Jessica Simpson has revealed that she and John Mayer broke up and proceeded to get back together at least nine times over the course of their relationship. Their on-again-off-again romance was documented for years as they were seen out and about in Hollywood.

Simpson’s father being a preacher, Jessica began her career as a Christian singer, however, soon found that her body made it hard for record companies to want to sign her as some felt she did not look wholesome enough. Simpson topped the charts at the same time as Britney Spears and Christina Aguilera. In the summer of 2003, MTV aired Newlyweds: Nick and Jessica, which starred Nick Lachey and his then-wife Simpson and was one of the first reality tv shows. The two originally met when Lachey worked on one of Jessica’s music videos in 1999. The couple married in 2002, but in 2005 announced that they were divorcing.

Even though Mayer spoke out of turn in regards to Simpson in a Playboy interview, the two still seemed to try and keep their relationship intact according to E!.  In 2010 the singer spoke candidly as he forever linked Simpson to “sexual napalm.” The two have not been an official couple in over ten years, but fans have been reminded of their turbulent relationship thanks to Simpson’s new memoir, Open Book, which has catapulted their relationship back into the spotlight. The fashion designer decided to bare it all as she opened up about her diet pill addiction, getting sober, and sexual abuse that she suffered when she was a young girl.

The pop singer even wrote about the famous men of her life as Mayer was one of them. Simpson claimed in her book that he had told her multiple times that he was obsessed with her sexually and emotionally. Simpson had worried that he was too smart for her as she would constantly check her spelling and grammar before sending a text or email. The singer found Mayer to be very clever and that he treated a simple conversation like a “competition.” The blonde soon realized that her anxiety had started to become out of control and turned to alcohol. The singer did acknowledge that she and Mayer were great at loving one another, intimacy wise, but that the whole relationship was “complex” as they were always breaking up and then reuniting. Simpson revealed, “It was always on again, off again, on-again, off-again,” She recalled, “I went back close to nine times.”

While using alcohol to mask her nerves may have worked in the short term, ultimately the two crooners called it quits. Even though Simpson warned Lachey that she would be releasing a tell-all, she did not run it by Mayer. Simpson felt that at the end of the day, Mayer would be familiar with all the stories she spoke about as there was no love lost between them.

Next: Jessica Simpson Reveals Her Mom Suspected the Ongoing Sexual Abuse

Source: E!