Two weeks ago, when PEOPLE asked Tony Romo what he had planned for girlfriend Jessica Simpson‘s birthday, he said, “It’s a secret.” As it turned out, Simpson’s birthday surprise turned out to be a shocker: Although Romo had insisted that things between them were “going good,” the Dallas Cowboys quarterback ended their year-and-a-half relationship on July 9 – the night before the singer turned 29. After Simpson and her family went to see Romo play for the first time in November 2007, things moved pretty quickly – he even kissed her on their first date!
The alum dated Romo, 29, in 2007, but by October of that year, she seemed to have had enough. I don't know if it's that I'm not quite his type or whatever, but I don't think he's at the point in his life where he would be willing to sacrifice football," she said at the time.
"He hated so much that people thought that he was paying more attention to me and that was causing him to not do well.'' See photos of Hollywood's ugliest splits Romo went on to date — and dump — Jessica Simpson, who did admit to penning a song, "Back in My Old Boots," about the athlete.
(Jemal Countess/Getty Images for Saks Fifth Avenue)Antonio Pierce and wife Jocelyn Pierce attends a screening of "Kobe Doin' Work" during the 2009 Tribeca Film Festival at BMCC Tribeca Performing Arts Center on April 25, 2009 in New York City.
(Rob Loud/Getty Images for Tribeca Film Festival)Aaron Ross and Olympic Track & Field Champion Sanya Richards-Ross attend a cocktail reception hosted by Saks Fifth Avenue And Off The Field Players' Wives Association on January 30, 2014 in New York City. (Ethan Miller/Getty Images for Tabu Ultra Lounge)Jessica Simpson married former NFL tight end Eric Johnson on July 5, 2014.
(Jeff Schear/Getty Images)NFL Player, Eric Decker, and wife and Country Singer, Jessie James Decker attend PANDORA Jewelry Valentine's Day Collection launch event at Soho Grand Hotel on January 20, 2016 in New York City. (Adam Bettcher/Getty Images)Minnesota Vikings player Jared Allen and wife Amy Johnson arrive at Muhammad Ali's Celebrity Fight Night XVIII held at JW Marriott Desert Ridge Resort & Spa on March 24, 2012 in Phoenix, Arizona.
(Mike Coppola/Getty Images)Adrian Peterson and wife Ashley Brown walk the red carpet at the 2014 Starkey Hearing Foundation So The World May Hear Gala at the St. (Michael Buckner/Getty Images for CFN)Lauran Tuck and NFL player Justin Tuck walk the runway at the Saks Fifth Avenue And Off The Field Players' Wives Association Charitable Fashion Show on January 31, 2014 in New York City.
(Countess/Getty Images for Saks Fifth Avenue)Minnesota Vikings player Steve Hutchinson and wife Landyn Hutchinson attend the Starkey Hearing Foundation's "So The World May Hear Awards Gala" 2011 at River Centre on July 24, 2011 in St. (Adam Bettcher/Getty Images for Starkey Hearing Foundation)Britton Colquitt of the Denver Broncos celebrates with his wife Nikki after their 26 to 16 win over the New England Patriots during the AFC Championship game at Sports Authority Field at Mile High on January 19, 2014 in Denver, Colorado.
(Jamie Squire/Getty Images)Derek Hagan and his wife Tiffany Hagan arrive at the Las Vegas premiere of the Warner Bros.
However, those ladies never ended up with the quarterback.