Untangling Jessica Simpson’s Star-Studded Dating History

The two singers dated on and off for almost a year since summer of 2006, several months following her split from husband Nick Lachey. Simpson opened up about her relationship with Mayer in her 2020 memoir, Open Book. She said he repeatedly told her “he was obsessed with me, sexually and emotionally.”

Mayer had told Playboy in 2010 that Simpson was like “crack cocaine” to him, adding, “Sexually it was crazy. That’s all I’ll say. It was like napalm, sexual napalm.”

This did not sit well with his ex. “He thought that was what I wanted to be called,” Simpson wrote in her memoir. “I was floored and embarrassed that my grandmother was actually gonna read that.”

Two years later, Mayer expressed regret about his comments, telling NPR, “I had nothing to say. I was going through a time in my life where I didn’t really want to share what was going on, but I didn’t want to be boring.”

Simpson also wrote in her book that she was constantly worried she “wasn’t smart enough” for Mayer, adding, “My anxiety would spike and I would pour another drink. It was the start of me relying on alcohol to mask my nerves.”

On April 1, 2020, Mayer said on Watch What Happens Live With Andy Cohen that he had “heard some bits” about Simpson’s memoir, adding, “But as Pee Wee Herman says in Pee Wee’s Big Adventure before the movie of his life is about to play out at the end, he’s not watching the movie, and the reason he’s not watching the movie, he says, ‘I don’t have to watch it, Dottie, I lived it.’ And I think that’s prescient here.”

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