Jennifer Aniston and John Mayer

Who: Golden Globe and Emmy-winning actress Jennifer Aniston, 50, and 7-time Grammy-winning singer-songwriter John Mayer, 41.

How They Met: The unlikely duo struck things up at an Oscars party in February 2008. Aniston admitted she “barely knew his music” at the time, and that the romantic momentum really began when they “ran into each other a week later, and that was that.” They split in August of that year, reunited with a public flourish at the 2009 Oscars, and split once more just one month later.

Why We Loved Them: We just wanted to see Jen happy and thought maybe, just maybe, the impetuous and notoriously flirtatious singer could be of assistance.

When They Peaked: John didn’t, but Jen did — when she was discussing how great a mess he’d made, ironically. Regarding breakup no. 1 (and the rant Mayer gave in which he compared ending things with the Friends alum to burning the American flag), Jen told Vogue, “He had to put that out there that he broke up with me. And especially because it's me. It's not just some girl he's dating. I get it. We're human. But I feel seriously protective of him and us. Trust me, you'll never see that happen again from that man."

"And it doesn't take away from the fact that he is a wonderful guy,” she continued, “We care about each other. It's funny when you hit a place in a relationship and you both realize, We maybe need to do something else, but you still really, really love each other. It's painful. There was no malicious intent. I deeply, deeply care about him; we talk, we adore one another. And that's where it is." No wonder Jen’s exes love her.

The Breakup: After Jen and John sang their ultimate swan song, Mayer delivered what was essentially part II (and later III) of his rant, waxing poetic about his ideal “Joshua Tree of vaginas” to Rolling Stone and revealing that his relationship with Jen didn’t “arc over the horizon” and wasn’t his “ideal destiny.”

Just one month later Playboy published a wildly controversial interview with Mayer, in which he implied that Aniston (eight years his senior) was too old for him and that her reluctance to adapt with the technological times put a strain on their relationship.

"I'll always be sorry that it didn't last. In some ways I wish I could be with her. But I can't change the fact that I need to be 32," he said.

Clarifying rumors that he and Aniston split over Mayer’s excessive Twitter use, the singer said, “If Jennifer Aniston knows how to use BitTorrent, I’ll eat my f—king shoe.” Nice. “One of the most significant differences between us was that I was tweeting,” he continued. “There was a rumor that I had been dumped because I was tweeting too much. That wasn’t it, but that was a big difference. The brunt of her success came before TMZ and Twitter. I think she’s still hoping it goes back to 1998. She saw my involvement in technology as courting distraction," he explained.

In the end, though, no matter how technologically averse Aniston is, Mayer admitted there was love there. “Have you ever loved somebody, loved her completely, but had to end the relationship for life reasons?" he asked the Playboy reporter.

Despite their somewhat tempestuous history (or, y’know, Mayer’s), the singer made an appearance at the actress's 50th birthday bash this past weekend.

Where They Are Now: After splitting from Aniston, Mayer went on to have high-profile flings with Taylor Swift and Katy Perry, but it seems he’s since learned from the error in his public romancing ways. Though there was speculation about his relationship with Halsey in late 2018, the musical pals both deny that they share anything more than a friendship.

Aniston began dating Justin Theroux after breaking things off with Mayer. The pair wed in 2015 and announced their separation just two years later in February 2018.

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