Jessica Simpson believes that parting ways with Tony Romo was ultimately a blessing in disguise. The 45-year-old "With You" singer took the stage at the 2025 Women Who Rock Benefit Concert at Stage AE in Pittsburgh on Friday, September 5, and during her performance, she regaled the audience with an amusing anecdote about her recent reconnection with Romo, 45, whom she dated from November 2007 to July 2009.
"A couple of weeks ago, my mom got a phone call," Simpson shared, as captured in a fan-recorded video from the concert. "And it was him calling my mom, saying, 'Well, Tina, I’m selling the boat.' And my mom’s like, 'Okay, and...?'"
"He’s like, 'Well, Jessica’s name is still on the title,'" she continued with a chuckle. "So, then I get this paperwork, and I have to sign over this boat so he can sell it."
"And guess what he gave me as a thank-you? Plastic cups!" Simpson exclaimed, drawing laughter from the crowd. "I’m like, 'Wow, I’m really glad we didn’t work out.'"
Back in 2009, the National Enquirer reported that the "A Public Affair" artist had gifted Romo a $100,000 speedboat. Simpson, who shares three children with her ex-husband Eric Johnson, had previously reflected on her relationship with Romo in her 2020 memoir Open Book, explaining that their breakup was triggered by her remaining in contact with her ex, John Mayer.
Earlier this month, PEOPLE caught up with Simpson (whose separation from Johnson was announced in January after a decade of marriage) at the 2025 MTV VMAs, where she playfully revealed her picks for this year’s Sexiest Man Alive title.
"I mean, there are a lot of people who are sexy," she said coyly, a twinkle in her eye. "I’m single, so everybody’s sexy right now!"
After listing Charlie Hunnam, James Franco, and Jamie Dornan as her top contenders, Simpson added with a grin, "There are a lot of hotties out there... a lot of cute guys."
Simpson’s latest EP, Nashville Canyon, Pt. 2, dropped on September 5 and features tracks like "Savage" and "Your Apology."
