By SHARON MAI, ENTERTAINMENT REPORTER
Published: 00:14 EDT, 16 September 2025 | Updated: 00:15 EDT, 16 September 2025
Jessica Simpson roasted her ex-boyfriend Tony Romo after they recently reconnected in an awkward encounter.
The country-pop crooner, 45, admitted she was 'glad we didn't work out' while reflecting on their past relationship over 16 years after they called it quits.
She also revealed the shockingly underwhelming thank-you gift he gave her after she spent approximately six figures on an over-the-top birthday present for him, back in their twenties.
While performing at the 2025 Women Who Rock Benefit Concert in Pittsburgh earlier this month, fan-taken footage showed the Dukes of Hazzards star telling her audience about how her ex had recently reached out to her unexpectedly.
She said that the former Dallas Cowboys quarterback got in touch by calling up her mom because of a boat of all things.
Her comments about her ex comes amid her ongoing divorce from estranged husband Eric Johnson and after dropping the sexy cover art for her new single.
Jessica Simpson, 45, roasted her ex-boyfriend Tony Romo, 45, after they recently reconnected in an awkward encounter
Romo pictured in 2022
Recalling how the awkward encounter with Romo went down, she said: '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 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?' Simpson added. 'Plastic cups!'
'I'm like, "Wow, I'm glad we didn't work out,"' she said as the audience cheered.
The Irresistible singer was seemingly referring to the reported $100,000 speedboat she previously gifted her then-boyfriend for his 28th birthday in 2009, per the National Enquirer.
Simpson and Romo previously dated for two years before their romance fizzled out in 2009.
He allegedly broke up with her the day before her 29th birthday that same year.
In her 2020 memoir Open Book, Simpson opened up about their split and said that John Mayer was the reason they separated.
She previously dated the country singer and said that she would still talk to her ex, which added tension in her and Romo's relationship.
The country-pop crooner admitted she was 'glad we didn't work out' while reflecting on their past relationship, over 16 years after they called it quits; pictured July 2008
While performing at the 2025 Women Who Rock Benefit Concert in Pittsburgh earlier this month, fan-taken footage showed the Dukes of Hazzards star telling her audience about how her ex had recently reached out to her unexpectedly
She said that the former Dallas Cowboys quarterback got in touch by calling up her mom because he wanted to sell a boat that still had Jessica's name on the title; Romo pictured 2006
Simpson and Romo previously dated for two years before their romance fizzled out in 2009. He allegedly broke up with her the day before her 29th birthday that same year; pictured with Tiger Woods in 2009
Simpson had an on-off romance with John Mayer (not pictured) from 2006 to 2010 when she wasn't dating Romo; pictured August 2008 in Malibu
She admitted that the Free Fallin crooner still had a 'hold' on her at the time.
'If John texted or emailed, I would hold up my phone and tell Tony immediately,' she said. 'He knew the hold John had over me, and it was like telling your sponsor when you're triggered.'
Simpson had an on-off romance with Mayer from 2006 to 2010 when she wasn't dating Romo.
Before then, she was married to Nick Lachey from 2002 to 2006.
She is currently in the midst of divorcing her estranged husband Eric Johnson after a decade together. The pair share three daughters: Maxwell, Ace and Birdie.
Romo has been married to journalist Candice Crawford, the 38-year-old sister of Gossip Girl star Chace Crawford, since 2011.
Jessica SimpsonDallas Cowboys