At this point, it must be every parent’s worst nightmare to discover that their offspring is dating that infamous scoundrel of a playboy, John Mayer. Despite his reputation for dating and dumping women constantly, he has managed to woo some of the most stunning and talented ladies in Hollywood.
It’s hard to resist his voice and his romantic lyrics. Probably, a lot of people he dates believe that they can change him, despite all of the glaringly obvious relationship red flags. Since he clearly has an aversion to commitment, he is a fun guy to date after a particularly bad breakup.
John has been very vocal when it comes to his views on marriage and long-term relationships. In 2017, he tweeted, controversially" “The word “commitment” is a funny one. Suggests eternal agreement. All commitment means is that you emotionally commit to an idea or person in that moment. You can exit a commitment at any time. Knowing that door is unlocked usually makes people stay in the room a lot longer.”
The known commitment-phobic may find, down the road, that he has missed a few dating opportunities with potential 'Mrs. Rights' because of his less-than-favorable reputation.
Today, let’s look at all the female celebs that John Mayer has pursued romantically.
15 The One About The Time He Dated Jennifer Aniston
Mayer and Aniston met at an Oscar party in 2008, and he became the perfect rebound guy for Jen to lick her wounds with, following the end of her marriage to Brad Pitt. The two dated and then broke up. They got back together and called it off for good in 2009. No one even wonders what went on with Mayer when the two were “on a break”.
14 A Swift Relationship With Taylor
The thing about dating other musicians is that they sometimes air their dirty laundry about you in their lyrics. Swift and Mayer had sung duets together and reportedly connected romantically when he was 32 and she was still a teenager. These rumors were confirmed when Swift released the 2010 song, “Dear John”. She sang memorable lines like, "Don't you think I was too young to be messed with?"
13 Jessica Simpson Romance
In 2006, Jessica Simpson and John Mayer rung in the New Year together. She later hung out with him while he toured around Florida. Soon, there was no denying that they were an item, and the two went public with their relationship. They broke up in the summer of 2007. Later, Mayer famously described their physical connection to Playboy Magazine as “sexual napalm" - an interesting choice of words.
12 The Kardashian Connection
Back in 2010, Kim Kardashian was looking for love (on camera, naturally) for her E! Series. While in New York, she painted the town red with John Mayer. Obviously, nothing came of their night together, but this was an interesting blip in pop culture that most of us basically totally forgot about.
11 Finding 'Love' With Jennifer Love Hewitt
Mayer dated Love Hewitt in 2002 and some believe that his song, “Your Body is a Wonderland”, was written about the curvy brunette. However, the song came out before they dated.
Apparently, they didn’t end things on the best terms, because Mayer was cruelly recorded saying, “If the tune WERE about her, it would be called "Your Body is a Disaster", according to Song Facts. Unnecessary roughness, John!
10 Cuddling With Cameron Diaz
Shortly after Cameron Diaz broke up with Justin Timberlake and John Mayer ended his relationship with Jessica Simpson, Cameron and John briefly found comfort in each other’s arms. Many describe their brief time together in 2007 as a fling; the famous duo was spotted on a date night in New York City.
9 Romantic Rumors With Rashida Jones
While he was believed to still be dating Jennifer Aniston, John Mayer attended a charity event at the Beverly Hills Chateau Marmont...with someone else on his arm. Reps denied any romantic connection, but the singer hit the red carpet with Rashida Jones. Rashida has been in a relationship with Vampire Weekend frontman, Ezra Koenig, since 2016, so that ship with John sailed away long ago.
8 Making Headlines With Miley Cyrus
Fresh out of her Hannah Montana years, Miley Cyrus was looking to distance herself from her syrupy-sweet, girl-next-door image. Being 18 and on the arm of a known playboy like John Mayer wasn’t a bad way to do that. The two were seen locking lips backstage at the 2011 Grammys, during a brief, but very noticeable, fling.
7 Long-Term With Katy Perry
Katy Perry and John Mayer have more than their music in common; they both have a history of on-and-off relationships with other celebs. Perry and Mayer first started dating in summer 2012 but split after just a couple of months. They then dated off and on, reuniting and breaking up many times. This all stopped in 2016 when Perry met Orlando Bloom.
6 Early Years With Vanessa Carlton
Remember Vanessa Carlton? Back in the early 2000s, she and Mayer were two young celebs looking for fame. The pair dated for a year and many have wondered if some of his first hits, like “A Thousand Miles”, were about Carlton. Vanessa has since gone on the record, to let the world know that John is, unsurprisingly, “a bad breaker upper”, according to ET Canada.
