Jessica Simpson shared that her ex-boyfriend, NFL star Tony Romo, reached out to her - 16 years after their breakup. The 45-year-old opened up about the encounter while performing at the 2025 Women Who Rock Benefit Concert in Pittsburgh. Jessica shared that the former Dallas Cowboys quarterback tried to get back in touch by calling her mom 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 singer went on to share the underwhelming thank-you gift Tony gave her. "And guess what he gave me as a thank you?" she added. "Plastic cups!" Jessica continued: "I'm like, 'Wow, I'm g

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