Skip to main content

Jessica Simpson and John Mayer shared a tumultuous relationship for several years. According to Simpson, Mayer broke up with her a total of nine times before she finally decided she had enough. But while they were together, the pop star began seeing a therapist, who told her point-blank: “He never loved you.”

Jessica Simpson and John Mayer
Jessica Simpson and John Mayer | LRRB and Co./WireImage

When did Jessica Simpson and John Mayer date?

Simpson and Mayer started their love affair in 2006. According to Simpson, the beginning of their relationship was magical. She was just getting over a divorce from Nick Lachey, who didn’t give her the attention she so desperately craved. Yet with Mayer, it was the exact opposite. He was obsessed with her.

John Mayer and Jessica Simpson
John Mayer and Jessica Simpson | Larry Marano/Getty Images

“Again and again, he told me he was obsessed with me, sexually and emotionally,” she writes. “The connection was so strong that he made me feel seductive, and he spoke about my body in a way that made me feel powerful. His focus on me was the opposite of my marriage,” says Simpson. “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 so desired.”

Yet despite how great things were at the beginning of their romance, things started to get rocky the closer they became. Soon, Mayer began to play hot and cold with the pop star. He would break up with her over what seemed like every little thing, and it got to the point where Simpson felt extremely anxious around her boyfriend. She felt like she had to be perfect for him, and it got exhausting over time.

Jessica Simpson and John Mayer
Jessica Simpson and John Mayer | James Devaney/WireImage

“I was so afraid of disappointing him that I couldn’t even text him without having someone check my grammar and spelling,” she writes. “This drove my mother nuts. ‘That is a terrible relationship,’ she said, ‘if you have to be scared you misspelled something.'”

Jessica Simpson’s therapist said John Mayer never loved her

John Mayer in concert at Royal Albert Hall September 17, 2007
John Mayer in concert at Royal Albert Hall September 17, 2007 | Chiaki Nozu/FilmMagic

As much as Simpson adored the guitar-god, Mayer’s feelings weren’t mutual. He wasn’t in love with her, but “obsessed.”

When Simpson told her therapist about their relationship, her therapist said, “That’s not love. You know that, right? I mean, he never loved you.”

“What do you mean, he never loved me?” Simpson asked.

“He was obsessed with you,” she said. “Love and obsession are so different. One is healthy. One is not.”

Why did Jessica Simpson and John Mayer break up?

John Mayer and Jessica Simpson
John Mayer and Jessica Simpson | Lester Cohen/WireImage for J Records
Related

Jessica Simpson Says Her Relationship With John Mayer Gave Her ‘Anxiety’

Simpson and Mayer officially broke things off after the singer’s infamous Playboy Magazine interview from 2010. In the interview, Mayer detailed their sex life to the public. This left her feeling humiliated.

“I didn’t accept his apology,” Simpson said of the interview. “I deleted all his contact information from my phone. When he reached out to me, I changed my number and changed my email. Delete.”