rundown
John Mayer has been dating for over 20 years. John Mayer’s past relationships include Jennifer Love Hewitt, Jessica Simpson, Jennifer Aniston, Taylor Swift, and Katy Perry. These days, Mayer is enjoying his single life, but he said he still “strongly wants to get married.”
John Mayer has long been one of the most recognizable names in music, known for his Grammy-winning songs and high-profile love life. Since rising to fame in the early 2000s, the singer-songwriter has dated some of Hollywood’s biggest names, from actors to fellow musicians, and many of those romances have inspired some of his songs.
Mayer has been candid about his relationships over the years. “I definitely want to get married,” he said on the podcast Comfort Food with Kelly Rizzo in January 2024. “I really want to get married, if only my wife would know in her heart, ‘John will know what to do,'” he said. I think being relied on at that level is the hottest thing in the world to me. ”
Below is a complete timeline of his love history, from his relationships in the early 2000s to his most recent relationship in 2025.
jennifer love hewitt
Mayer and the Who Knows What I Did Last Summer actress briefly dated in 2002. Although their relationship was short-lived, there were rumors that his 2001 hit song “Your Body Is a Wonderland” was about her. In October 2007, Hewitt told Entertainment Weekly magazine, “My body is far from a wonderland. My body is more like a pawn shop. It’s got a lot of interesting things put together, and if you look closely you’ll probably be excited, but it’s not as much as it seems at first glance.”
Mayer later set the record straight himself. On Call Her Daddy in December 2022, he said the song was about his high school girlfriend, not a celebrity. “It was about my first girlfriend,” he explained. “I was 21 when I wrote this song, but I missed being 16.
jessica simpson
Mayer and Jessica Simpson began dating in 2006 after she broke up with Nick Lachey. Their relationship lasted on and off for about a year, but it became one of the most discussed romances after he described her as a “drug” in a 2010 Playboy interview.
“He loved me as much as he could, and I loved that love for a very long time,” Simpson later wrote in her 2020 memoir, Open Book.
“I was just an idiot,” Mayer said at the time. He told CBS Sunday Morning in 2013 that he learned from those mistakes.
minka kelly
After breaking up with Simpson, Mayer briefly had a relationship with Friday Night Lights actress Minka Kelly in 2007. The two were spotted together several times that fall, including at a New York Knicks game.
However, by early 2008, the relationship ended. A source said at the time that Kelly “really didn’t want to tell anyone” about the breakup and that the two were “still friends.”
jennifer aniston
Mayer began dating Friends star Jennifer Aniston in early 2008 after meeting at an Oscar party. Their relationship was on and off for about a year.
According to Us Weekly, when the pair broke up that summer, Mayer spoke directly about the breakup while speaking to paparazzi in New York. “It’s the most normal thing in the world,” he said. “There’s no lying, there’s no cheating, there’s nothing. Everyone is different, their compatibility is different, their lives are different. You either cheat or you break up. I’m not the first cheater, I’m the second cheater.”
Aniston spoke out about the relationship later that year, telling Vogue magazine: “We care about each other. It’s funny when a relationship stalls and you both realize that you need to do something else. And yet you still really, really love each other. It’s tough. There was no malicious intent. I care deeply, deeply for him. We talk and we adore each other.”
Mayer reflected on their relationship in a 2010 interview with Playboy magazine, saying, “I’m always disappointed that it didn’t last longer. In some ways, I wish I could have been with her.” I can’t change the fact… The ability to be deeply involved with someone is an old soul. But at 32 years old, it just comes out of me when I don’t think it’s coming.” I don’t want to fly on a plane and look like a ninja, or be like The Bourne Identity, or pet a dog in the kitchen. ”
taylor swift
In 2009, Mayer collaborated with Taylor Swift on her song “Half of My Heart,” and a short-lived romance with the then-19-year-old began soon after. Their relationship reportedly inspired Swift’s 2010 song “Dear John.”
Mayer told Rolling Stone magazine in 2012 that he was surprised by the song. “I felt terrible,” he said. “Because I wasn’t responsible for it. I’m good at taking responsibility now, but I didn’t do anything to deserve it. It was really awful for her.”
She added that she “never received an email or phone call” beforehand, adding: “It really caught me off guard and was really humiliating even though I was already dressed up.”
Swift did not specify the subject matter of the song, telling Glamor magazine at the time, “How presumptuous! I never reveal who my songs are about.”
katy perry
Mayer and Katy Perry began dating in 2012 after Perry divorced Russell Brand. Their relationship lasted on and off for about three years.
“Actually, I’m dating someone I like,” Perry told W magazine in 2013. “I’ve had a crush on him for a long time.”
That same year, she told Ellen DeGeneres, “We have a lot of fun. We have music as our understanding and love for each other. We connect and he’s doing the same thing, so it’s like he understands what I’m doing…He gets it.”
They collaborated musically on Mayer’s 2013 song “Who You Love,” and their chemistry was evident in both that song and its accompanying video. “It’s really authentic,” Meyer told ABC News. “There’s no script in that video other than putting a bull in the middle of the desert.”
Perry told Vogue in 2013, “I was madly in love with him. I’m still madly in love with him. All I can say about that relationship is that he has a beautiful heart. A beautiful heart, a troubled soul. You have to understand why I’m drawn to this broken bird.”
Their relationship included several public breakups and reconciliations. In a 2013 interview with Marie Claire, Perry explained, “Taking a vacation with my boyfriend wasn’t what I wanted. Searching within myself to find out what was going on with me was like being poured cold water on me.” She added, “That led me to a new awakening. I realized that without self-love, I wouldn’t be able to have the love that I wanted.”
The couple appeared together at multiple events.
However, by the summer of 2015, media reported that they had officially broken up for good.
Mayer later reflected on their relationship in a 2017 interview with The New York Times, admitting that his song “Still Feel Like Your Man” was written about Perry. “Who else would you be thinking of?” he said. “By the way, this is a testament to the fact that I haven’t dated too many people for the last five or six years. That’s been my only relationship. So I’m like, give me this.”
kat stickler
In October 2025, Mayer was linked to influencer and comedian Kat Stickler after unidentified celebrity gossip outlet DeuxMoi published a photo of the two dining together in New York City. Us Weekly later confirmed the rumor, citing a source who said Mayer “sought her out and tracked her down.”
“Kat had just broken up with someone she had been dating for a few months and thought it would be fun to date again and was interested in John,” the source explained. “He is actively pursuing her, inviting her to places and texting her frequently. She is interested and is watching to see how it goes.”
The source added that Stickler, who became famous for her comedy TikTok, “doesn’t think it’s going to be a serious relationship” and that they are “enjoying it.”
Shortly after the reports surfaced, Stickler shared a casual TikTok post confirming that he was single, suggesting their relationship was casual.
On November 1, 2025, witnesses told DeuxMoi that Mayer and Stickler were again seen eating at Italian restaurant Torrisi in New York City.
