Tony Romo Dated Jessica Simpson & Carrie Underwood Before Finding Love
AP Photo/Jae. C. Hong

In terms of star status, there aren’t many athletes in Texas as famous as former Dallas Cowboys quarterback Tony Romo. The four-time Pro Bowl football player spent his entire 13-year NFL career in Dallas, where he won 78 games (but not a whole lot in the playoffs) and penciled himself in as one of the franchise’s greatest passers.

Romo retired in 2017, transitioned to sports broadcasting and now makes more money than many current NFL quarterbacks calling games in the booth for CBS Sports. It’s no surprise that someone of Romo’s stature ended up marrying a former beauty pageant queen who competed in Miss USA, but he also dated two bombshell country music stars.

Romo’s lack of success in the postseason is well-documented (remember the playoff fumble?), but he’s never had a problem scoring some of the most beautiful and famous celebrities. Let’s take a closer look at some of those relationships. Unsurprisingly, he ended up with a former Miss USA contestant like Tim Tebow and Christian McCaffrey.

Tony Romo & Jessica Simpson

AP Photo/Tony Gutierrez, file

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. They stirred the sports media world when pictures of them at a Cabo San Lucas resort surfaced before a pivotal playoff loss to the New York Giants.

Romo broke up with the singer and Dukes of Hazzard star in 2009 right before her 29th birthday. He reportedly broke up with her after she met John Mayer and suspected something happened between them. The kicker? He broke up with her via email.

“Tony didn’t believe that for a second. And within that second, he broke up with me right there. Two years, gone with an email,” she wrote in her book, according to TMZ.


I guess she found out those boots really were made for walking…right out of his life.

Tony Romo & Carrie Underwood

AP Photo/Jae. C. Hong

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Romo and Underwood dated briefly in 2007 before he and Simpson were an item.

The NBC Sunday Night Football theme song singer and former American Idol winner linked up with the zero-time Super Bowl winner and briefly dated before things turned sour.

“Point blank, [Romo] is about football,” she told Esquire of their relationship. “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.

“He hated so much that people thought that he was paying more attention to me and that was causing him to not do well.”

Crazy enough, Underwood went on to date Romo’s future brother-in-law in 2008. Hopefully she never took a Louisville Slugger to both headlights of either of their cars.

Who is Tony Romo’s Wife Candice Crawford?

Photo by Evan Agostini/Invision/AP

Candice Crawford was born on December 16, 1986, in Lubbock, Texas. She grew up near Dallas, though, and studied journalism at the University of Missouri. While in school, she won Miss Missouri USA and was one of 51 Miss USA contestants to fly out to Las Vegas for the 2008 Miss USA competition. The 21-year-old finished in the top 10.


Crawford traded swimsuits and gowns for an on-air career as a television personality afterward.

She worked in the Dallas-Fort Worth area as a sports reporter when she met Romo, and the two began going steady in 2009. Romo gave her an engagement ring and made her his fiancée the following year and they officially wedded in May 2011 at Arlington Hall in Dallas. Crawford then became Candice Romo.

Candice Romo didn’t need to marry Tony to boast stardom in her family. Her brother is actor Chace Crawford, who starred in the hit show Gossip Girl. He dated Carried Underwood in 2008 after Tony Romo did. Small world.

Candice and Tony have been happily married over the last decade and made plenty of public appearances. In 2010, they attended the TIME/CNN/People/Fortune White House Correspondents’ Association Dinner and MSNBC Afterparty at the Washington Hilton in Washington, D.C. Jay Leno performed and President Barack Obama and First Lady Michelle Obama attended.

They’re also big sports fans of their local teams. The Romos have showed face at Dallas Mavericks NBA games together. Romo himself played on the varsity basketball team at Burlington High School in Wisconsin. Candice appears to be pretty athletic herself:


How Many Kids Do They Have?

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I can't take him anywhere #cowboyschristmasparty


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Tony Romo and Candice Romo have three sons together and might not be done expanding their family.

Hawkins Crawford Romo was born in 2012, Rivers Romo in 2014 and they welcomed their third son, Jones McCoy Romo, in 2017. Romo said he loves being a dad.

“Oh, it’s super exciting!” he told Entertainment Tonight. “My third boy, you know, so, building my own basketball team here — getting close… I think the wife might want to stop at this point, but we’ll push her again in a year or two. Once they hold that baby, and that baby grows up a little bit, they want to hold that baby again, so… that’s just how wives are, and moms. I’d be all for trying for a little girl, but it’s really not my body, though.”

As the Romo family grows, one has to wonder: Could this be the next Manning family?

READ MORE: Scottie Pippen’s Ex-Wife Became Kim Kardashian’s Best Friend

Patrick has spent parts of the last four years covering University of Florida athletics and spent two seasons with Major League Baseball. He's a baseball junkie who spends his days defending Derek Jeter and the Miami Marlins. A recent Gator grad, Patrick currently resides in Gainesville, Florida.
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