Jennifer Aniston and John Mayer in 2009 Kevin Mazur/VF/WireImage for Vanity Fair
Ah, Jen and John. Or was it John and Jen? The 2008 relationship between these two huge stars was so long ago and so short-lived in the grand scheme of things that it’s easy to forget what a huge hold they had over the pop culture consciousness at the time. Back then, though, the world was obsessed! Had Jennifer Aniston finally found lasting love? Was John Mayer ready to settle down? Well … no. Let’s see how it all played out …
How it Began
In true A-lister style, the pair met at an Oscars party in February 2008. Aniston was three years out of her marriage to Brad Pitt and had not long split from Vince Vaughn, while Mayer had most recently been linked with Minka Kelly, following his big relationship with Jessica Simpson. When they ran into each other a week later “that was that,” Aniston told Vogue later the same year, adding playfully that she “barely knew his music.”
Despite the nine year age gap (she was 39, he was 30) and Mayer having something of a reputation for dating famous women and then talking about it (a lot), we were all cautiously optimistic. At the very least, they looked gorgeous together.
More than two decades since scoring his big break, John Mayer is no stranger to making a public apology. Mayer became a household name in the early 2000s after releasing hit albums Room for Squares and Heavier Things. He’s earned critical acclaim — and won seven Grammy Awards — throughout his career, but he’s also […]
How Long it Lasted
Jennifer Aniston and John Mayer in 2008 Arnaldo Magnani
It all looked idyllic at first, with the couple spending time together in Europe and vacationing together in Miami, Orlando and Mexico, as well as attending a May 2008 wrap party together for Aniston’s movie, Marley & Me, and meeting up on Mayer’s U.S and U.K tours.
In August, after just a few months, they broke up for the first time. Mayer, as ever, was unable to contain himself when it came to talking about what had gone down. When confronted with the paparazzi on the streets of New York within days of the split, he delivered something of an impromptu press conference.
“It’s the most normal thing in the world,” he said. “There’s no lying, there’s no cheating, there’s no nothing. People are different, people have different chemistry, different lives. You’re either a cheater or you break up and I’m not the first one, I’m the second one. I ended a relationship to be alone, because I don’t want to waste somebody’s time if something’s not right.”
He went on: “Jennifer Aniston is the smartest, most sophisticated person I think I have ever met. I think she’s great. She’s one of the most lovely people I have ever met in my life. I’m truthful on the way into a relationship, truthful in the middle and truthful on the way out. I guarantee you there’s 20 per cent of people on this street that are in a relationship they wish they could get out of and don’t know how.”
Despite Mayer’s trademark blabbing likely not going down brilliantly with the typically more private Aniston, they reconciled a few weeks later in October and were spotted together at dinner in New York and celebrating Mayer’s birthday in Los Angeles. In November, at a charity benefit hosted by Alicia Keys, he said to People: “It’s really nice to have somebody in life have your back. That girl just knows me.”
Mayer was also by Aniston’s side when she celebrated her 40th birthday in February 2009, alongside friends like Courteney Cox and Sheryl Crow, and he was even reported to have written her a special song.
They were still going strong at the Oscars in February 2009, a year on from that first intro. “At some point, you feel comfortable and say, ‘This is the choice I want to make,” Mayer said in a radio interview at the time.
How it Ended
Sadly, by March 2009, just weeks after they had been all over each other at the Vanity Fair party, they were no more — and this time, seemingly, for good (but hey, never say never!)
While they both stayed quiet at the time, in the years that followed a picture began to form of their relationship, with those different life stages that everyone was worried about being discussed, including by Mayer himself, as a key reason for things not working out.
What They Said About Each Other
Jennifer Aniston and John Mayer in 2009 Kevin Mazur/VF/WireImage for Vanity Fair
In the Vogue interview that took place while they were on/off dating, Aniston addressed the age gap. “People need to mind their own business!” she said. “But you know, it isn’t designed. Love just shows up and you go, ‘Oh, wow, this is going to be a hayride and a half’.”
The actress also defended her man for lashing out during their first split. “He had to put that out there that he broke up with me,” she said. “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. 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.”
Jennifer Aniston was just 25 years old when she became a household name playing Rachel Green on Friends. After its September 22, 1994, premiere, viewers quickly fell in love with the stunning and funny star, and before she knew it, she was crowned America’s Sweetheart. With great fanfare came the not-so-great glare of the spotlight […]
What They Say Now
It was a few years before Mayer spoke about the relationship — but when he did, he couldn’t shut up. “I’ll always be sorry that it didn’t last,” he said in a 2010 Playboy interview (yes, the very same one where he notoriously called Jessica Simpson “sexual napalm”). “In some ways I wish I could be with her. But I can’t change the fact that I need to be 32. I want to dance. I want to get on an airplane and be like a ninja. I want to be an explorer. I want to be like The Bourne Identity. I don’t want to pet dogs in the kitchen.”
Wait, what? Who doesn’t want to pet dogs in the kitchen?!
Unfortunately, he didn’t stop there, then making Aniston sound out of touch when it came to tech. “If Jennifer Aniston knows how to use BitTorrent, I’ll eat my f—ing shoe,” he said, in a bizarre reference to the popular file-sharing software of the era. “One of the most significant differences between us was that I was tweeting. 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.”
Sounds like someone needs to cut down on their screentime.
When Jessica Simpson married Eric Johnson in July 2014, it seemed like it was for keeps — but, with the couple announcing their split about a decade later on Monday, January 13, we’re remembering the last time the singer endured a public breakup. That would be her on-off relationship with John Mayer, which ended in […]
He added, a little more sensitively, “Have you ever loved somebody, loved her completely, but had to end the relationship for life reasons?”
More recently, the pair have shown that there’s no bad blood between them, with Aniston occasionally engaging with Mayer’s social posts, even leaving crying-laughing emojis on one. See, she’s not such a technophobe after all!
Key Relationship Takeaways
Jennifer Aniston and John Mayer in 2009 Gregg DeGuire/FilmMagic
In the end, the timing was all off for these two — he was just too young for her, and their lifestyles weren’t compatible. Now that they’re both older (currently, 47 and 56 respectively) and have even more high-profile relationships behind them, from Justin Theroux to Taylor Swift, they would likely find more common ground. Two middle-aged people generally have way more relationship potential than a man in his early thirties and a woman turning 40.
Sure, they’re both currently single, but, you only have to look at the other world’s most famous Jennifer to know that going back to your ‘00s ex probably isn’t a great idea. So, shall we all agree that they should leave it at an annual emoji or two?