Before Tony Romo became the voice of CBS football, he was the most scrutinized man in Dallas. It wasn’t just the interceptions or the bobbled snaps. It was the paparazzi. For a solid four-year stretch, Romo’s dating life was basically a national pastime.
Honestly, the Tony Romo ex girlfriends list reads like a mid-2000s red carpet lineup. You’ve got pop stars, country legends, and Hollywood actresses. Most people remember the Jessica Simpson drama, but there's a lot more to the story than just a "jinx" at a football game.
The Carrie Underwood Era: A Small Town Collision
In 2006, Romo started dating Carrie Underwood. She was fresh off her American Idol win. He was the rising star of "America's Team." On paper, it was a Texas fairytale. They even walked the ACM Awards red carpet together in 2007.
But it didn't last.
Underwood later hinted that Romo wasn't exactly ready for a serious commitment. She told Esquire that he was "more into football" than her. There’s a bit of a sting there, right? She even famously said she wouldn’t "immortalize" him in a song because he didn't deserve the credit.
"I don't think he's at the point in his life where he would be willing to sacrifice football," Underwood told Entertainment Weekly back in 2007.
It’s kinda wild to think about now. They were both small-town kids dealing with massive, sudden fame. Sometimes that helps people bond; other times, it just creates a lot of noise. By mid-fall of 2007, "Romowood" was officially over.
The Jessica Simpson Saga and the "Jinx"
If the Underwood relationship was a quiet country song, the Jessica Simpson era was a full-blown tabloid rock opera. They started dating in late 2007. This was peak paparazzi culture. Every time Simpson showed up to a Cowboys game wearing a pink Romo jersey, the media lost its mind.
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Then came the "jinx."
The Cowboys lost a playoff game to the Giants after Romo and Simpson took a vacation to Cabo during a bye week. Fans blamed her. It was unfair, sure, but that’s Dallas for you.
The real end of their relationship was way more dramatic than a football loss. In her memoir Open Book, Simpson revealed that Romo broke up with her in July 2009. The reason? He saw a text from her ex, John Mayer.
- The Date: July 2009 (The night before her 29th birthday).
- The Cause: A "non-cheating" text from John Mayer.
- The Delivery: Basically an immediate breakup.
Simpson claimed she hadn't cheated, but Romo wasn't having it. Just like that, two years were gone.
The Sophia Bush Rumors and Others
There was a brief moment in late 2007 where things got confusing. While the media was tracking Romo's every move, he was spotted out with One Tree Hill star Sophia Bush.
They went to a few dinners. People started speculating. But Bush eventually cleared the air, saying they realized pretty quickly they were just meant to be friends. They were looking for different things.
There were even wilder rumors. Remember when Ryan Seacrest claimed Britney Spears gave Romo a lap dance? Most of that was just the 2000s rumor mill spinning out of control. When you're the Cowboys QB, if you stand next to a celebrity for five seconds, the tabloids print a wedding date.
Finding "The One" with Candice Crawford
By 2009, Romo was done with the pop star circuit. He met Candice Crawford, a sports reporter and former Miss Missouri USA.
The story goes that he "tricked" her into their first date by saying a group of people were going to a movie, but it ended up just being them. It worked. Romo has said he knew after just two dates that he was going to marry her.
Funny enough, Candice is the sister of Chace Crawford, the Gossip Girl actor who—wait for it—actually dated Carrie Underwood. It’s a very small world in the celebrity dating pool.
Romo and Candice married in 2011. They have three sons now: Hawkins, Rivers, and Jones. It seems the "wild" dating years provided exactly what Romo needed to figure out what he actually wanted in a partner.
Key Takeaways for the Romo Timeline
If you're looking for the "why" behind the headlines, it usually comes down to three things:
- Timing: Romo was at the peak of his career and the center of Dallas culture. Anything he did was going to be magnified 10x.
- Pressure: Dating a high-profile athlete while they are struggling on the field (the "Jinx" era) is a recipe for disaster.
- Communication: Based on Simpson's account, Romo had a very "all or nothing" approach to trust.
If you want to understand the cultural impact of this era, look at how the media treats Travis Kelce and Taylor Swift today. Romo and Simpson were the blueprint for that kind of intense, often invasive, crossover between sports and entertainment.
To dig deeper into this era of Dallas history, you can check out the local archives of the Dallas Morning News or pick up a copy of Jessica Simpson's Open Book for her side of the 2009 split.