John Mayer claimed in a recent podcast appearance on Call Her Daddy that he’s always sought long-term relationships with women, even though he’s still built a reputation as a “womanizer” and serial dater.
More recently, he’s kept his romantic life fairly private, though he’s gotten close to former Mad Men star Kiernan Shipka in recent months.
The singer-songwriter, who combines his solo work with his second career as the lead guitarist of the Grateful Dead spin-off band Dead & Company, has dated a long list of A-list stars.
Below are some of the most high-profile women Mayer has dated over the years.
Jennifer Love Hewitt (2002)
Rumors: Jennifer Love Hewitt is rumored to be the subject of Your Body Is A Wonderland, but the song was written before she ever dated Mayer; seen in 2002, the year they dated
Hewitt has long been rumored to be the subject of Mayer’s hit single Your Body Is A Wonderland, though the two didn’t start dating until a year after its release, making it impossible.
Jessica Simpson (2006-2007)
Physical attraction: Mayer raved about his sexual chemistry with Jessica Simpson in a raunchy 2010 Playboy interview; seen in 2007 in New York
Mayer and Simpson dated from 2006 to 2007, but he didn’t have much to say about their romance until an infamous 2010 Playboy interview in which he referred to her (affectionately) as “sexual napalm.”
She later claimed that she deleted his phone number after the interview.
Minka Kelly (2007)
Short Term: Mayer and Minka Kelly dated briefly in 2007, after his split from Simpson; seen in November 2007 in NYC
Mayer had a brief affair with actress Minka Kelly after his relationship with Simpson broke up.
Jennifer Aniston (2008-2009)
Star Power: Mayer dated Jennifer Aniston off and on from 2008 to 2009. The two are reportedly still on friendly terms; seen in 2009 in LA
One of Mayer’s most high-profile romances to date was his on-again, off-again relationship with Friends star Jennifer Aniston.
While speaking to Playboy after their split, he admitted to sleeping with multiple other women during their time off.
However, the two are reportedly still friends.
Taylor Swift (2009-2010)
Superstars: Taylor Swift reportedly wrote her breakup song Dear John about her brief fling with the guitarist, though she’s never confirmed he’s the subject; seen in 2009 in New York
The musician dated fellow hitmaker Taylor Swift from 2009 to 2010.
After the end of their romance, she was rumored to write her popular song Dear John about him.
However, Taylor has never admitted that the song is specifically about Mayer.
Katy Perry (2012-2014)
Immortalized: Mayer said he wrote his 2017 song Still Feel Like Your Man about his relationship with Perry from 2012 to 2014; seen in January 2014 in LA
One of Mayer’s longer public relationships was with another musician, Katy Perry, whom he dated from 2012 to 2014.
He later said that he wrote his 2017 song Still Feel Like Your Man about his relationship with Perry.
Kiernan Shipka (2020)
The guitar virtuoso is rumored to have a crush on former Mad Men actress Kiernan Shipka, who, at 22, is more than twenty years his junior.
The two were seen cuddling in February 2022 after eating and drinking in Hollywood.
Nine months later, they were seen again at a dinner party in November.
After the two left in separate cars, they reported parking a few blocks from the restaurant so she could get into his limo before being dropped off at her home. However, neither has confirmed the potential romance.
