Tony Romo's Ex-Girlfriends: Who Has The Former Quarterback Dated?

Each year, the Super Bowl brings out both the best NFL players of today and yesteryear. This year's Super Bowl LV is proving to be one for the history books, with famed Tampa Bay Buccaneers quarterback Tom Brady going head-to-head with Kansas City Chiefs rising star Patrick Mahomes. Even former Dallas Cowboys quarterback-turned-sportscaster Tony Romo is calling the 2021 Super Bowl "a legacy game," per CBS. 

This year's Super Bowl will also bring Hollywood's star power to the forefront. Brady, of course, is married to supermodel Gisele Bundchen, while halftime performer The Weeknd and model Bella Hadid have been dating on-and-off for years, and Romo has his own slew of famous exes — plus a celebrity brother-in-law, aka The Boys star Chace Crawford. So which A-listers has Romo dated? Hint: there are plenty of blonde bombshells in Romo's past, and quite a few familiar faces. Keep scrolling to find out more about his love life history, and who he is linked to today!

With all the celebrities slated to appear at Super Bowl LV, Tony Romo may have to dodge some exes! The former Dallas Cowboys star was an eligible bachelor back in the early 2000s, and took advantage of his spot in the limelight to woo American Idol alum Carrie Underwood in 2007, just two years after the country star won the reality singing competition. The picture perfect couple reportedly dated in early 2007, but broke up that October. 

While Underwood claimed she and Romo were never a serious couple, she told Esquire that her 2009 hit single "Cowboy Casanova" was definitely not about her football player ex. "I would never immortalize a guy that did me wrong. I would never give him that much credit," Underwood stressed. 

Post-split, Romo moved on with another blonde songstress: Jessica Simpson. The pair began dating in 2007 — could infidelity be how Romo did Underwood wrong? — and stayed together until 2009. Simpson revealed in her memoir Open Book that Romo dumped her due to unfounded cheating suspicions about her relationship with ex-boyfriend singer John Mayer, per TMZ.

Romo finally found happiness with yet another fair-haired beauty: Miss Missouri beauty queen Candice Crawford. The couple met when Crawford interned with the Dallas Cowboys, and were married in 2011. Her big brother, Gossip Girl star Chace Crawford, also approves of their union. The Romos have three sons together now, and are one big happy family today!

Although their romance lasted less than a year, the "Before He Cheats" singer had plenty to say about ex-boyfriend Tony Romo. Once a player, always a player, it seems.

Two years after their 2007 split, Carrie Underwood told Esquire that Romo definitely had a type. "Point blank, he is about football. I don't know if it's that I'm not quite his type of whatever, but I don't think he's at the point of his life where he would be willing to sacrifice football," Underwood continued. "He hated so much that people thought that he was paying more attention to me and that was causing him not to do well."

So was Underwood jealous of the Dallas Cowboys quarterback's fans? Not necessarily. On Jan. 6, 2007, when Romo was rumored to be dating Underwood, per D Magazine, Romo fumbled a game-losing snap against the Seattle Seahawks. The Cowboys' fans blamed Romo for his mind being elsewhere... perhaps on a certain blonde country crooner? Of course, Romo and Jessica Simpson's romance took a similar turn, though the two did have a longer relationship than he and Underwood. Keep scrolling to find out how Romo's fans were relentless in voicing their concerns over his love life!

Singer and fashion entrepreneur Jessica Simpson weathered the brunt of the Dallas Cowboys' fan hatred for being linked to Tony Romo. The pair began dating in 2007 — could infidelity be how Romo did Carrie Underwood wrong? — and stayed together until 2009. In December 2007, the "heavily favored Cowboys lost to the Philadelphia Eagles 10-6," according to People, and everyone in Dallas pointed the finger at Simpson standing in the stands. "At one point, the network even showed a montage of Simpson, 27, spliced with shots of Romo's bad throws... commentator Joe Buck noted, 'It's never easy to play in front of your girlfriend,'" the article stated.

By January 2008, the Dallas Cowboys' hatred for Simpson was palpable. "The singer/actress/shoe designer will likely avoid the Dallas Cowboys stadium after fans blamed her weekend trip to Mexico with quarterback Tony Romo for the Cowboys' defeat by the New York Giants," Today penned. Celebrities like Eva Longoria and Simpson's ex-boyfriend John Mayer came to Simpson's defense, with Mayer pointing out that Simpson is a proud Texan herself.

Even Romo's teammate Terrell Owens threw some shade at Simpson, according to ESPN. Romo ultimately dumped Simpson in July 2009, the night before her 29th birthday. Simpson revealed in her memoir Open Book that Romo dumped her due to unfounded cheating suspicions about her relationship with ex-boyfriend Mayer, per TMZ, and broke up with her via email, per Spun. Good thing Romo has seemingly matured in the years since!