John Mayer: 'I was just a jerk''
The infamous serial dater has also had relationships with a number of other big Hollywood names, including Jennifer Aniston, Jennifer Love Hewitt and Minka Kelly.
Now, however, the 35-year-old singer is recovering from surgery on his vocal cords and says he's looking to turn over a new leaf as he prepares for a return to the stage for the first time in two years.
"It's very liberating when you finally realize it's impossible to make everyone like you," he said in the interview. "I wanted everybody to like me. I thought I was one shuck and jive away in every direction."
It's a far cry from the Mayer who spoke candidly about his sexual relationship with Simpson, 32, in the March 2010 Playboy interview.
"Drugs aren't good for you if you do lots of them," he told the magazine at the time, comparing Simpson to "crack cocaine."
"Sexually it was crazy. That's all I'll say," he added of his relationship with the singer. The pair dated for about a year in 2006. "It was like napalm, sexual napalm."
Mayer also previously dated Taylor Swift, 23, who went on to write a song "Dear John," which fans speculated was about their ill-fated romance. In the June 2012 issue of Rolling Stone, Mayer criticized Swift's decision to write the lyrically revealing song.
"It made me feel terrible," he told the magazine, "because I didn't deserve it." The singers briefly dated in 2009.
"["Dear John" is] cheap songwriting," he continued. "It's abusing your talent to rub your hands together and go, 'Wait til he gets a load of this!' That's bulls--t."
Swift responded by calling Mayer "presumptuous… I never disclose who my songs are about," she told Glamour magazine in October 2012.