John Mayer claimed in a recent podcast appearance on Call Her Daddy that he has always sought out long-term relationships with women, even if he still cultivated a reputation as a ‘womanizer’ and serial dater.

More recently, he has kept his romantic life fairly private, though he was seen getting close to former Mad Men star Kiernan Shipka in recent months.

The singer–songwriter, who balances his solo work with his second career as the lead guitarist for 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 has been 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 it was released, making it impossible. 

Jessica Simpson (2006–2007)

Physical attraction: Mayer raved about his sexual chemistry with Jessica Simpson in a raunchy interview with Playboy from 2010; seen in 2007 in NYC

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 she deleted his phone number in the wake of the interview. 

Minka Kelly (2007) 

Short-term: Mayer and Minka Kelly briefly dated in 2007, after his breakup from Simpson; seen in November 2007 in NYC

Mayer had a brief fling with actress Minka Kelly after his relationship with Simpson dissolved. 

Jennifer Aniston (2008–2009)

Star power: Mayer dated Jennifer Aniston on and off 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–off relationship with Friends star Jennifer Aniston. 

While speaking to Playboy after their split, he admitted to sleeping with multiple other women during their off period. 

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 has never confirmed that he is the subject; seen in 2009 in NYC

The musician dated fellow hitmaker Taylor Swift from 2009 to 2010.

Following the conclusion of their romance, she was rumored to write her popular song Dear John about him.

However, Taylor has never admitted 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 he wrote his 2017 song Still Feel Like Your Man about his relationship with Perry.

Kiernan Shipka (2020)

The guitar virtuoso has been rumored to be romancing the former Mad Men actress Kiernan Shipka, who is more than two decades his junior at 22.

The two were seen hugging after dinner and drinks in Hollywood in February 2022.

They were seen again nine months later having a dinner date in November.

After the two left in separate cars, they reported parked a few blocks from the restaurant so that she could get into his limo before being dropped off at her place. However, neither has confirmed the potential romance.