More than a decade after the scathing “Dear John,” John Mayer’s dating history is still heavily observed. The guitarist and songwriter is known for being a womanizer by the media in the path and many are wondering if he is still dating around?
In 2022, John Mayer went on the Call Her Daddy podcast to express his wants of marriage but assured he was not dating at the moment. “Dating is no longer a codified activity for me,” Mayer admitted on the podcast. “It doesn’t exist in a kind of—it’s not patterned anymore.”
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He continued, “I quit drinking like six years ago,” the Grammy winner went on to tell host Alex Cooper. “So I don’t have the liquid courage. I just have dry courage.”
He later went on to say, “Every relationship I’ve ever been in was devoted to the idea that this could go the distance,” he continued. “My entire life, today included, if you told me that I could have a great two months with someone but it would end on the first day of the third month, I would not be interested. I’ve always sought potential for a long-term relationship.”
When host Alex Cooper asked if he was afraid of commitment, he replied, “Of course. I want to get married. Nothing’s hotter to be than conflict resolution. I am horny for conflict resolution.”
So who has John Mayer dated? Read more to find out.
Jennifer Love Hewitt (2002)
John Mayer’s first public relationship was with actress Jennifer Love Hewitt. It was rumored that the song “Your Body Is a Wonderland” was written for Hewitt. In response to those rumors, Hewitt joked to Entertainment Weekly, “My body is far from a wonderland. My body is more like a pawnshop. There’s a lot of interesting things put together, and if you look closely you’d probably be excited, but at first glance, not so much.”
Jessica Simpson (2006)
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John Mayer dated Jessica Simpson in 2006 after her highly publicized divorce from Nick Lachey. Though it was pretty brief, Mayer had lots to say about his sex life with her in a 2010 Playboy interview. “That girl, for me, is a drug, he said. “And drugs aren’t good for you if you do lots of them. Yeah, that girl is like crack cocaine to me.” He then described his experiences with her as “It was like napalm, sexual napalm.”
Simpson opened up in her 2021 memoir and on the Tamron Hall Show about how she found the comments to be disrespectful. “I wouldn’t expect an apology. I don’t think there’s a need for an apology. I feel like people end up finding their way to let you know they’re sorry. And [Mayer] might not be sorry, and that’s okay. We were kind of, like, on-off, on-off at that time. But to talk about anybody sexually was kind of disrespectful, but that’s on him.”
Minka Kelly (2007-2008)
John Mayer briefly dated Minka Kelly from the fall of 2007 to early 2008. The split was amicable and Minka was shown being supportive of her ex by going to his concerts. “Minka told a couple friends that she and John had broken up but she really didn’t want to tell anyone,” a source told People at the time.
Jennifer Aniston (2009 – 2010)
John Mayer dated Jennifer Aniston from 2009 to 2010. After the relationship with the Friends star ended, he talked about the relationship with Playboy in 2010. “That woman was the most communicative, sweetest, kindest person. When people hear the record [Battle Studies], I hope the songs make them think about their lives, not my life. Like, when you listen to Coldplay, do you think about Gwyneth Paltrow? I don’t write songs in order to stick it to my exes. I don’t release underground dis tracks.”
He continued, “We just have a regard for each other’s feelings that is pretty intense. It’s been a deep relationship, and it’s no longer taking place at all. Have you ever loved somebody, loved her completely, but had to end the relationship for life reasons?”
Taylor Swift (2010)
Arguably one of the most famous relationships among millennial/Gen Z-ers, John Mayer’s relationship with Taylor Swift still affects Swifties to this day. They struck up a romance when the collaborated on his song “Half of My Heart.”
After their breakup, fans theorized that “Dear John” off her album Speak Now was based of the relationship. When the song initially came out, Mayer told Rolling Stone in 2012, “It made me feel terrible, because I didn’t deserve it. I’m pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do.”
“I never got an e-mail. I never got a phone call,” he recalled about how he figured out the subject of the song. “I was really caught off-guard, and it really humiliated me at a time when I’d already been dressed down. I mean, how would you feel if, at the lowest you’ve ever been, someone kicked you even lower?” When asked about the song’s line, “Don’t you think I was too young to be messed with?” Mayer says, “I don’t want to go into that.”
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“I will say as a songwriter that I think it’s kind of cheap songwriting,” he says. “I know she’s the biggest thing in the world, and I’m not trying to sink anybody’s ship, but I think it’s abusing your talent to rub your hands together and go, ‘Wait till he gets a load of this!’ That’s bullshit.”
In response to his reaction, Taylor Swift told Glamour, “How presumptuous! I never disclose who my songs are about,” and added that she did not want to hear his public response. “I know it wasn’t good, so I don’t want to know. I put a high priority on staying happy, and I know what I can’t handle.”
Weeks before the release of Speak Now (Taylor’s Version), Swift warned her fans about behavior when the record is released. “I was hoping to ask you, that as we lead up to this album coming out, I would love for that kindness and that gentleness to extend onto our internet activities,” Swift said, per fan-recorded videos from the show. “So what I’m trying to say is, I’m putting this album out because I want to own my music and I believe that any artist who has the desire to own their music should be able to. That’s why I’m putting out this album.”
She continued, “I’m 33 years old, I don’t care about anything that happened to me when I was 19 except the songs I wrote and the memories we made together. So what I’m trying to tell you is that I am not putting this album out so you should feel the need to defend me on the internet against someone you think I wrote a song about 14 million years ago when I was 19.”
Katy Perry (2012 – 2015)
John Mayer was in an on-and-off relationship with Katy Perry from 2012 to 2015. During one of their first breakups, Katy recalled to Rolling Stone, “I was madly in love with him. I still am madly in love with him,” she said. She continued, “All I can say about that relationship is that he’s got a beautiful mind. “Beautiful mind, tortured soul. I do have to figure out why I am attracted to these broken birds.”
Kiernan Shipka (2022)
John Mayer sparked dating rumors with Kiernan Shipka in late 2022. The two were seen leaving a restaurant together in Los Angeles, California, in February and November 2022.
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