"He made it easy for me to walk away.”
Who: Singer, actress, author, and fashion designer Jessica Simpson, 42, and seven-time Grammy-winning musician John Mayer, 45.
How They Met: Back in 2005, Jessica and John met at Clive Davis’s pre-Grammy party, which she attended with her then-husband Nick Lachey. According to Jessica, John came up to her and complimented her new single “With You,” and from there, they began exchanging letters. By 2006, Simpson’s divorce from Lacy was finalized, and she and Mayer began a secret relationship.
They were spotted together on multiple occasions in early 2007 — including New York for New Year's Eve, Miami, and Italy — but neither would comment on their relationship status. Not until John confirmed they were together during a Grammys interview with Ryan Seacrest...in Japanese. John's riddle of a message ultimately translated to: "She’s a lovely woman, and I’m glad to be with her."
Jessica was equally as charmed by John in the beginning. “He’d walk into a room and pick up his guitar, and you’d swoon,” Simpson told People of their courtship. “I didn’t really know the man behind the guitar. And that was my mission.”
Little did Jessica know that mission would turn into a tumultuous, on-again, off-again romance that saw them break up and get back together nine times over four years.
Why We Loved Them: They were the Kim Kardashian and Pete Davidson of the early ‘00s. Jessica was the It Girl of Hollywood at the time, who had just gotten out of a toxic marriage, and John, a geeky guitarist (albeit a very charming one), was a welcome change of pace.
“He wanted to have all of me or nothing. Again and again, he told me he was obsessed with me, sexually and emotionally," she wrote in her memoir Open Book, adding: "I would get up to go to the bathroom, and John would ask, 'Where are you going?' “While I was married, my ex-husband couldn't be bothered to figure out what city I was in. It felt safe to be desired. I know John would never cheat on me, and that confidence was a new feeling for me."
As for John, when asked by Time Out New York what he thought about people calling him and Jessica an odd pairing in February 2007, he explained that it didn’t phase him.“I’m having the best time of my life, so if the names don’t make sense to people, that’s so small to me,” he responded.
When They Peaked: When a brunette Simpson and Mayer, attended the 2007 Met Gala as a couple. She wore a plunging beaded gown by Roberto Cavalli, while Mayer opted for a classic black suit without a tie.
The Breakup: Jessica and John called it quits for the first, but not the last time, in May 2007. They broke up and reunited on eight more occasions after the initial split. "We were great at intimacy. We were great at loving each other. That was easy, but the relationship was very complex," Jessica explained during an interview on Today in 2020. "And it was always on-again, off-again. On-again, off-again. And I went back close to nine times."
Jessica officially ended things in 2010 following John's derogatory comments about her in Playboy.
"That girl, for me, is a drug. And drugs aren't good for you if you do lots of them. Yeah, that girl is like crack cocaine to me," Mayer said during his infamous interview. "Sexually, it was crazy. That's all I'll say. It was like napalm, sexual napalm."
Reflecting on the interview a decade later, Jessica wrote, “He thought that was what I wanted to be called. I was floored and embarrassed that my grandmother was actually gonna read that," adding: "A woman and how they are in bed is not something that is ever talked about. It was shocking.” Discussing their sex life was the last straw for Simpson. "He was the most loyal person on the planet, and when I read that he wasn’t, that was it for me," she said. "I erased his number."
Where They Are Now: The same year Jessica ended her on-again, off-again romance with John, she met her current husband Eric Johnson. They were introduced by a mutual friend at a party and "connected on all levels." They married in 2014 and share three children — daughter Maxwell Drew 11, son Ace Knute, 9, and 4-year-old Birdie Mae.
In the years following her breakup with Mayer, Simpson shifted her focus from singing and acting to her fashion business. Jessica is the founder of a billion-dollar clothing empire, which she runs alongside her mom, Tina Simpson.
During his off periods with Jessica, Mayer dated Jennifer Aniston on and off from 2008 to 2009 before having a brief fling with Taylor Swift. He then got into a relationship with Katy Perry (his last serious girlfriend) in 2012, but the pair broke up two years later. As of right now, John is currently single.
John released his eighth studio album Sob Rock in 2021 and will soon embark on a world tour along with musical guest JP Saxe, in September.
#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.
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