Jessica Simpson Says Tony Romo Dumped Her Over John Mayer

Jessica Simpson had a long list of relationships before marrying former NFL player Eric Johnson and welcoming their three children. The 90s blonde bombshell was married to Nick Lachey, prompting their reality show "Newlyweds." Years later, while hosting "Love Is Blind," Lachey seemingly shaded Simpson and their union, claiming that marriage is better the second time. Several of Simpson's other exes have come forward to speak about their experience with the "Employee of the Month" star, and it seems like everyone could use a lesson in the art of don't kiss and tell.

But Simpson also opened up about several of her past relationships in her 2020 memoir, "Open Book." She wrote about her relationship with Johnny Knoxville, whom she worked with on "Dukes of Hazzard," and said that they had an emotional affair on-set while she was married to Lachey and he was married to Melanie Lynn Clapp. "I could share my deepest authentic thoughts with him, and he didn't roll his eyes at me. He actually liked that I was smart and embraced my vulnerabilities," Simpson wrote of Knoxville. "He believed in me and made me feel I could do anything." 

While this garnered a lot of headlines, Simpson's on-again, off-again relationship with John Mayer was also a huge part of her story and it's the reason her relationship with Tony Romo fell apart.

John Mayer and Jessica Simpson dated from 2006 to 2007, but it wasn't continuous dating. Simpson told Hoda Kotb in a "Today" interview how complicated things were with Mayer. "We were great at intimacy," she began. "We were great at loving each other. That was easy, but the relationship was very complex, and it was always on-again, off-again, on-again, off-again. And I went back close to nine times."

In the tumult of Mayer, Simpson met the Dallas Cowboys quarterback Tony Romo and they began dating in November 2007. "The fact that this guy, on our first date, in the first 10 minutes of dinner, wanted to lean over the table and say, 'This is my girl and I want to kiss her' — our first kiss in front of everybody — was awesome," she said of their first date. However, in May 2008, rumors broke that Romo and Simpson were facing some relationship conflict, as Simpson became upset when Mayer started dating Jennifer Aniston.

Mayer's presence in their relationship became a significant source of conflict. They made  a deal that, if Mayer reached out to her, she'd tell Romo. "If John texted or emailed, I would hold up my phone and tell Tony immediately," Simpson wrote in her memoir, "Open Book." "He knew the hold John had over me, and it was like telling your sponsor when you're triggered." Despite her best efforts at complete disclosure, Mayer essentially destroyed her connection to Romo.

Even when Jessica Simpson was dating Tony Romo, John Mayer continually tried to stay in her life by fostering relationships with her father, her sister, Ashlee Simpson, and her sister's then-husband, Pete Wentz. Jessica's father invited Mayer over to their home in Los Angeles while she was still with Romo and this was where the serious problems started. "By a fire in the backyard, [Mayer] 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," Jessica wrote in her memoir. "But I didn't tell Tony. I broke my own rule of full disclosure about any contact, even accidental, with John."

Later, Romo saw an email from Mayer to Jessica in 2009 and that was the last straw. "I hadn't cheated on Tony at all, but I could not lie and say I hadn't even seen him," Jessica said. "And within that second, he broke up with me right there. Two years, gone with an email."

Following this, Mayer gave his infamous 2010 Playboy interview, where he gave a completely uncensored take on his relationship with Jessica. "Sexually it was crazy," he said. "That's all I'll say. It was like napalm, sexual napalm." Years later, Jessica admitted to The New York Times that Mayer was obsessed with her, not in love with her, and this discovery was brutal. "Ooh, that broke me in half!" she said.