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    Jessica Simpson shades ex Tony Romo after reconnecting with bizarre interaction: ‘Glad we didn’t work out’

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

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

    The actress explained that she then received paperwork to sign the boat over to Romo. FilmMagic
    “And guess what he gave me as a thank you?” she said. REUTERS

    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.”

    “Plastic cups!” Simpson emphasized. US PGA TOUR
    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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