NEWSJessica Simpson Throws Shade at Ex Tony Romo: 'Glad We Didn't Work Out'
Jessica Simpson exclaimed she is 'glad' things didn't work out between her and Tony Romo.
Sept. 21 2025, Published 6:00 a.m. ET
Jessica Simpson didn't hold back when discussing her ex-boyfriend Tony Romo during the 2025 Women Who Rock Benefit Concert in Pittsburgh. Their unexpected reconnection over a boat led to some sharp remarks from the pop star.
"He's calling my mom, saying, 'Well, Tina, I'm selling the boat.' And my mom's like, 'OK, and?'" Simpson revealed to the enthusiastic crowd, as captured in a fan video. "He's like, 'Well, Jessica's name is still on the title.'"
Jessica Simpson and Tony Romo's relationship lasted from 2007 to 2009.
This incident occurred after Romo, who kept the boat since their split, needed Simpson's signature to finalize the sale. "So, then I get paperwork, and I have to sign over this boat for him to sell," she explained.
Simpson, 40, didn't stop there. "And guess what he gave me as a thank you?" she teased. "Plastic cups!"
This cheeky remark prompted cheers from the audience. "I'm like, 'Wow, I'm glad we didn't work out,'" she added.
Tony Romo called Jessica Simpson's mom about selling a boat she gave him.
The boat, rumored to be a $100,000 speedboat Simpson gifted Romo for his 28th birthday in 2009, became the centerpiece of their awkward reunion.
Simpson's relationship with the former Dallas Cowboys quarterback was one of the most highly publicized celebrity pairings of the late 2000s. The two dated from November 2007 to July 2009, and their romance was a constant subject of media scrutiny and public discussion.
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Tony Romo reportedly thanked Jessica Simpson with plastic cups.
Their relationship was particularly notable for the backlash it received from some Dallas Cowboys fans, who blamed Simpson for Romo's poor on-field performance. Dubbing her "the Jessica Jinx" or "Yoko Romo," these fans believed her presence at games and the media circus surrounding their relationship were a distraction for the quarterback.
In her 2020 memoir, Open Book, Simpson reflected on the relationship, admitting that her romance with musician John Mayer contributed to her split from Romo.
She wrote, "If John texted or emailed, I would hold up my phone and tell Tony immediately. He knew the hold John had over me, and it was like telling your sponsor when you're triggered."
Jessica Simpson said she’s now open to dating again after her split from Eric Johnson.
Simpson and Mayer had a tumultuous on-again, off-again relationship from 2006 to 2010. Currently, Simpson is in the process of a split from her estranged husband, Eric Johnson, whom she married in July 2014. The couple shares three children: Maxwell, Ace and Birdie.
Simpson has also leaned on close friends like Kim Kardashian as she grappled through her marital woes. Sources claim The Kardashians star has been "brutally honest" throughout her ordeal.
When asked about dating again, she expressed a mix of apprehension and excitement. "It's a rough road in the dating world," she told Jenna Bush Hager on Today With Jenna & Friends, adding she's "not getting on the apps yet."
She has also stated, "I'm ready... I love love. And I'm very passionate. I have a lot to give."
