Jessica Simpson publicly referenced her former relationship with NFL quarterback Tony Romo onstage at the 2025 Women Who Rock Benefit Concert in Pittsburgh, saying the two were forced to reconnect after Romo sought to sell a boat that still had Simpson’s name on the title.
Simpson, 40, told the crowd — according to a fan video posted on TikTok — that Romo contacted her mother to announce his intention to sell the vessel and that she subsequently received paperwork requiring her signature to transfer the title. "And guess what he gave me as a thank you? Plastic cups!" she said, adding, "I’m like, ‘Wow, I’m glad we didn’t work out.'" Reps for Romo, 45, were not immediately available for comment to Page Six.
The exchange appeared to refer to a speedboat Simpson reportedly gave Romo while they were dating; the National Enquirer previously reported the vessel’s value at about $100,000. Simpson and Romo dated from 2007 to 2009, a period that drew intense tabloid and fan scrutiny. The couple broke up in 2009.
In her 2020 memoir Open Book, Simpson wrote that her relationship with musician John Mayer contributed to a rift with Romo, saying Mayer had "a hold" on her and that she often alerted Romo when Mayer contacted her. The onstage remarks in Pittsburgh revisited that earlier chapter in public comments delivered more than a decade after the relationship ended.
Simpson’s remarks came amid a broader public appearance at the benefit concert, where she performed and addressed the audience. The incident underscores how former personal and financial connections between high-profile figures can surface years after a relationship ends.
Simpson is currently finalizing a divorce from her estranged husband, former NFL player Eric Johnson, whom she married in July 2014; the couple share three children. Simpson was previously married to singer Nick Lachey from 2002 to 2006.
The boat dispute and Simpson’s onstage comments were first reported by Page Six, citing the fan video and the performer’s remarks during the concert. Additional details about the transaction and the transfer of title were not independently verified.