Is John Mayer dating Kiernan Shipka? Full list of women the Hollywood playboy has been linked with

Back in February, John Mayer and Kiernan Shipka were seen sharing a hug at the well-known Tower Bar inside the Sunset Tower Hotel

Is John Mayer dating Kiernan Shipka? Full list of women the Hollywood playboy has been linked with
John Mayer's dating list - Kiernan Shipka, Jennifer Aniston, Katy Perry, and more (Getty Images - Matt Winkelmeyer, Sonia Recchia for Diageo World Class Canada, Leon Bennett, Dimitrios Kambouris for The Met Museum/Vogue)
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SANTA MONICA, CALIFORNIA: John Mayer was recently seen with Kiernan Shipka once again months after they were spotted sharing a hug. This time, Mayer and actress Shipka were seen having dinner at Giorgio Baldi in Santa Monica on Sunday, November 6, and for several hours. Onlookers claim that the American singer-songwriter even sang a few songs for the actress. This has certainly sparked romance rumors between the parties. 

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Daily Mail reports that the 45-year-old singer was seen entering Giorgio Baldi, a fine establishment on Sunday and was joined by the 22-year-old actress Shipka. They both grabbed dinner and entered the place at around 8.15 pm, only to leave around midnight. The 'Slow Dancing in a Burning Room' singer opted for a more casual look as he wore a black windbreaker over an olive shirt and grey cargo pants. On the other hand, Shipka, best known for her role as Sally Draper in the AMC drama series 'Mad Men', sported a trenchcoat and black trousers to complete her outfit. 

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The duo was seen leaving the hang-out spot separately and in their own vehicles, however, the outlet further reports that Shipka got off her vehicle after a while and got into John's black Chevy Suburban limo. Back in February, Mayer and Shipka were seen sharing a hug at the well-known Tower Bar inside the Sunset Tower Hotel. While the actress has been romantically involved with filmmaker Christian Coppola, Mayer himself boasts a line-up of some fine women he has dated. 

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Vanessa Carlton (2002)

Vanessa Carlton attends the 73rd Annual Tony Awards at Radio City Music Hall on June 09, 2019 in New York City.
Vanessa Carlton attends the 73rd Annual Tony Awards at Radio City Music Hall on June 09, 2019 in New York City (Jenny Anderson/Getty Images for Tony Awards Productions)

Two decades ago, Mayer and Vanessa Carlton were reaching the masses individually and were rumored to be dating. Carlton broke through the scene with her track 'A Thousand Miles' and the rumors of them dating started swirling. However, it did not last long as Mayer moved on to someone else. 

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Jennifer Love Hewitt (2002-2003)

Actress Jennifer Love Hewitt attends the launch party for Lifetime's new series
Actress Jennifer Love Hewitt attends the launch party for Lifetime's new series "The Client List" at Sunset Tower on April 4, 2012 in West Hollywood, California. (Photo by Frazer Harrison/Getty Images)

Right after Mayer released the second hit single from his first album in 2002, he was rumored to be dating the 'Ghost Whisperer' actress Jennifer Love Hewitt. It was also reported at the time that his track 'You’re Body Is a Wonderland' was dedicated to her. While the two dated, their relationship became too stressful to handle after Mayer hit the road for his tour. 

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Jessica Simpson (2006)

Jessica Simpson attends Create & Cultivate Los Angeles at Rolling Greens Los Angeles on February 22, 2020 in Los Angeles, California.
Jessica Simpson attends Create & Cultivate Los Angeles at Rolling Greens Los Angeles on February 22, 2020 in Los Angeles, California (Amy Sussman/Getty Images)

Jessica Simpson and John Mayer dated for a year. After the breakup, the singer, while talking to Playboy, compared Simpson to "crack cocaine" and claimed that "sexually it was crazy" and that "it was like napalm, sexual napalm."

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Cameron Diaz (2007)

Cameron Diaz arrives for the German premiere of the film 'Sex Tape' at CineStar on September 5, 2014 in Berlin, Germany.
Cameron Diaz arrives for the German premiere of the film 'Sex Tape' at CineStar on September 5, 2014 in Berlin, Germany (Sean Gallup/Getty Images for Sony Pictures)

Mayer, 29 at the time, and Diaz, 34, were seen in New York City after Mayer split with Simpson and Diaz split with Justin Timberlake. People reported back in 2007 that the couple was "all over each other" and "super flirty: at the Bowery Hotel. Once again the romance fizzled out in a couple of months. 

