Who Has John Mayer Dated? A Look Back at the Singer's Relationship History

John Mayer has dated a number of singers and actresses throughout his career.

The singer got candid in 2021 during an appearance on SiriusXM's Andy Cohen Live, telling host Andy Cohen that "there's one thing left [on his bucket list] and that's wife and kids."

He added, "That would be — that would complete all of it. And I thought about this as recently as last night. 'Cause my brothers are both married and have children."

Though Mayer has never married, he has been linked to some of Hollywood's biggest names, including Katy Perry and Jennifer Aniston.

In June 2025, Mayer opened up about how he still hoped to become a husband one day. "I would not date someone if it didn't have the upward mobility of becoming a marriage... every girlfriend would be a potential wife at this point," he said during a live taping of the Smartless podcast.

Most recently, Mayer was linked to influencer Kat Stickler after Deuxmoi reported that the two were spotted on two dates in a row. Reps for both Mayer and Stickler did not return PEOPLE's request for comment.

Here's a look back at John Mayer's dating history.

Jennifer Love Hewitt

Jennifer Love Hewitt briefly dated the singer in 2002.

Despite one of Mayer's biggest hits, "Your Body Is A Wonderland," being released a year before they dated, a rumor still circulated that the actress inspired the song.

She addressed the rumors in 2007, joking 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."

Mayer also clarified during a December 2022 appearance on Call Her Daddy that the song was about a high school romance, rather than any celebrity.

"That was about my first girlfriend," he said. "That was about the feeling, which I think was already sort of nostalgic. I was 21 when I wrote that song and I was nostalgic for being 16."

Jessica Simpson

Jessica Simpson and Mayer met at a Grammy party thrown by Clive Davis in early 2005, and they began seeing each other after her separation from Nick Lachey.

Though their romance quickly got serious, they ended their relationship in 2007.

Minka Kelly

Following his split with Simpson, the musician briefly dated actress Minka Kelly in 2007.

The two were first linked when they were spotted having dinner in Austin, Texas, in October 2007. They were seen together a number of times after that, including courtside at a New York Knicks game the following month.

However, their romance didn't last long, and they called it quits by January 2008. After the split, a source close to Kelly told PEOPLE, "Minka told a couple of friends that she and John had broken up, but she really didn't want to tell anyone."

Jennifer Aniston

After meeting at an Oscars party in 2008, Mayer and Jennifer Aniston were on-and-off for about a year.

By August 2008, things fizzled out for the pair. Mayer held an impromptu press conference at the time after leaving the gym in New York City, explaining, "I ended a relationship to be alone because I don't want to waste somebody's time if something's not right."

After their first split, they briefly reunited and stepped out to attend the Oscars together in 2009 where the Friends star was a presenter. However, they ended things again shortly after.

"They had some disagreements and decided to not continue to see each other," a source told PEOPLE at the time. "Jen is moving on with her life like she always does. She seems happy."

Taylor Swift

Taylor Swift and Mayer were first linked in 2009 after collaborating on "Half of My Heart" for Mayer's album Battle Studies. They performed the duet onstage in December 2009 at Z100's Jingle Ball in New York City, and were spotted enjoying dinner together in Nashville the following month.

After things ended between the couple in 2010, Swift released her third studio album, Speak Now, in October of the same year, which included a track titled "Dear John," about a relationship with an older man, reportedly written about her ex. She sings, "Don't you think nineteen is too young/ To be played by your dark twisted games / When I loved you so?"

When they dated in 2009, Swift was 19 and Mayer was 32. While the singer never confirmed if he was the inspiration behind her lyrics, Mayer publicly spoke about his feelings about them.

"It made me feel terrible," Mayer told Rolling Stone in 2012. "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."

Katy Perry

Mayer was first linked to Katy Perry in August 2012, but a friend of Perry's told PEOPLE that they were trying to take things slow at first.

"I don't think either of them are trying for anything serious right now. She's not talking like he's 'The One,' " the source shared. "She's comfortable around guys who understand the craziness of that world, which he definitely does."

However, things quickly heated up between the two after a brief break as they were spotted on multiple occasions, even attending President Barack Obama's inauguration in January 2013 together.

"I don't feel like I'm in a celebrity relationship," Mayer told CBS Sunday Morning in February 2013. "For the first time in my life I don't feel like I'm in a celebrity relationship. I really don't ... For me it feels like something that’s very human."

The two broke up the following month before getting back together in June 2013.

They continued the on-again-off-again pattern into 2015, when things ended for good.