Jessica Simpson Is Counting Her Blessings For A Botched Romance 16 Years Ago

Jessica Simpson has no regrets about ending her past romance with ex-boyfriend Tony Romo!   

The sensational singer recently revealed she and her former beau awkwardly reconnected 16 years after their relationship ended. She declared the encounter made her count her blessings because she would have hated continuing a romance with the former NFL player.

Jessica Simpson's criticisms of her ex-boyfriend came months after she revealed that her second marriage was on the verge of collapse. She tied the knot to her estranged husband, Eric Johnson, in 2010, and announced in January 2025 that they had been living separately.

Simpson roasted her former boyfriend, Romo, during a performance at the 2025 Women Who Rock Benefit Concert in Pittsburgh. The concert took place earlier this month, with fan videos from the show capturing the moment the singer told the crowd about her awkward reunion with her ex.

Simpson revealed that Romo did not contact her directly; instead, he called her mom, informing her of his desire to sell a boat. She noted her mom was stunned by the sudden call, wondering why the former quarterback was telling her about his plans to sell the water vessel.

However, Romo explained he could not sell the boat because Simpson's name was on the title. The Daily Mail reported that the boat in question appeared to be the $100,000 speedboat she gifted her ex for his 28th birthday in 2009.

"So, then I get paperwork, and I have to sign over this boat for him to sell. And guess what he gave me as a thank you? Plastic cups!" Simpson told the crowd, adding, "I'm like, 'Wow, I'm glad we didn't work out.'"

Simpson and Romo began dating in 2007, reportedly leading to the singer becoming the target of NFL fans' criticism whenever the former Dallas Cowboys player performed poorly. He allegedly dumped her a day before her 29th birthday in 2009.

The "I Wanna Love You Forever" hitmaker later revealed that her relationship with Romo ended because her ex-boyfriend John Mayer still had a "hold" over her. She noted she was still in contact with the singer to Romo's displeasure.

Simpson began dating Mayer in 2006, with PageSix reporting that they seemed to have a very passionate relationship. Mayer once labeled Simpson his "sexual napalm" in an interview; however, she revealed in her 2020 memoir that their romance wasn't as pleasant as it seemed because of their on-and-off-again relationship.

Before Mayer, Simpson was romantically linked to Maroon 5 frontman Adam Levine during her first marriage to Nick Lachey. It was widely speculated that she cheated on her then-husband with the musician, but their affair was never confirmed.

Nonetheless, Simpson was caught leaving the Chateau Marmont in January 2006 after reportedly spending the night at Levine's house. The incident occurred after her separation from Lachey, but their alleged romance did not last.

Sources claimed Levine dumped Simpson via text in March 2006, the same year she finalized her divorce from Lachey. The singer and her first ex-husband met while she was on tour in 1999. They tied the knot in 2002 but ended their love story in 2005.

Last month, The Blast shared that Simpson wasn't closing her heart to love following her estrangement from her second husband. She revealed she was open to finding a new man but uninterested in joining dating platforms.

Instead, Simpson hoped her next beau could be someone her friends introduced her to. Sources added that her desire to move on came amid her amicable relationship with her estranged husband. They noted that she and Johnson managed to stay on friendly terms for the sake of their children.

The claims align with earlier reports from April, when Simpson, Johnson, and their three children were spotted spending time together in Carlsbad, California. Eyewitnesses noted they seemed distant but focused on keeping a good dynamic with their kids.

Following claims that Simpson was interested in finding love again, The Blast reported that she and Johnson were spotted taking a joint trip to Las Vegas.

They were seen boarding a commercial flight from Burbank, with the singer flashing a bright smile whenever someone noted it was good to see her and Johnson together.

Simpson's radiant appearance beside her estranged husband had many believing it was a sign of a possible reconciliation. She and the former NFL star even sat next to each other on the flight, with reports claiming they travelled to Las Vegas to support the entertainer's sister.

Ashley Simpson scored a residency gig at Sin City, an event that came months after her sibling revealed the dire state of her marriage. In January, the singer noted she and Johnson had been living separately. However, she claimed they would continue to prioritize their children amid the "painful situation."

Will Jessica Simpson reconcile with her estranged husband, or will he be the next ex to be roasted?