More than 15 years after Jessica Simpson and Tony Romo called it quits, the “With You” singer shared rare insight into a recent interaction her mom Tina had with the former Cowboys quarterback.
Jessica Simpson knows that some love isn’t meant to last forever.
Over a decade after she and Tony Romo officially called it quits, the “I Wanna Love You” singer seemingly detailed a recent interaction between the two.
“A couple weeks ago, my mom got a phone call,” Jessica said onstage during the 2025 Women Who Rock Benefit Concert in Pittsburgh, Pennsylvania, as seen in videos shared on social media. “He’s calling my mom, saying, ‘Well, Tina, I’m selling the boat.’ And my mom’s like, ‘Okay, and?’”
Back in 2009, Jessica allegedly gifted the former Dallas Cowboys quarterback a $100,000 speedboat, according to the National Enquirer at the time, in celebration of his 28th birthday.
“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 once all was said and done, the 45-year-old claimed that Tony thanked her with quite an interesting gift: plastic cups.
She quipped, “I’m like, ‘Wow I’m glad we didn’t work out.’”
Jessica’s rare comments about her ex, whom she dated from 2007 to 2009, came just days before she walked the red carpet at the MTV VMAs for the first time in nearly 20 years.
And as she stunned in a black lace Christian Siriano gown, the “Irresistible” singer also shared insight into how she and her ex-husband Eric Johnson—who divorced in 2010—supported her younger sister Ashlee Simpson as she kicked off her “I Am Me” residency in Las Vegas last month.
“We are all a big, happy family, so it’s important for all of us,” Jessica—who shares kids Maxwell, 13, Ace, 12 and Birdie, 6, with Eric—told E! News on the 2025 MTV Video Music Awards red carpet Sept. 7. “We wouldn’t have missed Ashlee, are you kidding me? It was such a moment.”
As a big sister, the artist went on to reflect on the emotional experience of watching Ashlee alongside their parents Joe Simpson and Tina Ann Drew.
“I was a mess,” she admitted. “I cried probably seven times. I think I know her lyrics better than my own old songs.”
For his part, Tony retired from the Cowboys in 2017 and has since kickstarted his career in sports journalism while raising sons Hawkins, 11, River, 8, and Jones, 5, with wife Candice Romo.
“If you get a great wife who understands the demands of someone in athletics, I think that’s important,” Tony told People of his wife in 2012. “I was lucky enough to find someone like that.”
“She’s a great mom and a great wife,” he added. “It’s been fun just hanging out with her and my son. It’s been exciting.”
For a deeper dive into Jessica’s star-studded dating history, keep reading…
Simpson began dating her current husband, a retired NFL tight end, in summer of 2010. They welcomed their first child, daughter Maxwell Drew Johnson, in May 2012, and their second, son Ace Knute Johnson, in June 2013. Simpson and Johnson wed the following summer. In March 2019, she gave birth to their third child, daughter Birdie Mae Johnson.
In January 2025, the pair shared that they were going their separate ways following 10 years of marriage.
“Eric and I have been living separately navigating a painful situation in our marriage,” Jessica told E! News in a statement at the time. “Our children come first, and we are focusing on what is best for them. We are grateful for all of the love and support that has been coming our way, and appreciate privacy right now as we work through this as a family.”
The two singers dated on and off for almost a year since summer of 2006, several months following her split from husband Nick Lachey. Simpson opened up about her relationship with Mayer in her 2020 memoir, Open Book. She said he repeatedly told her “he was obsessed with me, sexually and emotionally.”
Mayer had told Playboy in 2010 that Simpson was like “crack cocaine” to him, adding, “Sexually it was crazy. That’s all I’ll say. It was like napalm, sexual napalm.”
This did not sit well with his ex. “He thought that was what I wanted to be called,” Simpson wrote in her memoir. “I was floored and embarrassed that my grandmother was actually gonna read that.”
Two years later, Mayer expressed regret about his comments, telling NPR, “I had nothing to say. I was going through a time in my life where I didn’t really want to share what was going on, but I didn’t want to be boring.”
Simpson also wrote in her book that she was constantly worried she “wasn’t smart enough” for Mayer, adding, “My anxiety would spike and I would pour another drink. It was the start of me relying on alcohol to mask my nerves.”
On April 1, 2020, Mayer said on Watch What Happens Live With Andy Cohen that he had “heard some bits” about Simpson’s memoir, adding, “But as Pee Wee Herman says in Pee Wee’s Big Adventure before the movie of his life is about to play out at the end, he’s not watching the movie, and the reason he’s not watching the movie, he says, ‘I don’t have to watch it, Dottie, I lived it.’ And I think that’s prescient here.”
Simpson married the fellow singer in 2002 after almost four years of dating, and she reportedly lost her virginity on their wedding night.
Their marriage was documented on the MTV reality show Newlyweds: Nick and Jessica, which aired between 2003 and 2005 and contained the now-infamous moment in which Simpson ate canned tuna and uttered the line, “Is this chicken, what I have, or is this fish? I know it’s tuna but it says, ‘Chicken By the Sea.’ Is that stupid?”
Simpson and Lachey split in 2005. They had no children together.
In a new excerpt for the paperback release of her memoir, she detailed her heartbreak after learning Lachey had moved on with now-wife Vanessa Lachey. As Jessica wrote in the diary entry, according to Entertainment Tonight, “So, Nick, you’re with another already? Seems that you forgot the love you spoke to me… I’m saddened beyond belief. Alone in the dark, with no one to call my own.”
Simpson and the Dallas Cowboys quarterback began dating in late 2007 and split less than two years later. He broke up with her the night before her 29th birthday.
“She was surprised. She wouldn’t have planned a party if she knew this was coming,” a source close to Simpson told E! News at the time. “They’re both going their separate ways.”
She and the Smashing Pumpkins frontman sparked romance rumors in late 2009. Months later, she told E! News she was “single” and called Corgan a “dear dear friend of mine.”
“If I am going through a hard time I definitely would talk to Billy,” she added. “He always has the best words.”
Back in the late ’90s, she reportedly dated the Supernatural star. On her and now-ex-husband Nick Lachey‘s MTV reality show Newlyweds: Nick & Jessica, the singer revealed that she had her heart broken by an “actor on Days of our Lives.” Neither Simpson nor Ackles has confirmed a past relationship with each other on the record.
The two sparked romance rumors in 2004 while she was still married to Nick Lachey. Neither has confirmed a past romance.
Simpson and the Jackass star, who appeared with her in the Dukes of Hazzard film reboot, sparked romance rumors in 2005. In her book, she revealed she had an emotional relationship with him, which she believed was actually “worse than a physical one.”
“After I actually had sex, I understood that the emotional part was what mattered,” she wrote. “And Johnny and I had that, which seemed far more of a betrayal to my marriage than sex.”
Source: www.eonline.com