He also started a Counting Crows podcast, in which he and music journalist James Campion discuss life, music, and "whatever comes into their large and incredibly handsome brains."
Aniston went on to date Donovan, and of course, became one half of Hollywood's golden couple when she began dating (and eventually married) Brad Pitt. Years after she and Pitt broke up, she married Justin Theroux, and they announced their split in February 2018.
After Friends's wild success, she moved onto the movie world, and in 2014, had a starring role in the drama Cake, for which she was nominated for a Golden Globe. She's making her big return to TV this fall in The Morning Show.