Jessica Simpson Reveals She Reconnected with Ex-Boyfriend Tony Romo and Why She's 'Glad We Didn't Work Out'

Jessica Simpson thinks splitting from Tony Romo was for nan best.

The "With You" singer, 45, performed astatine nan 2025 Women Who Rock Benefit Concert astatine Stage AE successful Pittsburgh connected Friday, Sept. 5 and said to nan crowd mid-show astir precocious reconnecting pinch Romo, 45, aft they dated from November 2007 to July 2009.

"A mates weeks agone my mom sewage a telephone call," said Simpson, according to a instrumentality video from nan show. "And he's calling my mom, saying, ‘Well, Tina, I’m trading nan boat.’ And my mom’s like, ‘Okay, and?’”

"He’s for illustration ‘Well, Jessica’s sanction is still connected nan title,’" she added. "So, past I get paperwork, and I person to motion complete this vessel for him to sell."

"And conjecture what he gave maine arsenic a convey you? Plastic cups," said Simpson. "I’m like, ‘Wow, I’m gladsome we didn’t activity out.'"

In 2009, nan National Enquirer reported nan "A Public Affair" creator purchased a $100,000 speedboat for Romo arsenic a gift.

Simpson, who shares 3 kids pinch ex-husband Eric Johnson, reflected connected making love Romo successful her 2020 memoir Open Book and explained their divided was caused by her remaining successful interaction pinch ex John Mayer.

PEOPLE caught up pinch Simpson (whose separation from Johnson was announced successful January aft 10 years of marriage) astatine nan 2025 MTV VMAs earlier this month, and she revealed who she wants to triumph this year’s Sexiest Man Alive title.

"I mean, location are a batch of group who are sexy," she said coyly. "I'm single, truthful everybody's sexy correct now!"

After listing Charlie Hunnam, James Franco and Jamie Dornan as her apical picks, Simpson added, "There are a batch of hotties… There are a batch of tiny guys retired there."

Simpson's latest EP, Nashville Canyon, Pt. 2, was released connected Sept. 5 and features songs including "Savage" and "Your Apology."