BroBible
Pop star Jessica Simpson famously (or infamously depending on your perspective) dated former NFL quarterback Tony Romo from 2007 to 2009. 16 years later, she is still talking about him.
Simpson, who announced she was splitting from her husband, former NFL tight end Eric Johnson, in January, made her comment about Tony Romo while on stage during the 2025 Women Who Rock Benefit Concert in Pittsburgh over the weekend. The reason for her comments was a strange one. It related to a $100,000 speedboat Simpson reportedly gave to Romo in 2009 for his 28th birthday.
“A couple weeks ago, my mom got a phone call,” Jessica Simpson randomly informed the crowd at the concert. “And he’s, like, calling my mom, saying, ‘Well, Tina, I’m selling the boat.’ And my mom’s like, ‘Okay, and?’
“And he’s like ‘Well, Jessica’s name is still on the title,’” the 45-year-old singer continued. “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! Honestly. Plastic cups. I’m like, ‘Wow I’m glad we didn’t work out.'”
@jordycray Oh, Tony For context, she gifted the boat for his birthday! #jessicasimpson #tonyromo #popculture #cowboys #fyp ♬ original sound – jordycray
For the record, Tony Romo has been married to Candice Crawford since May of 2011. Simpson and Johnson were married in 2014. Why on Earth would she feel like dissing Romo now? Many of the commenters on video of Jessica Simpson’s bizarre call-out of Romo had thoughts.
“Why would she talk about that on stage? Also, the plastic cups were symbolic of her ‘sparkle cups.’ Iykyk,” read one comment.
“Well, yeah, Jessica you cursed the Cowboys for how long?” another viewer commented, echoing several others.
“He lives in her head rent free. He was just doing his due [diligence] to sell the boat. Got the signature, and sent her a gift basket out of courtesy,” someone else wrote.
“Sounds like she never got over Tony,” another person suggested.
“Tell us your bitter without telling us you’re bitter,” commented another viewer.
The post ‘Glad We Didn’t Work Out’: Jessica Simpson Randomly Throws Shade At Ex Tony Romo During Concert appeared first on BroBible.
