John Mayer's Dating History: Jennifer Aniston, Katy Perry and More

A-list love life! John Mayer is arguably one of the biggest heartthrobs in Hollywood and has romanced some serious A-listers. Although he has seemingly stepped out of the dating pool in recent years, the musician has wooed celebs like Jennifer Aniston, Katy Perry, Cameron Diaz and Taylor Swift throughout the years.

Nowadays, the “Heartbreak Wayfare” artist has a good sense of humor about his past. When a fan asked on Instagram how he’s still single, the “New Light” singer simply responded, “Google me.” Needless to say, his love life is under constant speculation, and he’s even shut down relationship rumors with Kourtney Kardashian and Halsey.

The Grammy winner previously addressed the rumblings of a blossoming romance with the Keeping Up With the Kardashians alum long before she married husband Travis Barker and joked that he thought the news was coming from the famous family’s inner circle.

“I’ve got to be honest with you, [a] little suspicious about the origin of the story. I’m not sure the calls are not coming from inside the house on this one,” John confessed to Andy Cohen on SiriusXM’s Radio Andy in May 2019. “I will say, if the call is coming from inside the house, it’s diabolical and genius.”

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What really happened? The two did chat at a gathering, but it’s not quite what you think. “I ran into Kourtney at a party that I kind of crashed. It was a GQ party, and I crashed it toward the end,” he explained. “I ran into the bass player from the Scorpions … And then Kourtney Kardashian walks up and I said, ‘Kourtney, walk away. He’s the bass player from the Scorpions, he’s going to try to get you in a video.’ … All I did was save Kourtney Kardashian from being in a video with the bass player from the Scorpions.”

If you read past reports, John got a reputation for using a supposed pickup line that was a bit cringy. However, the “Carry Me Away” singer definitely wanted to clear the air on that. “The only part that made me upset to any degree was that somebody said that when I saw Kourtney, I said, ‘It was sweet serendipity running into you,’ which I would never say,” he divulged. “I didn’t say that because that’s hyper-corny.” Whew, that’s truly a relief.

So, John and Kourtney may not have been an item but he’s dated a slew of other famous women along the way. Keep scrolling to see his impressive dating history!

Katy Perry

The “Firework” singer dated the guitar guru on and off from 2012 to 2015. Their romance left an impression because Katy ranked John at the top spot when asked who was best in the bedroom between him, Diplo and her current fiancé, Orlando Bloom. Although that’s high praise, the Dead & Company artist was less than impressed.

“I don’t have a cool enough thought for you,” he told Rolling Stone about his exes claims at the time. “I’ve hacked this game. I pay very little of the price of fame now. I get to play the music that moves me the most. I’m having the time of my life … I remember 32. I don’t wanna do it again.”

Taylor Swift

Their tumultuous relationship from November 2009 to February 2010 ended with Taylor’s song “Dear John,” which had some incriminating lyrics about an older guy misleading a younger woman romantically.

In it she sang, “Dear John, I see it all, now it was wrong/ Don’t you think nineteen is too young /To be played by your dark twisted games, when I loved you so?/ I should’ve known.”

“I never got an e-mail. I never got a phone call,” John told Rolling Stone about the song in 2012. “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?”

John said he felt “really humiliated” by Taylor’s song and that “I didn’t deserve it.” But when the reporter asked John directly about the lyric, “Don’t you think I was too young to be messed with?” the crooner replied, “I don’t want to go into that.”

Their messy uncoupling is still hard for some fans to get over. John joined TikTok in March 2021 and was met with an army of Swifties shading him on the platform. He seemingly responded to the negative comments with a video that showed him mumbling and nodding like he was pretending to be lectured. “POV: You’re berating me and I’m hearing you out,” he wrote.

John again defended himself when some Swifties came after him following the November 2021 release of Red (Taylor’s Version), despite “Dear John” appearing on Speak Now. When one person told him via DM that they wished he would die,” John calmly responded, “I’ve been getting so many messages like these the past couple days,” and added, “I’m not upset, I just tend to have a curious mind and feel compelled to ask. Do you really hope that I die?”

Jessica Simpson

After her divorce from Nick Lachey, the pop star dated John for about a year in 2006. After their romance fizzled out, the artist gave some very dirty details about their sexual chemistry.

“That girl is like crack cocaine to me,” John said about Jessica in Playboy. “Sexually it was crazy. That’s all I’ll say. It was like napalm, sexual napalm. Did you ever say, ‘I want to quit my life and just f—king snort you? If you charged me $10,000 to f—k you, I would start selling all my s—t just to keep f—king you.'”