Jessica Simpson and Dallas Cowboys Quarterback Tony Romo backstage after Jessica finished her first live performance in 3 years
Jessica Simpson and Tony Romo in July 2008.
Jessica Simpson thinks splitting from Tony Romo was for the best.
The "With You" singer, 45, performed at the 2025 Women Who Rock Benefit Concert at Stage AE in Pittsburgh on Friday, Sept. 5 and spoke to the crowd mid-show about recently reconnecting with Romo, 45, after they dated from November 2007 to July 2009.
"A couple weeks ago my mom got a phone call," said Simpson, according to a fan video from the show. "And he's calling my mom, saying, ‘Well, Tina, I’m selling the boat.’ And my mom’s like, ‘Okay, and?’”
Tony Romo attends the 2022 Paramount Upfront at 666 Madison Avenue on May 18, 2022 in New York City.
Tony Romo attends the 2022 Paramount Upfront at 666 Madison Avenue on May 18, 2022 in New York City.
"He’s like ‘Well, Jessica’s name is still on the title,’" she added. "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," said Simpson. "I’m like, ‘Wow, I’m glad we didn’t work out.'"
In 2009, the National Enquirer reported the "A Public Affair" artist purchased a $100,000 speedboat for Romo as a gift.
Jessica Simpson attends the 2025 MTV Video Music Awards at UBS Arena on September 07, 2025 in Elmont, New York.
Jessica Simpson attends the 2025 MTV Video Music Awards at UBS Arena on September 07, 2025 in Elmont, New York.
Simpson, who shares three kids with ex-husband Eric Johnson, reflected on dating Romo in her 2020 memoir Open Book and explained their split was caused by her remaining in contact with ex John Mayer.
PEOPLE caught up with Simpson (whose separation from Johnson was announced in January after 10 years of marriage) at the 2025 MTV VMAs earlier this month, and she revealed who she wants to win this year’s Sexiest Man Alive title.
"I mean, there are a lot of people who are sexy," she said coyly. "I'm single, so everybody's sexy right now!"
After listing Charlie Hunnam, James Franco and Jamie Dornan as her top picks, Simpson added, "There are a lot of hotties… There are a lot of cute guys out there."
Simpson's latest EP, Nashville Canyon, Pt. 2, was released on Sept. 5 and features songs including "Savage" and "Your Apology."