Jessica Simpson, John Mayer broke up 9 times: Rewinding wild romance


John Mayer and Jessica Simpson broke up nine times during their relationship: Romance Rewind

Jessica Simpson and John Mayer in 2007 James Devaney/WireImage

When Jessica Simpson married Eric Johnson in july 2014 it seemed like forever – but, s the couple announced that they were separating About ten years later, on Monday, January 13, we remember the last time the singer experienced a public break. It would be her casual relationship with John Mayer, which ended in 2010, just months before she met Johnson. Let’s take a look back at what happened during the unlikely union — including nine divorces in four years.

How it started

Simpson, now 44, usefully told this story – and many others! — in his very interesting autobiography from 2020. An open book. When she first met Mayer, now 47, it was in 2005 and she was still married to him. Nick Lachey. Two, stylistically very different, musicians presented themselves at Clive Davispre-Grammy party, with Mayer complimenting Simpson on her hit ballad, “With You”. They corresponded occasionally, and then, when Simpson divorced Lachey in 2006 after four years of marriage, they started seeing each other secretly.

In early 2007, they were regularly seen together, but only when Mayer interviewed Ryan Seacrest at the Grammys that year to seemingly confirm their relationship … except, true to his quirky style, he did so in Japanese, uttering words that roughly translated to “She’s a lovely woman and I’m glad to be with her.” Oh-kaaaah.

How long did it take

The first separation of the couple was widely reported in May 2007, but soon they were back together. In fact, Simpson recalled while promoting her book that they broke up eight more times before finally calling it quits in 2010. “We were great at being intimate,” she said in 2020. Today interview. “We were great in love. That was easy, but the relationship was very complex. And it was always on-again, off-again, on-again off-again. And I’ve been back almost nine times!”

John Mayer and Jessica Simpson broke up nine times during their relationship: Romance Rewind

John Mayer and Jessica Simpson in 2005, the night they first met L. Cohen/WireImage for J Records

How it ended

Well, you might already know this part. In an interview with 2010 Playboy who quickly became infamous, Mayer was a little too revealing about his intoxicating relationship with Simpson, killing any chance of them meeting again for the umpteenth time — thank goodness!

John Mayer Most Controversial Moments Through the Years


Related: John Mayer’s Most Controversial Moments: ‘Sexual Napalm’ and Beyond

More than two decades since he hit his big time, John Mayer is no stranger to public apologies. Mayer became a household name in the early 2000s after releasing the hit albums Room for Squares and Heavier Things. He’s received critical acclaim — and won seven Grammy Awards — throughout his career, but he’s also (…)

“That girl is dope to me,” he said. “And drugs are not good for you if you take a lot of them. Yeah, that girl is like crack cocaine to me. Sexually, it was crazy. That’s all I’ll say. It was like napalm, sexual napalm. Have you ever said, ‘I want to end my life and just fucking snort you?’ If you charged me $10,000 to fuck you, I’d start selling all my s- just to keep fucking you.”

Understandably, the professionally clean-cut Simpson wasn’t thrilled to be described in such bleak terms (“I was devastated and embarrassed that my grandmother would actually be reading this,” she later said) and promptly cut the singer-songwriter out of her life. “I deleted his number,” she wrote in her memoirs. “He made it easy for me to leave. I did not accept his apology. I deleted all his contact information from my phone. I ended up with that man in a way I never thought possible. When he contacted me, I changed my number and email. Delete.” Boom — here’s that napalm in action!

What they said about each other

John Mayer and Jessica Simpson broke up nine times during their relationship: Romance Rewind

John Mayer and Jessica Simpson in 2007 Kevin Mazur/WireImage

Luckily, some of the couple’s other comments about their relationship were a little more grandmotherly.

“He’d walk into the room and pick up his guitar, and you’d pass out,” Simpson said People in 2020, recalling her first impressions of Mayer when they met. “I didn’t really know the man behind the guitar. And that was my mission.”

And in the conversation with February 2007 Time Out New YorkMayer said he doesn’t care if people think they’re an odd couple. “I’m having the best time of my life,” he said. “So if the names don’t make sense to people, that’s so little to me.”

What do they say now?

Because their relationship was so surprising and, ultimately, controversial, it’s a topic that’s come up many times in interviews over the years — as well as getting a full breakdown in An open book.

