Despite dating for a year and a half, Jessica Simpson and Tony Romo never married. Their romance began in November 2007, during Jessica’s ongoing separation from Nick Lachey.
First Date and Early Romance
Jessica Simpson and Tony Romo met through a mutual connection. Her father, Joe Simpson, was a fan of Tony Romo and had a friendship with him. Joe Simpson introduced Tony Romo to his daughter Jessica during a football game in November 2007.
“The cute story is that my family and I were watching a Cowboys game,” Jessica explained in an interview with Glamour in April 2008.
“I was going through my divorce and — Tony would die if I told you this — but (on television, there was a story) about him. They said his celebrity dream crush was Jessica Simpson.”
Meeting for the first time a year and a half later, they kissed on their first date.
“The fact that this guy, on our first date, in the first 10 minutes of dinner, wanted to lean over the table and say, ‘This is my girl and I want to kiss her’ — our first kiss in front of everybody — was awesome.”
A very intoxicated Jessica Simpson is helped into her car by her boyfriend Tony Romo after seeing ’80s metal/hard rock tribute band Metal Skool perform at the Key Club on the Sunset Strip in Hollywood on January 28, 2008 (Credit: WENN)
Breakup and Moving On
She broke up with Tony Romo, a quarterback for the Dallas Cowboys, on July 9, 2009, just one day before her 29th birthday.
“She is heartbroken,” a source told People after the breakup. She loves Tony, but it’s been difficult lately. He’s busy with his career, and she’s getting ready to shoot her show (The Price of Beauty). They decided to part ways.”
Tony Romo, an American football television analyst and retired quarterback with a net worth of $70 million as of 2024, married American journalist Candice Crawford on May 28, 2011, at Arlington Hall in Dallas.
Dallas Cowboys quarterback Tony Romo tied the knot with pageant queen and TV reporter Candice Crawford at Arlington Hall, a historic mansion on the grounds of Dallas’ Lee Park in Dallas, Texas, on May 28, 2011 (Credit: WENN)
They started dating in the summer of 2009, shortly after his relationship with Jessica Simpson ended. Meeting when she interviewed him as part of her internship, they have three sons: Hawkins Crawford Romo was born on April 9, 2012, followed by Rivers Romo on March 18, 2014, and Jones McCoy Romo on August 23, 2017.
According to The Dallas Morning News, Tony Romo signed a record-setting deal with CBS in February 2020 worth approximately $180 million over ten years. This contract makes Romo one of the highest-paid sports broadcasters, earning around $17 to $18 million per year.
Reporter Candice Crawford (L) and professional football player Tony Romo attend the 50th Academy Of Country Music Awards at AT&T Stadium on April 19, 2015, in Arlington, Texas (Credit: WENN)
Candice Crawford: Career and Family
The 2008 Miss Missouri USA and a former journalist for Dallas television station KDAF, Candice is the younger sister of actor Chace Crawford, who played Nate Archibald on The CW’s teen drama series Gossip Girl.
Before dating Jessica Simpson and Candice Crawford, Tony Romo also dated Carrie Underwood, the country music star, from around 2006 to 2007.
Candice Crawford and her older brother Chace Crawford attend The CW Network premiere of “Gossip Girl” at Tenjune on September 18, 2007, in New York City (Credit: WENN)
Jessica Simpson at the Mockingjay Premiere
In November 2014, Jessica Simpson joined Jennifer Lawrence for the “The Hunger Games: Mockingjay — Part 1” premiere at Nokia Theatre L.A. Live in Los Angeles.
Jessica Simpson wears her blonde hair down at the premiere of “The Hunger Games: Mockingjay — Part 1” held at Nokia Theatre L.A. Live in Los Angeles on November 17, 2014 (Credit: WENN)
The then 34-year-old entertainer sported a gold vintage one-shoulder dress and accessorized with Neil Lane jewelry. She carried a Ferragamo clutch and completed the outfit with a stunning pair of Prada heels.
Jessica Simpson shows off her legs in a vintage gold dress (Credit: WENN)
Do you agree that this dress looked unflattering on Jessica Simpson?
Jessica Simpson kisses her husband, Eric Johnson, at the premiere of “The Hunger Games: Mockingjay — Part 1” (Credit: WENN)
The all-gold look was just too much, and the bodice of the dress could have used some more support.
Jessica Simpson accessorizes with Neil Lane jewelry (Credit: WENN)
Jessica Simpson’s feet in Prada sandals (Credit: WENN)
Jessica Simpson shows off her toes in gold metallic heels (Credit: WENN)