Jessica Simpson Shares Awkward Tony Romo Boat Sale Details

Jessica Simpson recently shared an awkward interaction with her ex-boyfriend Tony Romo, the former Dallas Cowboys quarterback, during the 2025 Women Who Rock Benefit Concert. Romo contacted Simpson's mother to notify them about selling a $100,000 speedboat they had purchased together during their relationship, but since Simpson's name was still on the title, she had to sign paperwork to transfer ownership. After completing the sale, Romo reportedly thanked Simpson with plastic cups, a gesture she found odd and used to reflect on why they did not stay together. The story drew reactions from Cowboys fans who viewed Romo's gift as a humorous or "savage" move. Simpson also discussed her supportive family dynamic with her ex-husband Eric Johnson while attending her sister Ashlee Simpson's concert residency, highlighting their united front despite past relationships. Additionally, Simpson made a notable return appearance at the 2025 MTV Video Music Awards, attracting attention for both her performance and changed appearance.