Simpson's Occupation:
Actress and singer
Romo's Birth Date:
April 21, 1980
Simpson's Birth Date:
July 10, 1980
Romo's Team:
Dallas Cowboys
Dated:
2007-2009
 
Although Jessica Simpson announced her engagement to former NFL player Eric Johnson in 2010, her first round as an NFL girlfriend was played with Dallas Cowboys quarterback Tony Romo. Romo and Simpson, were linked romantically from 2007 until he broke up with her on the night before her 29th birthday.
 
Shortly after the breakup, the two were seen at the same White House Correspondents dinner but he was with new girlfriend, and now fiancee, Candice Crawford. The Washington Post reported Simpson looked miserable at the event. The Romo and Simpson relationship began after he commented he had a crush on the actress and singer prompting her representatives to contact his and set up a date for the two.