John Mayer has one of the most storied dating histories in Hollywood today.
Mayer’s history of dating famous women began early in his career.
Next up was actressJennifer Love Hewitt, who he dated from 2002 to 2003.
The next few years saw Mayer making the most of his bachelor status.
He was dating around, spotted with many different models and actresses, but none for too long.
They first started seeing each other shortly after her divorce from Nick Lachey in 2006 (perRefinery29).
Simpson revealed that they broke up nine times and each time, Mayer ended things with her by email.
She claimed that was the last straw in their back and forth.
“I erased his number.
He made it easy for me to walk away.”
Mayer had no problem moving on to another major name whose relationships were constantly making headlines: actressJennifer Aniston.
Mayer and Aniston only lasted about a year in their relationship before splitting.
“I’ll always be sorry that it didn’t last.
In some ways I wish I could be with her.
But I can’t change the fact that I need to be 32,” he said.
The brunt of her success came before TMZ and Twitter.
I think she’s still hoping it goes back to 1998.
She saw my involvement in technology as courting distraction.
And I always said, ‘These are the new rules.'"
2009 saw Mayer have some flings with some famous names.
He was linked toVanderpump Rulesstar Scheana Marie and actress and writer Rashida Jones.
In 2009, he began dating fellow singer-songwriter Taylor Swift.
She was 19 years old at the time, while he was 32 (perEvening Standard).
Swift wasn’t shy about the fact that the breakup was not amicable.
That was far from Mayer’s last famous fling, however.
After Swift, he was linked to Miley Cyrus, Kim Kardashian, and Reena Hammer (perMore).
There was one more famous songstress in his sites, however.
Mayer and Perry waited some time to confirm that they were an item.
She discussed it when talking about the track “Legendary Lovers” off her albumPrism.
The two reportedly split three different times between 2012 and 2016.
“I was madly in love with him.
I still am madly in love with him,” Perry toldRolling Stoneduring one of those break-ups in 2013.
I do have to figure out why I am attracted to these broken birds."
Since their split, Mayer hasn’t dated much.
“Who else would I be thinking about?”
Mayer toldThe New York Times.
That was my only relationship.
So it’s like, give me this, people."
Perry has moved on with actor Orlando Bloom.
The two welcomed a daughter, Daisy Dove, in August 2020 (perToday).
