Jessica Simpson has never been one to shy away from sharing a good story, and her latest revelation had fans laughing and listening closely. The pop star turned fashion mogul, who shot to fame in the late 1990s with her powerhouse vocals and bubbly personality, took the stage at the 2025 Women Who Rock Benefit Concert in Pittsburgh with more than just music on her mind.
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Between songs, she recalled an unexpected phone call from ex-boyfriend Tony Romo – the former Dallas Cowboys quarterback – who had a rather unusual reason for getting back in touch. The story involved a six-figure speedboat, some paperwork, and a thank-you gift that was anything but glamorous.
Tony Romo’s surprising call about a speedboat
Speaking on stage, Jessica explained that her ex-boyfriend had unexpectedly tried to reach out more than a decade after their split. According to Hello! Magazine, the former Dallas Cowboys quarterback called Jessica’s mother, Tina Simpson, with a very specific request. Jessica recalled:
He’s calling my mom, saying, “Well, Tina, I’m selling the boat.” And my mom’s like, “OK, and?”
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 no ordinary gift – it was a $100,000 speedboat Simpson had given Romo for his 28th birthday in 2009, during their two-year romance. What amused the audience even more was her description of Romo’s thank-you gesture. She continued:
And guess what he gave me as a thank you? Plastic cups! I’m like, “Wow, I’m glad we didn’t work out.”
A look back at Jessica’s relationships
Jessica and Romo’s breakup in 2009 became a talking point at the time. As reported by Hello! Magazine, Romo allegedly ended the relationship the day before her 29th birthday.
Simpson later opened up about the split in her 2020 memoir Open Book, where she candidly revealed that her ongoing connection to musician John Mayer had played a role.She wrote:
If John texted or emailed, I would hold up my phone and tell Tony immediately.
He knew the hold John had over me, and it was like telling your sponsor when you’re triggered.
She explained that Mayer’s influence on her life had created tension in her relationship with Romo, ultimately contributing to their separation.
Fast forward to 2025, and Jessica’s love life is still a subject of public curiosity. Earlier this month, she confirmed on the red carpet of the MTV Video Music Awards that she is currently single. She said with a smile:
There’s a lot of people who are sexy! I’m single, so everybody is sexy right now… there’s a lot of hotties.
Her openness about dating was further highlighted during an interview on TODAY with Jenna & Friends in July. When asked if she was ready to be set up, Jessica responded:
I’d totally jump on that. Yes I’m single – very into like, very… I’m ready! My type of person is one of a kind. I don’t have a look, or anything. I just like for somebody to be individually, who they are. And exude confidence without the ego.
Her current single status follows the end of her 10-year marriage to Eric Johnson. In January, she shared with 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.
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Hello! Magazine: Jessica Simpson reveals NFL ex-boyfriend contacted her 16 years after split
