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 glad we didn't work out'."
Jessica Simpson in stripe shirt holding dog with and Tony Romo in blue hoodie and cap in 2008© Getty Images
Jessica and Tony in 2008
Jessica and Tony's relationship
The boat in question was a $100,000 speedboat that Jessica had gifted her former partner for his 28th birthday in 2009. The couple dated for two years before they called it quits back in 2009. Romo allegedly ended the relationship the day before Jessica's 29th birthday.
John Mayer in black blazer and cream sweater and Jessica Simpson in black dress© Getty Images
John and Jessica dated before her relationship with Tony
The split
Jessica opened up about the split in her 2020 memoir Open Book, and cited that John Mayer was the reason for the break up. "If John texted or emailed, I would hold up my phone and tell Tony immediately," she explained. "He knew the hold John had over me, and it was like telling your sponsor when you're triggered."
Jessica Simpson in white dress and trench and Eric Johnson in blue shirt and red cap© Getty Images
Eric and Jessica were married for 10 years
Relationship status
Earlier this month, Jessica confirmed that she is very much "single" on the red carpet of the 2025 MTV Video Music Awards, despite sparking speculation over her relationship status after reuniting with ex-husband, Eric Johnson. "There's a lot of people who are sexy! I'm single, so everybody is sexy right now… there's a lot of hotties," she shared. "There's a lot of cute guys out there."
photo of jessica simpson wearing black fur coat© Getty Images
Jessica is ready to start dating
Dating life
During an interview on TODAY with Jenna & Friends back in July, Jessica shared whether she was ready to start dating again. "Are you interested in dating? Can I set you up with anybody?" asked Jenna Bush-Hager. "I'd totally jump on that," replied Jessica. "Yes I'm single – very into like, very... I'm ready!" She continued: "My type of person is one of a kind. I don't have a look, or anything," shared the hitmaker. "I just like for somebody to be individually, who they are. And exude confidence without the ego."
Eric Johnson, Jessica Simpson, Birdie Mae Johnson, Ace Knute Johnson and Maxwell Drew Johnson pose at Barnes & Noble Union Square© Getty Images
Jessica and Eric with their children
Divorce
The former couple announced their split in January after 10 years of marriage. The singer shared the news via a statement made to US Weekly. "Eric and I have been living separately, navigating a painful situation in our marriage. Our children come first, and we are focusing on what is best for them," she explained.