John Mayer turned 42 on Oct. 16, 2019, and as the "Battle Studies" star sings, "It's been a long time since 22." Since his 20s, John has dated many of Hollywood's finest, so in honor of his big day, Wonderwall.com is taking a look back at all the ladies he's romanced over the years. Keep reading to take a walk down memory lane…
Jennifer Love Hewitt, dated in 2002
John Mayer started dating '90s and '00s darling Jennifer Love Hewitt in 2002. Their romance has lived on in infamy thanks to a very persistent rumor that holds Jennifer is the inspiration for his hit "Your Body Is a Wonderland." But the song was actually released before they dated, and Jennifer has since reflected on the misconception, telling People that if the tune WERE about her, it would be called "Your Body is a Disaster." We doubt that!
Vanessa Carlton, dated in the early '00s
In the early '00s, Vanessa Carlton and John Mayer were just two kids climbing the Billboard charts: She was at the top of her game with the hit song "A Thousand Miles," while John was pumping out hits like "No Such Thing" and "Your Body Is a Wonderland." They got together and reportedly dated for about a year before calling it quits. Vanessa, who's bisexual, later called John a "bad breaker-upper."
Rhona Mitra, dated in 2005
Perhaps mistaking himself for Bailey Salinger (Scott Wolf's character on "Party of Five"), John Mayer ended things with Jennifer Love Hewitt and started dating Rhona Mitra, who played Bailey's post-J.Love girlfriend on the hit show. Creepy, right? No word on how the two hooked up, but she's a gorgeous British actress, and he loves beautiful brunettes, so it definitely makes sense.
Jessica Simpson, dated in 2006-2007
John Mayer became a prime target for the paparazzi in 2006 when he and Jessica Simpson spent New Year's Eve together in New York City and smooched in Miami's South Beach before she followed him on tour around Florida. A lifetime supply of magazine photos later, they finally admitted they were together. While it only lasted until June 2007, John later told Playboy that their physical romance was red-hot, calling Jessica "sexual napalm" and comparing her to "crack cocaine."
Cameron Diaz, dated in 2007
Cameron Diaz and John Mayer had a fling back in 2007 when they were both fresh out of high-profile relationships — she had just split from Justin Timberlake and he'd called it quits with Jessica Simpson. The stars hooked up in New York City over dessert at the French-Vietnamese restaurant Indochine and cocktails at the Bowery Hotel. According to People, they were "super flirty."
Minka Kelly, dated in 2007-2008
After splitting with Jessica Simpson, John Mayer frolicked around Los Angeles with "Friday Night Lights" star Minka Kelly in the winter of 2007 and 2008. They hit some Hollywood hotspots, and once again, the musician found a woman to watch him perform, but they called it quits because he just didn't want a serious relationship… or did he?
Jennifer Aniston, dated in 2008-2009
The Internet practically exploded when John Mayer flew to Miami to hang with Jennifer Aniston (whom he'd met at an Oscar party in 2008) while she filmed "Marley & Me." Whether he wanted a serious relationship or not, the world wasn't going to have it any other way, and he was soon pegged as the guy who would save Jen from her post-Brad Pitt loneliness. They broke up for a while then got back together, only to end things again in 2009. "One of the most significant differences between us is that I was tweeting," he told Playboy. "The brunt of her success came before TMZ and Twitter. I think that she's still hoping it goes back to 1998."
Rashida Jones, linked in 2009
After John Mayer and Rashida Jones were spotted together at the Chateau Marmont and at a Beverly Hills charity event in 2009, a new couple alert was in effect for Los Angeles County. Reps called it a coincidence — especially since the Jennifer Aniston relationship was still up in the air — but ultimately, it just seemed like too much of a coincidence. And this is John Mayer we're talking about…
Scheana Marie, dated in 2009
Nowadays, we know Scheana Marie as Scheana Shay, star of Bravo's "Vanderpump Rules" — but back in 2009, she was a waitress-actress who happened to catch John Mayer's eye. Unfortunately for John, the future reality star talked to tabloids. The then-24-year-old beauty told YoungHollywood.com, "I love his personality… he's funny… He can be, like, a dork." And after that interview, John reportedly stopped talking to Scheana for good. Oops!
Kristin Cavallari, almost dated in 2009
John Mayer's reputation preceded him in 2009 when he crossed paths with reality star Kristin Cavallari. They met briefly and he asked her out, but the star of "The Hills" told Ryan Seacrest on KIIS FM that she shot the playboy down. "I didn't want to be another notch on his belt," she said.
Taylor Swift, dated in 2009
Rumors circulated that Taylor Swift and onetime duet partner John Mayer hooked up in 2009 when he was 32 and she was just a teenager. She confirmed it by releasing the 2010 song "Dear John," which featured lyrics like, "Don't you think I was too young to be messed with?"
Kim Kardashian West, sort of dated in 2010
Just before she met husband No. 2, Kris Humphries, Kim Kardashian West was on the hunt for a new man while filming her E! series in New York City in 2010. Kim and John Mayer reportedly hit the town together for a night. As we know, it didn't end up working out… but bet you didn't remember these two ever had a fleeting love connection!
Shenae Grimes, rumored to have dated in 2010
Star magazine sources alleged that John Mayer and "90210" star Shenae Grimes were a secret couple back in 2010, but the actress quickly squashed those rumors. "According to Star magazine John Mayer and I are in secret sexy cahoots," she tweeted. "How wonderful for me… if wonderful meant embarrassing." So cold!
Miley Cyrus, rumored to have dated in 2011
If the tabloids are to be believed, Miley Cyrus and John Mayer were a thing in 2011. Miley was only 18, but the two were reportedly spotted kissing backstage at the Grammy Awards that year. One tabloid even suggested she was carrying his love child.
Renee Zellweger, dated in 2011
Both Rene Zellweger and John Mayer had a history of hopping in and out of celebrity relationships, so it was only a matter of time before they eventually hooked up. He dated Jennifer Aniston, who dated Bradley Cooper, who dated Renee, so they were already just a few degrees of separation apart. But Page Six finally made it a direct connection, reporting that they were "discreetly" dating in May 2011.
Katy Perry, dated off-and-on from 2012-2015
John Mayer and Katy Perry seemed to be a match made in musical heaven. The famous pair started dating in the summer of 2012 but split that August. From there, they were on-again, off-again lovers for almost two years before ending things in February 2014… except that wasn't it for John and Katy! The two reunited once more in January 2015 and continued to keep people guessing until early 2016, when Katy officially moved on with Orlando Bloom. John opened up about the relationship on "The Ellen DeGeneres Show" back in 2013, shedding light on why the hot-and-cold pair were always so mysterious. "Listen, it was a very private relationship going in. It was a private relationship during, and it's a private relationship still," he said.
Demi Lovato, linked in October 2016
John was linked to Demi Lovato in October 2016. Us Weekly reported that multiple witnesses spotted the two musicians hanging out together — her in a leopard-print jacket and matching miniskirt; him in a Hawaiian-print jacket and ripped jeans — at West Hollywood hotspot Catch on Oct. 22. "John had his arm around Demi and was whispering sweet nothings into her ear," an eyewitness told Us Weekly. "She was into it," the witness added. "They weren't making out or anything, but she was giggling the whole time." The pair — she's 15 years his junior — "chatted it up for over an hour," a second source told the magazine, adding that John was also gushing that the pop star "has one of the greatest voices." John and Demi have known each other since 2009 when they co-wrote a song for her sophomore album together.