Tony Romo Dated Jessica Simpson & Carrie Underwood Before Finding Love

Carrie Underwood

In terms of star status, there aren’t many athletes in Texas as famous as former Dallas Cowboys quarterback Tony Romo. The four-time Pro Bowl football player spent his entire 13-year NFL career in Dallas, where he won 78 games (but not a whole lot in the playoffs) and penciled himself in as one of the franchise’s greatest passers.

Romo retired in 2017, transitioned to sports broadcasting and now makes more money than many current NFL quarterbacks calling games in the booth for CBS Sports. It’s no surprise that someone of Romo’s stature ended up marrying a former beauty pageant queen who competed in Miss USA, but he also dated two bombshell country music stars.

Romo’s lack of success in the postseason is well-documented (remember the playoff fumble?), but he’s never had a problem scoring some of the most beautiful and famous celebrities. Let’s take a closer look at some of those relationships. Unsurprisingly, he ended up with a former Miss USA contestant like Tim Tebow and Christian McCaffrey.


Romo and Simpson were the “it” couple when they dated from 2007 to 2009. They reportedly began dating in November 2007.

In December 2007, she was spotted at his game between the Cowboys and Philadelphia Eagles. They stirred the sports media world when pictures of them at a Cabo San Lucas resort surfaced before a pivotal playoff loss to the New York Giants.

Romo broke up with the singer and Dukes of Hazzard star in 2009 right before her 29th birthday. He reportedly broke up with her after she met John Mayer and suspected something happened between them. The kicker? He broke up with her via email.

I guess she found out those boots really were made for walking…right out of his life.

WATCH Tony Romo Dating History VIDEO BELOW:

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