Tony Romo Dated Jessica Simpson 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.

Who was Tony Romos first wife?

Candice Crawford When Tony Romo first asked his now-wife, Candice Crawford, to dinner and a movie, the aspiring broadcaster was living with her parents. Candice was an intern at the time, and had been allowed to interview a few players—which is how she met Tony.