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

Jessica Simpson and John Mayer had an on-again-off-again relationship that began in 2006. According to Simpson’s memoir, much of their courtship was filled with passion and excitement. Yet, at the same time, the pop star couldn’t help but feel a tremendous amount of anxiety whenever she was with him. Keep reading to find out why.

John Mayer and Jessica Simpson leave The Metropolitan Museum of Art's Costume Institute Gala May 7, 2007
John Mayer and Jessica Simpson leave The Metropolitan Museum of Art’s Costume Institute Gala May 7, 2007 | Evan Agostini/Getty Images

Jessica Simpson says the beginning of her relationship with John Mayer was amazing

After finalizing her divorce with the former 98 Degrees member, Nick Lachey, Simpson was finally on the market. Mayer began swooning over her the moment they met, continuously trying to win the pop star’s affections. Not long after, the two began a romantic relationship. In Simpson’s recently published memoir, she recalls how happy she was at the beginning of their romance.

John Mayer and Jessica Simpson at the Metropolitan Museum of Art in New York City
John Mayer and Jessica Simpson at the Metropolitan Museum of Art in New York City | James Devaney/WireImage

Unlike her marriage with Lachey where he spent most of his time avoiding her, Mayer was obsessed with Simspon. He seemed to crave her presence at all times… that is, until he didn’t. According to the pop star, Mayer broke up with her a total of nine times throughout the course of their on-again-off-again courtship. Yet as Simpson admits in her memoir, she was always willing to come back for more.

Jessica Simpson got so much anxiety around John Mayer that she had to start drinking

John Mayer and Jessica Simpson during Clive Davis' 2005 Pre-GRAMMY Awards Party
John Mayer and Jessica Simpson during Clive Davis’ 2005 Pre-GRAMMY Awards Party | L. Cohen/WireImage

RELATED: Was Nick Lachey Jealous of Jessica Simpson’s Fame?

As Simpson reveals in her new tell-all book, she had trouble feeling at ease around Mayer because he was constantly challenging her. He put an enormous amount of pressure on Simspon to be the best version of herself, which made her feel like she wasn’t already enough. Simpson also says that she felt like she wasn’t smart enough to be with Mayer, who deemed himself an intellectual.

“Where I felt insecure in the beginning was that I always felt that I was falling short of the potential he saw in me,” she writes. “I constantly worried that I wasn’t smart enough for him. He was so clever and treated conversations like a friendly competition that he had to win.”

As Simpson admits, the amount of pressure he put on her to be better made her start drinking to calm her nerves.

Jessica Simpson and John Mayer broke up after his infamous Playboy magazine interview

John Mayer and Jessica Simpson
John Mayer and Jessica Simpson | Brian Ach/WireImage

In 2010, Mayer gave a notoriously problematic interview with Playboy Magazine (Via Us Weekly.) In it, he blatantly discussed his sex life with his previous girlfriends. When talking about his relationship with Simpson, he said that she was like a drug to him and that even though drugs aren’t good for you, he can’t help but wanting more and more. (Note: This is the PG version of what he actually said.)

In response to his interview, Simpson was “floored and embarrassed that my grandmother was actually gonna read that.”

She continued, saying, “A woman and how they are in bed is not something that is ever talked about. It was shocking. 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. He made it easy for me to walk away.”