Tony Romo dating history: All about former Cowboys QB’s love life before marriage

Tony Romo spent 14 seasons as a Dallas Cowboys quarterback. Before joining Dallas in 2003 as an undrafted free agent, he played for the Eastern Illinois Panthers' collegiate football team.

After that, Romo developed into one of the best quarterbacks in Cowboys history. He boasts many team records, notably passing yards, passing touchdowns and the most games with 300 yards or more in passing.

Tony Romo's popularity stemmed from more than just his football prowess; during his playing career, he was associated with numerous women. Notably, he dated artists Carrie Underwood and Jessica Simpson.

However, those women never wound up with the color analyst whom CBS Sports employs. Rather, Romo married Candice Crawford, the 2008 Miss Missouri USA.

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Tony Romo dated Carrie Underwood

Tony Romo, a well-known figure in American sports in the early 2000s. He used his prominence to his benefit in 2007 to date Carrie Underwood, a former contestant on American Idol, barely two years after she won the reality singing competition.

It's said that the two started dating in early 2007 and split up in October the same year. Carrie Underwood said that she and Romo were never truly serious following their breakup.

The popular country music singer said that Romo mistreated her, telling Esquire that her hit song "Cowboy Casanova" was unquestionably not about him.

"I would never make a man who wronged me immortal. She continued, "I would never give him that much credit.”

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Tony Romo also dated Jessica Simpson

It seems like Tony Romo has a penchant for blondes. He split up with Carrie Underwood, and in 2007, began dating Jessica Simpson, another blonde artist, with whom he remained until 2009.

Simpson and Romo initially connected in Nov. 2007 when the singer/artist's family went to see him perform. After introducing each other, they soon became friends and started chatting. They reportedly shared a kiss on their first date, demonstrating their affection for each other.

By Dec. 2007, the NFL had made much of Simpson's relationship, to the point where fans accused Simpson of distracting Romo during his poor performances. Simpson also faced backlash for being significantly overweight than when she began dating Romo.

Romo reportedly ended his romance with Simpson on the eve of her 29th birthday. Simpson is now wed to Eric Johnson, a former NFL player and has two kids, Maxwell and Ace.

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Tony Romo married Candice Crawford in 2011

After connecting at a Dallas Cowboys match, where Candice Crawford was a local intern pursuing a career in sports broadcasting, Romo and Crawford embarked on their love journey.

The pair experienced several special moments as their love story developed, such as Romo proposing to Crawford during a family dinner on her 24th birthday. Since their May 2011 wedding, the couple has welcomed three children into their home.

"If you get an amazing wife who knows the high standards of someone in sports, I think that's crucial," Romo said to PEOPLE in 2012. "I was fortunate enough to meet someone with that quality. She makes a fantastic wife and mother.”