Jessica Simpson is looking back at her past relationship with former Dallas Cowboys quarterback Tony Romo with humor, telling fans she is “glad” things did not work out between them. The singer and entrepreneur made the comments during her performance at the 2025 Women Who Rock Benefit Concert at Stage AE in Pittsburgh on Friday, September 5.
A fan shared a video online showing Simpson recalling an unexpected recent exchange with her ex-boyfriend. Simpson, 45, explained that Romo had recently reached out to her through her mother, Tina. The two famously dated from November 2007 until July 2009, a relationship that received wide attention at the time.
“A couple of weeks ago, my mom got a phone call,” Simpson told the audience. “And he’s calling my mom, saying, ‘Well, Tina, I’m selling the boat.’ And my mom’s like, ‘Okay, and?’” The singer went on to describe her surprise when she learned she still had ties to Romo’s property.
“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.” Simpson then joked about Romo’s gesture after she signed the documents. “And guess what he gave me as a thank you? Plastic cups,” she said. “I’m like, ‘Wow, I’m glad we didn’t work out.’”
According to the National Enquirer, Simpson had originally gifted Romo a $100,000 speedboat during their relationship in 2009. The mention of the boat and the “thank you” cups sparked laughter from the Pittsburgh crowd. Simpson has spoken before about her time with Romo.
In her 2020 memoir Open Book, she revealed that the relationship ended after Romo learned she had kept in contact with another ex, musician John Mayer. The disclosure led to the breakup shortly before her 29th birthday.
Now more than a decade later, Simpson appeared to look back on the experience with amusement rather than regret. Her remarks at the benefit concert added a playful moment to an event that celebrated women in music and raised awareness for women’s health initiatives.
Fans responded to the viral video with supportive comments, praising Simpson for her candid storytelling and ability to find humor in her past relationships. Though her romance with Romo ended years ago, the memory of a boat, a few plastic cups, and a laugh on stage showed how Simpson continues to weave personal history into her performances with charm and relatability.