Jessica Simpson recalls surprising post-breakup moment with Tony Romo

Jessica Simpson is "glad" that things did not work out between her and ex boyfriend Tony Romo.

In a recent video shared by a fan on the internet, the songstress spoke about her former boyfriend during her gig at the 2025 Women Who Rock Benefit Concert at Stage AE in Pittsburgh on Friday September 5.

She told the crowd that Tony recently reconnected to her through her mom.

For the unversed, the pair dated from November 2007 to July 2009.

"A couple weeks ago my mom got a phone call," said Simpson in the clip. "And he's calling my mom, saying, ‘Well, Tina, I’m selling the boat.’ And my mom’s like, ‘Okay, and?’”

She went on to recall, "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."

"And guess what he gave me as a thank you? Plastic cups," Simpson added. "I’m like, ‘Wow, I’m glad we didn’t work out.'"

Back in 2009, the With You singer gifted a $100,000 speedboat for Tony as per National Enquirer.

Jessica also talked about her relationship with Tony in her memoir revealing their break up occurred because she kept in touch with ex John Mayer.