According to Jessica Simpson, she went back to John Mayer over and over again after breaking up with him. She even admitted in her new memoir Open Book that she was basically addicted to him. Their relationship is a recurring motif in her autobiography, and Mayer has spoken in similar terms.
Jessica Simpson has been in a lot of high-profile romances. She was married to Nick Lachey for four years in the early 00s and has been married to former 49er tight end Eric Johnson for the last five. She’s also been in relationships with Smashing Pumpkins’ frontman Billy Corgan, Maroon Five singer Adam Levine, comedian Dane Cook, and actor and stuntman Johnny Knoxville, among others.
Mayer has a similarly diverse relationship history. Jennifer Love Hewitt, Jennifer Aniston, Taylor Swift, Katy Perry, and even Kim Kardashian have all dated the Dead & Co. guitar player over the last couple of decades. He’s even been rumored to be dating Halsey, though Gossip Cop debunked that claim.
Mayer and Simpson’s relationship began in 2006 after her marriage to Lachey ended was the toughest to deal with. They would date off and on for the next four years, with a long break in between. By her own account, Simpson went back to Mayer nine times.
John Mayer and Jessica Simpson’s relationship wasn’t simple
From 2007 to 2009, Simpson famously dated Dallas Cowboys quarterback Tony Romo. The singer was a near-constant presence at his games, but behind the scenes, there was a problem: Mayer was still calling and texting. Simpson writes in Open Book that she always told Romo when Mayer texted, saying, “It was like telling your sponsor when you’re triggered.” Still, one night in 2009, Mayer ended up at her house and declared his love for her during a get-together in her backyard. Simpson writes, “I told him I would always love him, but I was with Tony, but I didn’t tell Tony.”
It was an accident, she didn’t mean to hide the meeting from him but soon after, Romo questioned Simpson about an email from Mayer, and she told him the story. Romo broke up on the spot and Simpson went back to Mayer. They lasted another few months until a now-infamous Playboy interview with Mayer in 2010 was published. Mayer compared her to crack cocaine and described her as “sexual napalm.” It seems Simpson wasn’t the only one addicted to their chemistry.
Simpson broke it off with him for good after the interview. In her book, she writes that she changed her email and her phone number and never looked back — at least until she wrote this book. In it, she’s able to come to grips with the hold Mayer had on her. She told Hota Kolb on Today, “We were great at intimacy, We were great at loving each other. That was easy, but the relationship was very complex.” Now, happily married for almost six years, it seems she has conquered her addiction for good.