In terms of star status, there aren't many superstar 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 with the Dallas football team, where he won 78 games (but not a whole lot in the playoffs), threw 248 touchdowns 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 alongside Jim Nantz in the booth for CBS Sports as a color analyst. 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 when he was a free agent on the dating scene. 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. Romo and Jessica 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. Romo and Carrie Underwood dated briefly in 2007 before he and Simpson were an item. The NBC Sunday Night Football theme song singer and former American Idol winner linked up with the zero-time Super Bowl winner and briefly dated before things turned sour. Crazy enough, Underwood went on to date Romo's future brother-i