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Jessica Simpson, John Mayer Broke Up 9 Times: Wild Romance Rewind


John Mayer and Jessica Simpson Broke Up Nine Times During a Relationship: Rewind Romance

Jessica Simpson and John Mayer in 2007 James Devaney/WireImage

When Jessica Simpson married Eric Johnson in July 2014, it seemed as if it was for keepers — but, with the couple announcing their split about a decade later on Monday, January 13, we remember the last time the singer suffered a public breakup. That would be her lasting relationship with her John Mayer, which ended in 2010, just a few months before she met Johnson. Let’s look back at what went down during the unlikely union — including nine splits in four years.

How It Started

Simpson, now 44, has helpfully told this story – and many others! — in his highly revealing 2020 autobiography, Open Book. When she first met Mayer, now 47, it was in 2005 and she was still married Nick Lachey. The two musicians, who are very different in style, were introduced in Clive Daviespre-Grammy party, with Mayer praising Simpson on his hit ballad, “With You”. They became occasional reporters and then, when Simpson divorced Lachey in 2006 after four years of marriage, they started seeing each other secretly.

By early 2007, they were seen together regularly, but only when Mayer was interviewed by Ryan Seacrest at the Grammys that year he apparently confirmed their relationship… except, true to his quirky style, he did it in Japanese, saying words that roughly translated to “She’s n lovely woman, and I’m proud to be with her.” Oh-kaaaay.

How Long It Lasted

The couple’s first split was widely reported in May 2007, but they were soon back together. In fact, Simpson recalled while promoting her book that they broke up eight more times before he finally called it quits in 2010. “We were great at intimacy,” she said in a 2020 statement. Today an interview. “We were great at loving each other. That was easy, but the relationship was very complicated. And it was always on-again, off-again, on-again off-again. And I went back close to nine times!”

John Mayer and Jessica Simpson Broke Up Nine Times During a Relationship: Rewind Romance

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 a 2010 interview with Playboy who quickly gained notoriety, Mayer was a little too revealing about his alcoholic relationship with Simpson, dashing all hope of them reuniting for the tenth time – thank goodness!

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“That girl, to me, is a drug,” he said. “And drugs are not good for you if you do a lot of them. Yes, that girl is like crack cocaine to me. Sexually, he was crazy. That’s all I’ll say. It was like napalm, sexual napalm. Did you ever say, ‘I want to give up my life and just fuck you? If you charged me $10,000 — you, I’d start selling all my stuff — just to keep you’.”

Understandably, the professionally squeamish Simpson was not thrilled to be described in such ludicrous terms (he later said, “I was floored and embarrassed that my grandmother was actually going to read that”) and snapped the singer-songwriter out of her life. “I deleted his number,” she wrote in her memoir. “It made it easy for me to walk away. I didn’t accept his apology. I deleted all his contact information from my phone. I was made with this man in a way I never thought possible. When he reached out to me, I changed my number and changed my email. Delete.” Boom – that napalm is on!

What They Said About Each Other

John Mayer and Jessica Simpson Broke Up Nine Times During a Relationship: Rewind Romance

John Mayer and Jessica Simpson in 2007 Kevin Mazur/WireImage

Thankfully, some of the couple’s other comments about their relationship were a little more granny friendly.

“He’d walk into a room and pick up his guitar, and you’d swoon,” 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 a conversation in February 2007 with Time Out New YorkMayer said he didn’t care if people thought they were an odd couple. “I’m having the time of my life,” he said. “So if the names don’t make sense to people, that’s so small to me.”

What They’re Saying Now

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

“He wanted to have me all or nothing,” Simpson wrote. “Time and time again, he told me he was obsessed with me, both sexually and emotionally. 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 find out what city I was in. It felt safe to be pleasant. I know John would never cheat on me, and that confidence was a new feeling for me.”

Simpson said Mayer’s highly sexualized comments about her felt like an unexpected betrayal from the man she thought she could rely on to seduce her. “He thought that was what I wanted to be called,” he wrote. “A woman and how they are in bed is not something that is ever talked about. It was stunning. He was the most loyal person on the planet, and when I read that he wasn’t, that was it for me.”

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

An older and wiser Simpson also knows now that his friends were never involved in the relationship. “He would dump me, then come back saying he found out he loved me after all,” she wrote. “I always saw him as him mercilessly taking me in from the cold. Every time John returned, I thought it was a continuation of a love story, while my friends saw a guy coming back for sex with some foolish girl.”

John Mayer and Jessica Simpson Broke Up Nine Times During a Relationship: Rewind Romance

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 clever for her – a source of sensitivity because she was ridiculed at the time as a “dumb blonde” which, of course, we’ve since learned . it couldn’t be further from the truth.

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

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Ever since Playboy interview, Mayer has sensibly kept a little quieter about his time with Simpson – but when Open Book published in 2020, Mayer’s close friend Andy Cohen have discussed the subject with him. “I’ve heard about it,” Mayer told the memoir. “I have heard some bits. But as Pee Wee Herman says in Pee Wee’s Big Adventure before the movie of his life is about to finally play out, he doesn’t watch the movie, and the reason he doesn’t watch the movie, he says, ‘I have nothing to watch, Dottie, I was living it.’ And I think that’s inherent here. “

But did Mayer ever officially apologize for the “sexual napalm” comments that destroyed Simpson? Well, almost. On stage in Nashville in 2010he was full of regret, explaining that “In an attempt to be clever, I completely forgot about the people I loved and the people who loved me” and said he had been in a “wormhole of selfishness, greed and arrogance”.

Later, in 2012, in an interview on NPR’s 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 open, but not honest, then you start free-associating junk. It doesn’t mean I can go back and scrub it out, but I understand it now.”

Key Relationship Takeaway Shops

John Mayer and Jessica Simpson Broke Up Nine Times During a Relationship: Rewind Romance

John Mayer and Jessica Simpson in 2007 Kevin Mazur/WireImage

This relationship was basically 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 he controlled me.”

Some people even believed that Simpson changed her image for Mayer, dying her trademark blonde hair to please him – but she maintains that this was not the case. “It didn’t make me a brunette,” she said Allure after their split. “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 now seemingly single, we doubt Simpson will be unblocking Mayer’s number anytime soon. Because ultimately, as she puts it, “That was Jess in her 20s.”

Now, as a 44-year-old mother of three, she knows better – and like Mayer? He hasn’t been so reckless since then, so maybe they both learned something.



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