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Jessica Simpson Got Back Together With John Mayer 9 Times Before Deleting His Number

The two musicians had a tumultuous on-again, off-again relationship in the late '00s.

Despite incredibly different musical styles, singers John Mayer and Jessica Simpson were drawn together in a fiery on-again, off-again relationship for nearly four years in the late 2000s. In her 2020 memoir Open Book, Simpson gave an unflinching look at what life inside the relationship was like, including the whopping nine times they split before she finally decided she wasn't going back. Read on to learn why it was so hard for her to walk away from the obsessive relationship and how Mayer's infamous 2010 Playboy interview finally convinced her to delete his number.

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They met when Simpson was still married.

Jessica Simpson and Nick Lachey in 2004
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Simpson was still married to first husband, 98 Degrees member Nick Lachey, when she met Mayer at a 2005 Grammys party thrown by Clive Davis. According to People, Mayer complimented Simpson on her song "With You," and two began writing letters to each other. When Simpson and Lachey divorced later that year, she started dating other men. But when the "Daughters" singer told her "he wanted to have all of [her] or nothing," the two went secretly exclusive before he confirmed the relationship—in Japanese—in a 2007 interview with Ryan Seacrest.

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Mayer told Simpson he was "obsessed" with her.

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

Simpson said in her book that her relationship with Mayer was characterized by a mix of emotional distance and obsession. "He'd walk into a room and pick up his guitar and you'd swoon," she wrote, according to People. "I didn't really know the man behind the guitar. And that was my mission. Again and again, he told me he was obsessed with me, sexually and emotionally."

As quote by InStyle, the pop star explained that Mayer's attachment to her initially made her feel safe and gave her a boost of confidence, because it was so different from her relationship with Lachey.

"I would get up to go to the bathroom, and John would ask, 'Where are you going?'," Simpson wrote. "While I was married, my ex-husband couldn't be bothered to figure out what city I was in."

What made her feel less secure though is that Mayer constantly tried to one-up her intellectually.

"He was so clever and treated conversation like a friendly competition that he had to win," she wrote, per People.

Soon she was so "constantly worried" that she wasn't smart enough for the "Body is a Wonderland" singer that she would have a friend proofread text messages before she sent them and began using alcohol to quell the anxiety.

They broke up nine times.

Jessica Simpson and John Mayer leaving the Met Gala in 2007
Evan Agostini/Getty Images

Mayer and Simpson's relationship came to an end for the first time in May 2007, according to InStyle, but they ended up getting back together and breaking up another eight times.

"He'd dump me, then come back saying he had discovered he loved me after all," Simpson wrote, per Yahoo!. "I always saw it 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."

The two stayed in contact even when seeing other people, including when Simpson dated Tony Romo, who she wrote broke up with her after seeing a text from Mayer. She came to regret the four years they spent in this cycle.

"He loved me in the way that he could and I loved that love for a very long time," she told People. "Too long. And I went back and forth with it for a long time. But it did control me."

She deleted his number after a shocking Playboy interview.

John Mayer in 2010
Andrew H. Walker/FilmMagic

The straw that broke the camel's back came in the form of Mayer's 2010 interview with Playboy, which took place during an "off" period for him and Simpson, when he was involved with Jennifer Aniston. Among other surprising quotes, Mayer went deep on his obsession with Simpson: "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." He also spoke candidly of their sex life, saying, "Sexually, it was crazy. That's all I'll say. It was like napalm, sexual napalm."

Simpson was mortified. "I was floored and embarrassed that my grandmother was actually gonna read that," she told People. But the brazen comments ended up being what she needed to finally go scorched earth on their on-again, off-again relationship.

"I didn't accept his apology," she wrote, per Yahoo!. "I deleted all his contact information from my phone. I was done with this man in a way I never thought was possible. When he reached out to me, I changed my number and changed my email. Delete."

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She later said she felt "manipulated."

Jessica Simpson and Eric Johnson in 2023
Ella Hovsepian/Getty Images

Now married to former NFL player Eric Johnson, with whom she shares three children, Simpson said that a conversation with her therapist opened her eyes to the idea that what Mayer felt for her was not love, but obsession, according to Yahoo!. She also reserved the right to discuss the ugly parts of her former relationship openly, despite Mayer's public apology for his interview comments.

"I definitely don't feel that I am owed a public apology," she said on Tamron Hall's talk show (as quoted by E! News) while promoting her memoir. "You can't take it back. I'm a very forgiving person, but I'm also honest. So, in the memoir, if I'm gonna talk about stuff that caused me pain, I'm going to be honest about it. And that was a time in my life that I was very manipulated and very also in love, or seemingly."

Andrew Miller
Andrew Miller is a pop culture writer living in New York. Read more
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