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.

Born in Dallas, Texas in 1980, Simpson started her musical career in Christian music before crossing over to pop. Her movie and television career did not start until she joined husband Nick Lachey of 98 Degrees in an MTV reality show called The Newlyweds. Following the couple's divorce in 2005, she made her film debut as Daisy Duke in The Dukes of Hazard and later starred with Dane Cook in Employee of the Month. Her musical albums included hits like “I Wanna Love You Forever” and “I Think I’m in Love.”

Romo was born in San Diego, California, the son of a Navy sailor. He signed on as an undrafted free agent with the Dallas Cowboys in 2003 after receiving calls from the Cowboys, Denver Broncos, Arizona Cardinals, Detroit Lions, and Miami Dolphins on draft day. His shot to the top quarterback spot was not an instant one, as he worked his way from third string to his current starting position.