Jessica Simpson Roasts Ex-Tony Romo: Boat Drama and $100K Speedboat Surprise!
SIMPSON SLAMS ROMO: Country Crooner Roasts Ex-Boyfriend Tony Romo Over Awkward Reunion and Petty Gift
In a juicy revelation that's got everyone talking, Jessica Simpson took to the stage at the 2025 Women Who Rock Benefit Concert in Pittsburgh earlier this month, dishing out some major shade towards her ex-boyfriend Tony Romo. The country-pop sensation, 45, spilled all about their past relationship and the awkward encounter they had recently after reconnecting.
As she regaled the audience with stories of her romantic misadventures, Simpson couldn't help but express her relief that they didn't end up together in the long run. "I'm glad we didn't work out," she quipped, as the crowd erupted into cheers and applause.
The Irresistible singer's comments came after Romo reached out to her through a rather...unconventional means: a phone call to her mom. Yes, you read that right – the former Dallas Cowboys quarterback got in touch with Simpson by calling her mom, Tina, because of a boat! It seems Romo was trying to sell the speedboat they had shared during their relationship and needed Jessica's signature on the paperwork.
But here's where it gets juicy: when Simpson finally spoke to Romo about the situation, he offered her a "thank-you gift" – a set of plastic cups! That's right, folks; after she spent approximately six figures on an over-the-top birthday present for him back in their twenties, this is what she got in return.
Simpson couldn't contain her amusement at Romo's thoughtless gesture. "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,' she said with a chuckle.
"And guess what he gave me as a thank you?" Simpson asked, raising an eyebrow. "Plastic cups!" The crowd was in stitches at this point, and it's easy to see why – who gives someone plastic cups after they spend six figures on a birthday gift?
The drama between Simpson and Romo dates back to their two-year relationship that fizzled out in 2009. At the time, Romo allegedly broke up with her just a day before her 29th birthday, leaving many wondering if he was simply too afraid to face his demons. In her 2020 memoir Open Book, Simpson opened up about their split and revealed that John Mayer's presence in her life had been the catalyst for their breakup.
Simpson and Mayer were hot-and-heavy at the time, with the Free Fallin' crooner reportedly having a "hold" on her that made it difficult for Romo to cope. "If John texted or emailed, I would hold up my phone and tell Tony immediately," she confessed in her memoir. "He knew the hold John had over me, and it was like telling your sponsor when you're triggered."
Now, with Simpson's divorce from estranged husband Eric Johnson still pending after a decade together, fans can't help but wonder what other secrets are waiting to be spilled. After all, this is an ex who spent six figures on her birthday gift – only to return the favor with some cheap plastic cups.
It seems Tony Romo learned his lesson the hard way: never underestimate the power of a girl scorned – especially not Jessica Simpson!
