Jessica Simpson has revealed that her ex-boyfriend, NFL star Tony Romo, reached out to her 16 years after their breakup. The 45-year-old singer shared the story while performing at the 2025 Women Who Rock Benefit Concert in Pittsburgh.
According to Simpson, the former Dallas Cowboys quarterback contacted her mother to ask about a boat. 'He's calling my mom, saying, 'Well, Tina, I'm selling the boat.' And my mom's like, 'OK, and?'' she recalled. '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 that Simpson had gifted Romo for his 28th birthday in 2009. The couple dated for two years before splitting in 2009, with Romo allegedly ending the relationship the day before Simpson's 29th birthday.
Simpson also shared the underwhelming thank-you gift she received from Romo. 'And guess what he gave me as a thank you?' she added. 'Plastic cups!' She continued: 'I'm like, 'Wow, I'm glad we didn't work out.''
In her 2020 memoir 'Open Book', Simpson cited John Mayer as the reason for the breakup, explaining that Mayer's texts and emails created tension in her relationship with Romo.