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Jennifer Aniston (2009)

Actress Jennifer Aniston (L) and musician John Mayer arrive at the 2009 Vanity Fair Oscar Party hosted by Graydon Carter held at the Sunset Tower on February 22, 2009 in West Hollywood, California.
Actress Jennifer Aniston (L) and musician John Mayer arrive at the 2009 Vanity Fair Oscar Party hosted by Graydon Carter held at the Sunset Tower on February 22, 2009 in West Hollywood, California. (Photo by Michael Buckner/Getty Images)

It was reported at the time that the couple dated on and off for almost a year before they called it quits for the greater good. In the same interview with Playboy, Mayer explained that he was disappointed with the breakup and that Aniston was, "the most communicative, sweetest, kindest person."

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Taylor Swift (2009)

Musicians John Mayer (L) and Taylor Swift attend the launch of VEVO, the world's premiere destination for premium music video and entertainment at Skylight Studio on December 8, 2009 in New York City.
Musicians John Mayer (L) and Taylor Swift attend the launch of VEVO, the world's premiere destination for premium music video and entertainment at Skylight Studio on December 8, 2009 in New York City (Dimitrios Kambouris/Getty Images for VEVO)

The good days in their relationship were quickly overshadowed by the controversy after their breakup. It was reported that Taylor Swift's song 'Dear John' was aimed at Mayer which explained how badly he treated Swift. Years later, Mayer told Rolling Stone that he felt humiliated and added, "I didn’t deserve it. I’m pretty good at taking accountability… It was a really lousy thing for her to do."

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Rashida Jones (2009)

Rashida Jones attends the 2022 Vanity Fair Oscar Party hosted by Radhika Jones at Wallis Annenberg Center for the Performing Arts on March 27, 2022 in Beverly Hills, California.
Rashida Jones attends the 2022 Vanity Fair Oscar Party hosted by Radhika Jones at Wallis Annenberg Center for the Performing Arts on March 27, 2022 in Beverly Hills, California (Frazer Harrison/Getty Images)

The actress, known for 'Parks and Rec' and 'The Office', was seen enough times with the singer to spark dating rumors. E! reported at the time that their relationship was completely platonic but their outings were enough to catch the media's attention. 

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Miley Cyrus (2010)

Miley Cyrus performs in concert during day one of Austin City Limits Music Festival at Zilker Park on October 1, 2021 in Austin, Texas.
Miley Cyrus performs in concert during day one of Austin City Limits Music Festival at Zilker Park on October 1, 2021 in Austin, Texas (Gary Miller/Getty Images for MC)

Somewhere between 2010 and 2011, there were heavy rumors that the 'Hannah Montana' actress was dating John Mayer. Glamour also reported that the duo was seen making out during the 2011 Grammys. One source told the publication, "At one point backstage, Miley was rubbing John's back and, when he thought no one was looking, he leaned over and kissed her!"

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Kim Kardashian (2010)

Kim Kardashian attends the FENDI 25th Anniversary of the Baguette at Hammerstein Ballroom on September 09, 2022 in New York City.
Kim Kardashian attends the FENDI 25th Anniversary of the Baguette at Hammerstein Ballroom on September 09, 2022 in New York City. (Photo by Sean Zanni/Getty Images for FENDI)

 

One time, the pair were seen partying together in New York City with a couple of friends and the media blasted the news that the two stars were hooking up. As per Page Six, "They brought along other friends, but the idea was to see if they would hit it off." Mayer tweeted at the time, "I see @kimkardashian at Sirius/XM and say hello like a gentleman and you want to spin a story at my expense? [Bleep] you!"

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Katy Perry (2012-2015)

Singers Katy Perry (L) and John Mayer attend the 55th Annual GRAMMY Awards at STAPLES Center on February 10, 2013 in Los Angeles, California.
Singers Katy Perry (L) and John Mayer attend the 55th Annual GRAMMY Awards at STAPLES Center on February 10, 2013 in Los Angeles, California. (Photo by Christopher Polk/Getty Images for NARAS)

 

After she finalized her divorce from Russell Brand, she set her eyes on John Mayer, and the pair dated for three years on-and-off. However, the romance couldn't last long once again for both parties due to hectic schedules and trust issues. Perry told Entertainment Weekly that they exchanged love letters long before their relationship went public.

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