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.

How long did Romo and Jessica Simpson date?

After 11 years, Jessica Simpson is sounding off on her 2009 split from former Dallas Cowboys quarterback, Tony Romo, ending their two-year relationship.

When was Jessica Simpson with Tony Romo?

Tony Romo and Jessica Simpson were one of the biggest “it” couples more than a decade ago. The Dallas Cowboys quarterback and the pop star were a dream match for celebrity gossipers. The relationship, which began in 2007, didnt last.

Who was Tony Romo engaged to?

Candice Crawford received a very special gift from Tony Romo for her 24th birthday this year: a ring and a marriage proposal.