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Jessica Simpson Reveals The Comment John Mayer Made That Ended Their Tumultuous Relationship

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Jessica Simpson, John Mayer

John Mayer and Jessica Simpson’s toxic relationship is being analyzed once again after another of Mayer’s exes appeared to take aim at him in recent weeks.

Taylor Swift, who briefly dated Mayer in 2009, once again probed their large age gap in “Could’ve, Would’ve, Should’ve,” a track from her latest album “Midnights.”

Now, fans are delving into Mayer's alleged history of toxic behavior in relationships and what Simpson has revealed about dating him.

What happened between Jessica Simpson and John Mayer?

Mayer and Simpson dated on and off between 2006 and 2010 but the drama surrounding their split dragged on for much longer.

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Simpson has since called out Mayer, in her 2020 memoir “Open Book” and revealed how he allegedly mistreated her during their relationship.

Simpson says dating Mayer made her insecure.

A year after her divorce from ex-husband Nick Lachey in 2005, Simpson started dating Mayer. 

Initially, Simpson revealed in her memoir that she “fell in love with his intensity,” later adding, “again and again, he told me he was obsessed with me, sexually and emotionally”. 

That passion and intensity quickly spiraled into insecurity, Simpson explained in a 2020 interview that she, “Constantly worried that I wasn’t smart enough for him.”

“We were great at loving each other. That was easy, but the relationship was very complex… I went back close to 9 times.” 

Simpson says she turned to alcohol and drug while dating Mayer.

In her memoir, Simpson said, “[Mayer] was so clever and treated conversation like a friendly competition he had to win.”

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She also revealed her rocky relationship with Mayer sparked her spiral into drinking and drug addictions – the anxiety and insecurity from their relationship led Simpson to start “relying on alcohol to mask [her] nerves.”

Simpson claimed Mayer broke up her relationship with Tony Romo.

After months of “on and off” dating, Simpson and Mayer broke things off once again, and Simpson started a new relationship with NFL star, Tony Romo in 2007.

According to her book, Mayer repeatedly tried to make contact with Simpson over email and text during her new relationship. 

According to Page Six, Simpson had a “full disclosure” agreement with Romo, where “If John texted or emailed, I would hold up my phone and tell Tony immediately”. 

Even after Mayer and Simpson broke things off, Simpson revealed that Mayer kept close contact with many of her family members during her relationship with Romo. 

At a family event where Mayer was present, he allegedly confessed his continued love for her.

Simpson recalls, “he stood and told all of us that he loved me and that we could all trust him to be a good man. I told him I would always love him, but I was with Tony. But I didn't tell Tony. I broke my own rule of full disclosure about my contact, even accidental, with John”. 

Weeks after Mayer’s confession, Romo confronted Simpson about new messages from Mayer and broke things off due to cheating suspicions.

Mayer’s attachment to Simpson and his “addictive” relationship ultimately ended Simpson and Romo’s relationship, even under false cheating suspicisons. 

She got back with Mayer soon after this split.

Mayer’s interview with ‘Playboy’ ended their relationship for good.

The couple finally split in 2010, following uproar from Mayer’s 2010 Playboy interview where he called his relationship with Simpson “an addiction…sexual napalm”. 

Her memoir goes into great detail about the hurt and “embarrassment” after reading the comments Mayer had made about her and their relationship.

“He was the most loyal person on the planet and when I read that he wasn’t, that was it for me. I erased his number,” she wrote.

Alongside her recall of their relationship, she does into further detail on her addictions and recovery. 

In 2020, Mayer told Andy Cohen in an interview that he hasn’t read the memoir, and “likely won’t.” 

Simpson has now been married to her current husband, football player Eric Johnson, since 2014, and the two share three children together.

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Zayda Slabbekoorn is a news and entertainment writer at YourTango. They cover topics ranging from pop culture analysis to human interest stories. They are currently based in East Lansing, MI. Catch up with them on their Instagram or TikTok.

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