Pop singer/OG of the ‘celeb-reality’ genre, Jessica Simpson, dragged her ex-boyfriend, Tony Romo, over a financial transaction of a boat during a charity concert.
The star of MTV’s Newlyweds: Nick and Jessica no longer appears on reality TV, but this proves that stirring up drama for public consumption is still in her blood.
@jordycray Oh, Tony 😂 For context, she gifted the boat for his birthday! #jessicasimpson #tonyromo #popculture #cowboys #fyp ♬ original sound – jordycray
Messy Jessy:
The ‘With You’ songstress spilled the tea to the crowd at the 2025 Women Who Rock Benefit Concert in Pittsburgh.
As per a fan video, Jessica dished on Tony. “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, Jessica’s mom then had to tell Jessica to sign over the paperwork. “I have to sign over this boat for him to sell.” ICYMI, Jessica reportedly gifted a $100,000 speedboat to the retired Dallas Cowboy for his 28th birthday in 2009.
“And guess what he gave me as a thank you?” Simpson, 40, teased. “Plastic cups!”
“I’m like, ‘Wow, I’m glad we didn’t work out,’” she continued, as the audience cheered.
If anyone needs their memory refreshed …
Tony and Jess started dating in September 2007. At the time, Jessica took a lot of heat for their romance. Cowboys fans actively blamed Jessica for Tony Romo’s poor performance on the field.
The exes dated for two years before the NFL alum allegedly broke up with the “Newlyweds” alum one day before her 29th birthday in 2009, with his speedboat in tow.
While Jessica Simpson’s romance with Tony expired, he remained a source of strength for the singer. In Jessica Simpson’s memoir, she detailed how Tony helped her rationalize how John Mayer manipulated her in their relationship.
Jessica became a household name, not for her music, but for her first marriage to 98° crooner Nick Lachey, who returned to reality TV to host and executive produce Netflix’s Love Is Blind.
