Tony Romo

Dallas Quarterback, Tony Romo, was once in a relationship with country singer Jessica Simpson back in the day, and they were considered the “It” couple. The pair looked great together when they were spotted out on dates. Though many were shipping the two to walk down the aisle, the pair ended their romance just two years in. What was the cause of the split? Rumors have said that another singer, John Mayer to be exact, was reported to be interested in his gal. More fuel was added to the fire when Simpson and Meyer met.

Though the singer later said that nothing happened between them, Romo believed otherwise and ended their relationship right then and there. But after finding out that she was telling the truth, it was too late to reconcile with his beau. He did end up marrying Candice Crawford, a former contestant for Miss USA and now working as a TV journalist. The quarterback’s investment money was spent on their wedding and their three children.