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John Mayer’s Dating History: A Timeline of His Exes and Relationships!

What’s the real score between John Mayer and the female celebrity he was recently seen with? Fans were immediately pushed into a social media frenzy.

The “Chilling Adventures of Sabrina” actor Kiernan Shipka was spotted socializing with the “Never Gonna Be Alone” singer, according to ET Online.

According to reports, the couple dined at Santa Monica, California’s Giorgia Baldi, a popular Italian eatery among celebrities.

According to pictures that have gone viral online, the Dead & Company member was wearing sweatpants, a black jacket, and a pair of white sneakers for their night out.

His buddy, on the other hand, was dressed in a wool coat, matching slacks, and wine-red heels.

Mayer and Shipka spent more than four hours inside the Italian eatery, according to sources who were there at the time. At one point, after a few drinks, the singer serenaded the Netflix star. Here is the list of John Mayer’s girlfriends.

Famous women who were once John Mayer’s girlfriends

The singer of “Slow Dancing in a Burning Room” has dated a lot of women in the past. Vanessa Carlton, best known for her smash song “A Thousand Miles,” is the first.

Before Mayer began dating the actress Jennifer Love Hewitt, the duo allegedly dated briefly in 2002, according to More. “Your Body Is a Wonderland,” one of the singer’s best-known songs, was purportedly written with the celebrity in mind.

Though we are unsure if they truly dated, there have been speculations that the British model and actress Rhona Mitra hooked up with Mayer for a short while. Both sides made an effort to conceal their liaison.


One of Mayer’s many casual relationships was with Life Happens actress Milana Vayntrub. Vayntrub was only 19 when the 28-year-old artist was supposed to be hooking up with her, so it’s obvious that Mayer prefers them young.

Following their breakup with Nick Lachey, Jessica Simpson dated Mayer for almost a year. When Mayer compared Simpson to “crack cocaine” in an interview with Playboy soon after their breakup, the tabloids erupted. Moreover, he continued, “sexually, it was wild” and “it was like sexual napalm.” 

Cameron Diaz had recently broken up with Justin Timberlake when Mayer ended things with Jessica Simpson, and the two were momentarily seen fawning. What a great time to meet someone new! A source verified that the couple was dating after they were spotted together in New York City, although their relationship fizzled out very quickly.

Prior to his breakup with her to be with Jennifer Aniston, Derek Jeter’s ex and Friday Night Lights alum Minka Kelly had a casual relationship with Mayer. How do they still maintain their friendship? We’ll never find out.

Before calling it quits, the on-again, off-again pair dated for almost a year. Apparently, Mayer still felt heartbroken about their breakup years after writing “Shadow Days” about Aniston. He told Playboy, “That woman was the most talkative, loveliest, friendliest person.” It is possible that Jen was the one who escaped.

Scheana Marie claimed otherwise, but Mayer categorically denied any history with her. When the man was 23 years old, Just Jared questioned John about his kissing prowess in a video interview. She replied gushingly that she thought his lips were attractive. During the whole conversation, she kept making vague references to the two of them getting close, but no one knows for sure if that actually happened.

Naturally, Mayer is only one of the numerous awful boyfriends that hurt T-feelings. Swift Rumors that Swift’s song “Dear John” was actually written about Mayer began to circulate ‘after their divorce. Swift mentions in the song how “John” mistreated her and destroyed her heart. Even yet, she criticizes him for his “dark, twisted ways.” Poor T never seems to have any luck.

Later, Mayer said to Rolling Stone that he felt “very humiliated” by the song. I didn’t deserve it, he later said. I’m fairly adept at accepting responsibility. She did a terribly bad thing by doing that. Whatever gets you to sleep, buddy.

Actress Rashida Jones from Parks and Recreation was frequently spotted out and about with Mayer, which led to relationship speculations. Even though their relationship was entirely platonic, sources tell E!, it managed to garner media attention. Eventually, the rumours died down.

According to Glamour, the “Wrecking Ball” singer Miley Cyrus briefly dated Mayer before she met Liam Hemsworth. That may help to explain why, in 2014, Cyrus seriously dissed Katy Perry over her connection with John Mayer. Perhaps she still had some grudges.

While Kim Kardashian was filming an episode of Keeping Up With the Kardashians in 2010, the couple was spotted having fun together in New York City. Both individuals, according to Page 6, invited pals along to check if there was any spark between them.

Reena Hammer, a British makeup artist, dated Mayer briefly in 2010, but their romance was not long-term. They abruptly parted ways, and Hammer afterward dated Jonathan Rhys Meyers from The Tudors.

From 2010–2015,  “Dark Horse” singer Katy Perry moved on to Mayer not long after concluding her divorce from Russell Brand. She revealed to Entertainment Weekly that the couple had written each other love letters before going public with their relationship. Aw!

However, this love affair, like all of John Mayer’s romances, came to an end. The pair broke up after three years of an intermittent relationship because of schedule conflicts and concerns with trust. Even so, Perry is having a great time right now. She was just spotted having fun at Coachella with Orlando Bloom. Girl, you rock!


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