Check Out Jessica Simpson's Dating History!

Nick Lachey: Probably Simpson’s most famous partner and one of her true loves. They have both spoken about how happy they truly felt with each other, but sadly could not make it work. Lachey told ‘Rolling Stone’: “It breaks my heart that I couldn’t make Jessica happy. I wanted to be everything to my wife […]”, while Simpson wrote in her book, “I was 22, and I had just pledged my life and destiny of this man. And I don’t regret it. Nick was meant to be my husband. No one else was supposed to have my virginity.”

Nick Lachey: Probably Simpson’s most famous partner and one of her true loves. They have both spoken about how happy they truly felt with each other, but sadly could not make it work. Lachey told ‘Rolling Stone’: “It breaks my heart that I couldn’t make Jessica happy. I wanted to be everything to my wife […]”, while Simpson wrote in her book, “I was 22, and I had just pledged my life and destiny of this man. And I don’t regret it. Nick was meant to be my husband. No one else was supposed to have my virginity.”

Adam Levine: Although never confirmed, it is rumored that Simpson was unfaithful with Lachey in 2004, when she had some sort of relationship with Levine. Acoording to ‘Us weekly’ CaCee Cobb picked up Simpson after Levine dumped her via text message.

Adam Levine: Although never confirmed, it is rumored that Simpson was unfaithful with Lachey in 2004, when she had some sort of relationship with Levine. Acoording to ‘Us weekly’ CaCee Cobb picked up Simpson after Levine dumped her via text message.

John Mayer: After her divorce from Lachey in 2005 she began dating the “Your Body Is a Wonderland” singer, but their relationship was far from a healthy one. ‘Page Six’ reports they broke up nine times, and Simpson wrote in her book, “Again and again, he told me that he was obsessed with me, sexually and emotionally,” until he lost interest, “When he tapped me dry, he looked at me like I was withholding something from him.”

John Mayer: After her divorce from Lachey in 2005 she began dating the “Your Body Is a Wonderland” singer, but their relationship was far from a healthy one. ‘Page Six’ reports they broke up nine times, and Simpson wrote in her book, “Again and again, he told me that he was obsessed with me, sexually and emotionally,” until he lost interest, “When he tapped me dry, he looked at me like I was withholding something from him.”

Tony Romo: The singer took a break from dating singers and tried sports stars intead, in the form of the NFL pro Dallas Cowboys quarterback. However, after two years of relationship they broke up, partly because Mayer still had a “hold” over her, according to Simpson but the pair would also fight often, acording to friends of Romo, “They go from one fight right into another, without a second break.”

Tony Romo: The singer took a break from dating singers and tried sports stars intead, in the form of the NFL pro Dallas Cowboys quarterback. However, after two years of relationship they broke up, partly because Mayer still had a “hold” over her, according to Simpson but the pair would also fight often, acording to friends of Romo, “They go from one fight right into another, without a second break.”

Eric Johnson: Another former NFL player, Johnson was finilizing his divorce with his former wife, Keri D’Angelo, when he began dating Simpson in May 2010. They got engaged months before he finally got divorced in october 2010. Simpson and Johnson welcomed their daughter Maxwell in 2012, son Ace in 2013, and daughter Birdie in 2019.

Eric Johnson: Another former NFL player, Johnson was finilizing his divorce with his former wife, Keri D’Angelo, when he began dating Simpson in May 2010. They got engaged months before he finally got divorced in october 2010. Simpson and Johnson welcomed their daughter Maxwell in 2012, son Ace in 2013, and daughter Birdie in 2019.