American singer, Jessica Simpson is one of the most loved artists, who began her singing career at the age of 17. At 19, her debut album sold two million copies in the United States. Beyond her singing career, Jessica made her acting debut in The Dukes of Hazzard in 2005. Apart from her professional life, Jessica often hit the headlines for her personal life.

The singer and actress, who announced her split from NFL player, Eric Johnson after ten years of marriage, recently grabbed headlines when she stated she is ready to date again. Although it has been two years since Jessica and Eric parted ways, the duo officially announced their split in January 2025. In a recent interaction, when Jessica was asked whether she is interested in dating, the stunning singer said she was into the idea of being set up on a date.

Jessica Simpson is an open book when it comes to dating. The actress has been open about her relationship and never hidden anything from her fans. Her failed marriages, broken relationships and casual flings. Let us take a look at the relationship timeline of the Take My Breath Away singer.

Jessica Simpson’s marriage to Nick Lachey

Nick Lachey was the first celebrity who made Jessica’s heart flutter. She met him on tour in 1999, and the duo fell in love. The couple got married in 2002 and also starred in their own reality show, Newlyweds: Nick and Jessica. However, destiny had other plans and the couple called it quits in 2005, with their divorce being officially finalised in 2006.

Jessica Simpson had an ‘emotional affair’ with Johnny Knoxville

While Jessica had a split with Nick Lachey and their divorce wasn’t finalised, the actress had an ‘emotional affair’ with her Dukes of Hazzard co-star, Johnny Knoxville. The two never addressed their dating rumours since both were married, but Jessica accepted her ‘emotional affair’ with him, stating that the stuntman had embraced her vulnerabilities and believed in her.

Jessica Simpson allegedly cheated on her husband, Nick Lachey, with ‘Maroon 5’ singer, Adam Levine

Many reports claim that Jessica fell in love with Maroon 5 frontman, Adam Levine while she was still married to Nick Lachey. The reports claimed that Jessica met Adam in 2004 and cheated on her husband with Adam. In January 2006, the gorgeous singer was seen leaving Adam’s house. In March 2006, Jessica was reportedly dumped by Adam via text message.

Jessica Simpson’s on-and-off relationship with John Mayer

Out of the many relationships Jessica had, the most controversial one was with singer, John Mayer. Right after her divorce from Nick Lachey was finalised in 2006, Jessica got into a passionate relationship with John, which many termed as ‘toxic romance’. From breaking up multiple times to Mayer calling Simpson ‘S**ual napalm’, the two always made it to the headlines. After nine breakups in a year, the two called it quits.

Jessica Simpson dated NFL pro, Tony Romo

After breaking up with John Mayer, Jessica Simpson went on to have an affair with NFL pro, Tony Romo in 2007. During their dating spree, Jessica was blamed for Tony’s poor performance. However, their affair was short-lived as Jessica was not over John and would continue to chat with him, which irked Tony. However, in 2009, the NFL player broke up with Jessica.

Jessica Simpson’s ten-year-long marriage and split from American footballer, Eric Maxwell Johnson

After a series of heartbreaks, Jessica Simpson finally found the love of her life in former American football star, Eric Maxwell Johnson in 2010. After dating for four years, the duo tied the knot in 2014 and soon welcomed three children, Maxwell, Ace, and Birdie Mae.

However, there were rumours pertaining to their fallout, but it was in January 2025, when the couple officially confirmed their separation. Talking to People about her separation, the singer said:

“Eric and I have been living separately navigating a painful situation in our marriage. Our children come first, and we are focusing on what is best for them. We are grateful for all of the love and support that has been coming our way, and appreciate privacy right now as we work through this as a family.”

Did you know about these leading men in Jessica Simpson’s life? Let us know.