Jessica Simpson Sends Subtle Shade to Tony Romo After Awkward Reconnection: ‘Glad We Didn’t Work Out’.qn

Jessica Simpson savagely slammed ex-boyfriend Tony Romo after they were forced to reconnect — and close financial ties — over a boat.

“He’s calling my mom, saying, ‘Well, Tina, I’m selling the boat.’ And my mom’s like, ‘OK, and?’” the “Irresistible” songstress told the crowd at the 2025 Women Who Rock Benefit Concert in Pittsburgh, per a fan video.

“He’s like ‘Well, Jessica’s name is still on the title,’” she added of Romo, who has been in possession of the vessel since their split. “So, then I get paperwork, and I have to sign over this boat for him to sell.”

Jessica Simpson at the 2025 Women Who Rock Benefit Concert in Pittsburgh on Friday, per a fan video.

Jessica Simpson called out ex-boyfriend Tony Romo while performing at the 2025 Women Who Rock Benefit Concert in Pittsburgh, per a fan video. @jordycray/TikTok

Jessica Simpson and Tony Romo pose together.

The hitmaker told the crowd that the former athlete called her mom to inform her that he was selling a boat in Simpson’s name. WireImage

“And guess what he gave me as a thank you?” Simpson, 40, teased. “Plastic cups!”

“I’m like, ‘Wow, I’m glad we didn’t work out,’” she continued, as the audience cheered.

The hitmaker was seemingly talking about the reported $100,000 speedboat she gifted to the retired  Dallas Cowboys for his 28th birthday in 2009, according to the National Enquirer.

Reps for Romo, 45, weren’t immediately available to Page Six for comment.

Tony Romo and singer Jessica Simpson perform onstage at the 2008 ESPY Awards held at NOKIA Theatre L.A. LIVE on July 16, 2008 in Los Angeles, Calif

“He’s calling my mom, saying, ‘Well, Tina, I’m selling the boat.’ And my mom’s like, ‘OK, and?’” she shared. WireImage

Tony Romo gets a kiss from girlfriend Jessica Simpson in the second half of the Mavericks' NBA game against the Los Angeles Lakers at the American Airlines Center in Dallas, Texas in 2008.

“He’s like ‘Well, Jessica’s name is still on the title,’” Simpson added. Tribune News Service via Getty Images

Romo and Simpson started dating in September 2007.

At the time, the “Dukes of Hazzard” star took a lot of heat for their romance, with Cowboys fans blaming her for Romo’s poor performance on the field.

The exes dated for two years before the NFL alum allegedly broke up with the “Newlyweds” alum one day before her 29th birthday in 2009.

Jessica Simpson (L) and quarterback Tony Romo sighting on April 11, 2009 in Hollywood, Calif

The actress explained that she then received paperwork to sign the boat over to Romo. FilmMagic

Tony Romo (L) and Jessica Simpson (R) watch the NBA action between the Dallas Mavericks and LA Lakers in Dallas, Texas March 18, 2008.

“And guess what he gave me as a thank you?” she said. REUTERS

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Simpson later got candid about her split from Romo, admitting in her 2020 memoir, “Open Book,” that her former romance with musician John Mayer led to their estrangement.

The “Fashion Star” alum claimed that she would still talk to her ex, saying the “Free Fallin’” crooner had a “hold” on her.

“If John texted or emailed, I would hold up my phone and tell Tony immediately,” she wrote. “He knew the hold John had over me, and it was like telling your sponsor when you’re triggered.”

Jessica Simpson poses with Tiger Woods and Tony Romo.

“Plastic cups!” Simpson emphasized. US PGA TOUR

Tony Romo and Jessica Simpson at a golf match.

The exes dated from 2007 to 2009. REUTERS

Simpson and Mayer had an on-again, off-again romance from 2006 to 2010.

The pop star is currently divorcing her estranged husband, Eric Johnson, with whom she wed in July 2014 and welcomed three kids: Maxwell, Ace and Birdie.

She was also previously married to Nick Lachey from 2002 to 2006.

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