The Truth About Jennifer Aniston And John Mayer's Relationship

Given John Mayer's extensive dating history over the years, it may be difficult to recall just exactly who the beloved musician has been in a relationship with. After all, it was Mayer himself who once told The New York Times, "I'm a young guy. I like girls. I want girls to like me. I want to make music and be thought of as attractive." 

So it shouldn't come as a surprise that the "Your Body Is A Wonderland" singer's list of past relationships include the likes of Taylor Swift, Jessica Simpson, Katy Perry, Minka Kelly, and of course, "Friends" alum Jennifer Aniston

While Aniston has had her fair share of long-term, high-profile relationships with A-listers – Vince Vaughn, Justin Theoreux, Paul Rudd, and (who could ever forget) Brad Pitt (via Us Weekly) to name a few – the "Morning Show" star's on-again, off-again relationship with Mayer was the talk of the tabloids between 2008 and 2009. In the years since their split, Mayer and Aniston have openly spoken about their relationship together, and some of the comments they've made about one other are actually pretty shocking.

John and Jennifer met at an Oscars party

After meeting in February 2008 at an Oscars party, the pair hit it off right away. Jennifer Aniston and John Mayer ran into each other about a week later, the "Friends: The Reunion" star told Vogue, and "that was that," (via E! News). 

When the couple first split later that year, Mayer took it upon himself to talk about their breakup to the media, at one point telling the paparazzi, "If you guys are going to ... run every lie under the sun ... have me as a man who ended a relationship," (via CheatSheet).

In a December 2008 Vogue profile, per People, Aniston opened up about their highly publicized split, telling the outlet, "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." She continued, "There was no malicious intent. I deeply, deeply care about him; we talk, we adore one another. And that's where it is."

John seemingly regrets breaking up with Jennifer

In an interview with Playboy (via Us Weekly), John Mayer opened up about splitting with Jennifer Aniston — someone who he described as "the most communicative, sweetest, kindest person" (via CheatSheet) — telling the outlet, "That pearl of possibility that lives in your heart when you meet somebody you want to know more about has such a different molecular density than everything else that you have to pursue it. And I wouldn't undo it, man. Because if it had worked out, I would have reaped the benefits. I would be sitting here saying, 'What I have when I go home is the thing I've always wanted.'"

However, in that same Playboy interview, the "Daughters" crooner seemingly took a weird dig at Aniston's age (she's eight years older than him) while simultaneously pining over her, saying, "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," (via Marie Claire).

Mayer also told Rolling Stone in 2012, via E! News, that he'd "never really gotten over the split" and called it "one of the worst times of my life." 

Jennifer and John have remained friends over the years

During an Instagram Live in 2020, John Mayer was sharing a story about the late Bill Withers, telling his followers, "For as long as I have been a fan of his or knew him personally, I never saw the man compromise on his principles — ever. Whether he was speaking to you or speaking to an interviewer 15 years ago, 14 — 13 years ago, everything he said is useful. 4% of the things that I say are useful. One hundred percent of the things he said were useful" (via Harper's Bazaar). 

Jennifer Aniston reportedly responded to her ex's story with three cry-laughing emojis, signaling that there's no bad blood between the former lovers. 

In 2020, which marked over a decade since their final split, a source opened up to Us Weekly about Mayer and Aniston's current relationship, telling the outlet, "Jen and John have a nice friendship John has a deep admiration and respect for Jen. Whenever they talk or are out together it's always friendly and nice. There is definitely no weirdness between them."