Tony Romo-Jessica Simpson dating timeline: Revisiting the NFL’s love fixation before Taylor Swift-Travis Kelce

For every great figure in history, there is a predecessor that has paved the path for them. Before Travis Kelce, there was Rob Gronkowski, Antonio Gates, and Tony Gonzalez. Before Taylor Swift, there was Beyonce, Madonna, and Mariah Carey. 

The point? It’s very rare nowadays for there to be a true “first” in society. That’s no different when it comes to celebrity power couples in the NFL. 

The relationship between Kelce and Swift has been a focal point for the 2023 NFL season, and rightfully so. When the world’s most popular singer links up with one of the most famous players in the NFL, it’s sure to bring in eyes. However, this isn’t the first time the NFL and pop culture worlds have crossed over romantically, and it most certainly will not be the last.

Before Swift and Kelce, there was a QB-pop star couple that was thrust into the spotlight — Tony Romo and Jessica Simpson. The former Cowboys’ quarterback and current CBS broadcaster was one half of the celebrity couple that dominated the late 2000s. 

Let’s take a walk down memory lane and revisit Romo and Simpson’s relationship. 

MORE TAYLOR SWIFT: Travis Kelce dating timeline | Will she go to Super Bowl 58?

Tony Romo-Jessica Simpson dating timeline

November 2007: Before the pair ever met, Romo expressed that he had a crush on Simpson. According to the singer, she was watching an NFL game at home with her family when Romo told reporters that she was his dream celebrity crush. 

“My family was like, ‘Did you just hear that?’” Simpson said in 2008 to Glamour. “His picture came up, and I’m like, ‘He’s really cute.’ Then I heard [that I was his crush], and I’m like, ‘Oh my gosh!’”

A mutual friend introduced Romo to Simpson’s father, Joe, and soon the duo met and hit it off right away. Romo even kissed her on the first date, wasting no time getting acquainted with his crush. Before the month was over, the two spent Thanksgiving together. 

December 2007: After about a month of dating, Simpson was attending Romo’s games. Her first appearance came during a 10-6 loss to the Eagles in Week 15, but Romo was winning off the field, as Simpson sported a pink Dallas jersey with his name on the back. 

April 2008: The two were going strong through the spring of 2008. In April, the pair were together to celebrate Romo’s birthday. It was at this event that the frosting fight occurred, with pictures of Romo and Simpson decorating each other’s faces with icing from the birthday cake in a flirtatious fashion. 

May 2008: This is where things began to get rocky between the two. Rumors began to swirl in May that the couple could be heading for a split. Part of that had to do with the fact that Simpson was reportedly “devastated” to find out her ex-boyfriend, John Mayer, had started seeing actress Jennifer Aniston. 

Simpson’s representatives denied any claim of a breakup, and Romo later attended Simpson’s sister’s wedding in the same month. 

February 2009: The breakup rumors died down in the summer of 2008, as the couple continued strong throughout the rest of the year. In February of 2009, Simpson took the chance to truly showcase her love for Romo, writing and dedicating a song to him, titled, “You’re My Sunday.”

MORE: How much money does Tony Romo make?

July 2009: The day before Simpson’s 29th birthday, Romo reportedly broke up with her. At first, Romo received backlash for the ill timing of his decision, leaving Simpson “heartbroken.”

“She loves Tony,” a source told Page Six. “But it’s been difficult lately. He’s busy with his career and she’s getting ready to shoot her show. They decided to part ways.”

Simpson later revealed that while their respective careers certainly played a part in the split, it was actually Mayer who was the core reason for the breakup. While Simpson and Mayer’s relationship had ended before Romo came into the picture, the singer/actress reportedly was still seeing and communicating with Mayer now and then, which rightfully irked the former quarterback. 

“If John texted or emailed, I would hold up my phone and tell Tony immediately,” Simpson said in her memoir, “Open Book.” “He knew the hold John had over me, and it was like telling your sponsor when you’re triggered.

“I hadn’t cheated on Tony at all, but I could not lie and say I hadn’t even seen him. And within that second, he broke up with me right there. Two years, gone with an email.”

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