He wanted to have all of me or nothing, Simpson wrote. “He told me over and over that he was obsessed with me, sexually and emotionally. I would get up to go to the bathroom and John would ask me: ‘Where are you going?’. When I was married, my ex-husband couldn’t be bothered to figure out what city I was in. It was sure to be wanted. I know that John would never cheat on me, and that confidence was a new feeling for me.”

Simpson said Mayer’s intensely sexual comments about her felt like an unexpected betrayal from a man she thought she could trust to adore her. “He thought I wanted to be called that,” she wrote. “Woman and what they are like in bed is not something that is talked about. It was shocking. He was the most faithful person on the planet, and when I read that he wasn’t, that was it for me.”

While promoting the book, Simpson said AND! News that Mayer was forgiven… sort of. “I definitely don’t feel I’m owed a public apology,” she said. “You can’t take it back. I am also a very forgiving person, but I am also honest. So in a memoir, if I’m going to talk about things that hurt me, I’m going to be honest about it. And that was a period in my life when I was very manipulated and very much in love, or seemed to be.”

The older and wiser Simpson also now knows that her friends never agreed with the relationship. “He would dump me and then come back saying he found out he loved me after all,” she wrote. “I’ve always seen it as relentlessly pulling me in from the cold. Every time John came back, I thought it was a continuation of the love story, while my friends saw the guy coming back for sex with some stupid girl.”

John Mayer and Jessica Simpson broke up nine times during their relationship: Romance Rewind

Jessica Simpson and John Mayer in 2007 Paul Kane/Getty Images

Simpson also noted in the book that during the relationship she worried that Mayer was too smart for her — a source of sensitivity as she was caricatured as a “dumb blonde” at the time which, of course, we’ve since learned couldn’t be further from the truth.

“I constantly worried that I wasn’t smart enough for him,” she wrote. “He was so smart and treated the conversation as a friendly competition that he had to win.” She even said that she used to get friends to proofread her messages for him, in case he judged typos. “My anxiety would rise and I’d pour another drink,” she said. “It was the beginning of my reliance on alcohol to mask my nerves.”

Jessica-Simpson-through-the-years


Related: Jessica Simpson through the years: photos

God, how she has grown! Jessica Simpson has come a long way since she introduced herself to the world as a young singer with unforgettable pipes. After coming into the limelight, the musician went on to conquer reality TV, the fashion industry, motherhood and the Hollywood dating scene. Simpson left her mark with songs like “And (…)

Since then Playboy interview, Mayer was sensibly tight-lipped about his time with Simpson — but when An open book was published in 2020, Mayer’s close friend Andy Cohen started a thread with him. “I heard about it,” Mayer said of the memoir. “I heard some parts. But as Pee Wee Herman says in Pee Wee’s Big Adventure before the movie of his life starts playing at the end, he’s not watching the movie, and the reason he’s not watching the movie is, ‘I ain’t got to watch it, Dottie, I’ve lived it .’ And I think that’s far-sighted here.”

But has Mayer ever formally apologized for the “sexual napalm” comments that destroyed The Simpsons? Well, almost. On stage in Nashville in 2010he was filled with regret, explaining “In my quest to be smart, I completely forgot about the people I loved and the people who loved me” and saying he was in a “wormhole of selfishness, greed and arrogance”.

Later, in 2012, in an interview with NPR All things consideredoffered a similar explanation. “I had nothing to say,” he said. “I was going through a period in my life where I didn’t really want to share what was going on, but I didn’t want to be boring. When you’re just open, but not honest, then you start to freely associate garbage. That doesn’t mean I can go back and scrub it, but I understand it now.”

Key relationship data

John Mayer and Jessica Simpson broke up nine times during their relationship: Romance Rewind

John Mayer and Jessica Simpson in 2007 Kevin Mazur/WireImage

This relationship was actually a ticking time bomb. As Simpson herself said in her book: “He loved me the way he could and I loved that love for a very long time. Too long. And I went back and forth with him for a long time. But it controlled me.”

Some people even believed that Simpson changed her image for Mayer, dyeing her signature blond brunette to please him – but she claims that’s not true. “He didn’t make me a brunette,” she said Allure after their separation. “John doesn’t get credit for making me a brunette. He’d like to think so, but he doesn’t deserve the credit.”

With both stars seemingly single now, we doubt Simpson will be unblocking Mayer’s number anytime soon. Because ultimately, as she says, “that was Jess in her 20s.”

Now, as a 44-year-old mother of three, she knows better — and as for Mayer? He hadn’t acted so recklessly since then, so maybe they both learned something.



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