TBT: Jessica Simpson and Tony Romo Kissed "10 Minutes" Into Their First Date

“I had butterflies that you would not imagine,” said Simpson.

TBT: Jessica Simpson & Tony Romo
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Who: Singer, actress, and fashion designer Jessica Simpson, 42, and former Dallas Cowboys quarterback Tony Romo, 42. 

How They Met: Romo had a crush on Simpson before they even met. According to Jessica, she was watching a football game at home with her family in November 2007 when the former NFL star told reporters that she was his dream celebrity crush. 

“My family was like, 'Did you just hear that?" Simpson said in the June 2008 issue of Glamour. "His picture came up, and I'm like, 'He's really cute.' Then I heard [that I was his crush], and I'm like, 'Oh my gosh!'” 

They met after a mutual friend introduced Tony to Jessica’s dad, Joe Simpson, and soon the pair went on their first date. "I had butterflies that you would not imagine,” she recalled to Glamour. “I wanted to puke in the cup holder … It took me forever to put together an outfit!" 

TBT: Jessica Simpson & Tony Romo

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Once at dinner, the nerves settled, and they got cozy with each other — fast.  

“The fact that this guy, on our first date, in the first 10 minutes of dinner, wanted to lean over the table and say, ‘This is my girl, and I want to kiss her' – our first kiss in front of everybody – was awesome,” Jessica remembered. Days later, they spent Thanksgiving together in Texas, and before everyone knew it, Jessica was cheering on Tony from the stands in her iconic pink Cowboys jersey

Why We Loved Them: They didn’t let the haters get them down. Just months into their relationship, Cowboy fans nicknamed Jessica “Yoko Romo,” blaming her for Tony’s poor performance and the team’s 2008 losing streak. Addressing the “jinxing” drama on The Late Show with David Letterman, Simpson vowed never to wear her infamous pink #9  jersey again. 

“I really think it’s because I was wearing a pink No. 9 jersey and not a blue one,” Jessica said, adding that since she switched colors, the Cowboys have been “doing great.”

While not everyone was a Simpson-Romo stan at the time, the couple told Vanity Fair that they tend to tune out the drama. 

TBT: Jessica Simpson & Tony Romo

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"We don't let it affect our relationship," she said. "If we did, we wouldn't be together, because it happened at the very beginning. Dating the Cowboys quarterback comes with hype, the fans, the bloggers, but I've never dated a guy that was more simple. I'm always there for him after a game, and he knows he has me to come home to."

Romo also gave his opinion on the controversy. “She comes to a ton of games,” Romo said. “She’s a supportive girlfriend. You know, it’s very hard when you lose because games are important, and so many people put so much time and effort in. It’s nice to have someone to come home to and try to make you feel better.”

When They Peaked: When Jessica dedicated the song, “You’re My Sunday,” to Tony during a concert for her country album tour. With lyrics like, “When life is like a hurricane / Flying off the rails like a fast train / Everything around me is so insane / You come and take it all away / You're my Sunday” — it’s cheesy, but nonetheless, sweet. 

“My boyfriend is a football player, and he takes up my Sundays and now my Mondays,” Simpson said before introducing the song to the audience at the time, adding: “I am so happy!”

The Breakup: A year and a half into their relationship, Tony broke up with Jessica the day before her 29th birthday on July 10, 2009. Her Ken and Barbie-themed party was canceled, and Jessica celebrated quietly with friends and family, while Tony was spotted out in Los Angeles at MyHouse.  

“She is heartbroken,” a source told People. “She loves Tony. But it’s been difficult lately. He’s busy with his career, and she’s getting ready to shoot her show (The Price of Beauty). They decided to part ways.”

Eleven years later, Jessica finally spoke out about their “ugly” split in her memoir Open Book. “[Tony] accused me of seeing John [Mayer] behind his back,” Simpson wrote. “I hadn’t cheated on Tony at all. But I could not lie and say I hadn’t even seen [Mayer]." Simpson saw Mayer at her parents' house, and Romo found out through an email the singer sent her about the run-in. Insisting "nothing happened," Romo "didn't believe that for a second" and broke up with Simpson on the spot.  

She added that the “breakup had been so ugly that it shocked me into realizing it had been necessary.”

TBT: Jessica Simpson & Tony Romo

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Where They Are Now: The next summer, Jessica began dating her current husband, retired NFL tight end, Eric Johnson. In 2012, they welcomed their first child together, a daughter, Maxwell Drew, and a year later, a son named Ace Knute. The couple also shares a three-year-old daughter, Birdie Mae. 

Since 2009, Jessica’s singing career has taken a backseat, and the multi-hyphenate has focused most of her attention on her billion-dollar fashion brand. In October 2021, she and her mom, Tina Simpson, regained full ownership of the company after selling their majority stake to Sequential Brands Group Inc. in 2015. 

After splitting from Jessica, Tony began seeing 2008 Miss Missouri USA-winner Candice Crawford (she's also the sister to Gossip Girl alum Chace Crawford). The two got married in 2011 and they share three sons — Jones, 5, Rivers, 8, and Hawkins, 10.

Romo retired from football in 2017 following a preseason back injury the previous year. Upon his retirement, he was hired by CBS Sports as a lead NFL commentator.

#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.

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