Jessica Simpson told audience members at a recent benefit concert that she was glad her 2000s relationship with former Dallas Cowboys quarterback Tony Romo did not last, after an awkward reconnection over a jointly titled boat.
At the Women Who Rock Benefit Concert in Pittsburgh earlier this month, fan-shot footage shows Simpson, 45, recounting that Romo contacted her mother to say he was selling the boat but that Simpson’s name remained on the title. "He's calling my mom, saying, 'Well, Tina, I'm selling the boat.' And my mom's like, 'OK, and?'" Simpson said. "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. 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 and Romo, both 45, dated for about two years before splitting in 2009. The singer recounted the episode amid a performance and between remarks about other moments in her life. The anecdote references a widely reported earlier gift: tabloids have previously claimed Simpson spent roughly $100,000 on a speedboat for Romo’s 28th birthday in 2009, a figure cited by the National Enquirer.
In her 2020 memoir Open Book, Simpson described the end of her relationship with Romo and wrote that another past relationship — with musician John Mayer — had put strain on their romance. Simpson said in the memoir that Mayer had a hold on her at the time and that she would immediately inform Romo when Mayer contacted her.
Simpson’s comments come as she continues to navigate a public divorce from estranged husband Eric Johnson after about a decade together. Simpson and Johnson share three daughters: Maxwell, Ace and Birdie. Romo has been married to journalist Candice Crawford since 2011.
The anecdote about the boat circulated online after footage of Simpson’s onstage remarks was shared by attendees. The singer’s remark that she received plastic cups as a thank-you drew laughter from the crowd and was framed by Simpson as proof the relationship had not been a good fit.
The episode adds to a string of public moments for Simpson this year, including the release of cover art for a new single and promotional appearances tied to her music career. Representatives for Simpson and Romo did not immediately respond to requests for comment.
The two were public figures in the 2000s pop culture landscape: Simpson rose to fame as a pop and country singer and actress, while Romo became a high-profile NFL quarterback. Their relationship and subsequent break-up have been revisited in media accounts over the years as both moved into new relationships and careers.
Simpson’s recounting focused on the immediate awkwardness of the recent contact and used humor to underscore her view of the old relationship. She did not indicate any further personal interaction with Romo beyond completing the paperwork to remove her name from the boat title.