Jessica Simpson revealed she recently reconnected with ex-boyfriend Tony Romo over an unexpected legal matter involving a boat she bought him during their relationship.
The singer, 45, shared the story during her performance at the 2025 Women Who Rock Benefit Concert at Stage AE in Pittsburgh on Friday. Simpson and the former Dallas Cowboys quarterback dated from November 2007 to July 2009.
“A couple weeks ago my mom got a phone call. And he’s calling my mom, saying, ‘Well, Tina, I’m selling the boat.’ And my mom’s like, ‘Okay, and?'”
Simpson explained the situation to the crowd, according to a fan video from the show.
“He’s like ‘Well, Jessica’s name is still on the title.’ So, then I get paperwork, and I have to sign over this boat for him to sell.”
The boat in question was a $100,000 speedboat Simpson purchased for Romo as a gift in 2009, according to reports from the National Enquirer.
But Simpson wasn’t impressed with Romo’s gesture of appreciation.
“And guess what he gave me as a thank you? Plastic cups. I’m like, ‘Wow, I’m glad we didn’t work out.'”
Simpson shares three children with ex-husband Eric Johnson. The couple announced their separation in January after 10 years of marriage.
In her 2020 memoir Open Book, Simpson reflected on her relationship with Romo. She explained their breakup happened because she stayed in contact with ex John Mayer during their relationship.
Simpson Embraces Single Life
At the 2025 MTV VMAs earlier this month, Simpson spoke with PEOPLE about her current dating outlook. When asked about this year’s Sexiest Man Alive title, she had a playful response.
“I mean, there are a lot of people who are sexy. I’m single, so everybody’s sexy right now!”
She listed Charlie Hunnam, James Franco and Jamie Dornan as top picks.
“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 September 5. The collection features songs including “Savage” and “Your Apology.”
