Jessica Simpson is in her rock era, and she's exposing exes in between hits. The newly single songstress performed at the 2025 Women Who Rock Benefit Concert in Pittsburgh on September 5, and she revealed that her ex, Tony Romo, recently called her mom trying to get a hold of her.
© GettySimpson and Romo dated from 2007 to 2009 and were tabloid sensations. Both at the top of their careers, things were so serious that she even gifted him a $100k luxury speedboard for his 28th birthday in 2008. Nearly two decades later, it seems like the retired quarterback is selling the boat.
The 45-year-old "Sweet Kisses" singer told the Pittsburgh audience that Romo reached out to her mom on the phone a couple of weeks prior, which would have been sometime in August. "Well, Tina, I’m selling the boat.’ And my mom’s like, ‘OK, and?’” Jessica told the crowd in a video posted to TikTok.
Romo reminded her mother that Jessica’s name was still on the title, forcing the singer to deal with the paperwork years after their split. “So, then I get paperwork, and I have to sign over this boat for him to sell,” she explained.
© GettySimpson teased, “And guess what he gave me as a thank you?” “Plastic cups!” she laughed. The full circle moment had Simpson thankful. “I’m like, ‘Wow, I’m glad we didn’t work out,'" she quipped.
Their relationship was a rollercoaster on and off the field. At the time, Cowboys fans blamed Simpson for Romo’s bad games and labeled her a “jinx.”
© GettyIn her 2020 memoir Open Book, she said he broke things off the night before her 29th birthday in July 2009. The reason why? John Mayer texted her. “Tony confronted me with it immediately," she said, explaining that although she never cheated, he still broke up with her as soon as he saw the message.
Simpson then found love with another NFL player, Eric Johnson, and they said I do in 2014, and they share three children: Maxwell, 13, Ace, 12, and Birdie, 6. The two announced their separation in January 2025.
© GettyMore than 15 years after Romo, and just months after her most recent heartbreak, Simpson is proving that she's going to wear her head high and eventually get the last laugh.
