Taylor Swift is hardly the first singer to date one of the most popular men in the NFL. Carrie Underwood made it cool in 2007, but a country legend had America’s quarterback on her arm in the early ’90s.

Underwood wasn’t far removed from American Idol when, in 2007, she started dating Tony Romo. He was the quarterback for the Dallas Cowboys (find him calling football games for CBS these days), and this relationship would be the first of two to put him front page of tabloids across America.

A romance with pop star Jessica Simpson followed. When the Cowboys would play away games, opposing fans would troll him and distract him.

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Why Did Tony Romo and Carrie Underwood Break Up?

Romowood are said to have started dating in 2006, and we can confirm it lasted through at least spring of 2007, because that’s when they walked the red carpet together at the ACM Awards. She’s never said why they split, but later she’d tell Esquire that he was more into football than her.

Asked if she’d ever write a song about him, Underwood shot back with, “No. I would never immortalize a guy that did me wrong. I would never give him that much credit.”

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Scroll down to learn who the other country star to date an NFL quarterback was. That relationship didn’t last, either — in fact, only three of the nine country singer and athlete romances we could find remain today. For Underwood, the second go-round with an athlete meant happily ever after.

However, the odds, it seems, may be stacked against Swift and Travis Kelce.

Romo would eventually marry Candice Crawford in 2011. Underwood is now married to former NHL player Mike Fisher.

DID CARRIE UNDERWOOD AND JESSICA SIMPSON REALLY FEUD OVER TONY ROMO?

Simpson and Underwood were singers in different spaces until Simpson chose to crossover into country music around 2007. And that wasn’t the only thing the two had in common during these years either. They were also connected by a guy they both dated. Being in close proximity to someone who used to date your current partner can be awkward, especially when the former flame publicly talks about still calling them. That’s the situation that Simpson found herself in when she was dating football player Tony Romo, ex-boyfriend to Underwood. But does this mean Simpson and Underwood had a feud? It’s debatable.

Carrie Underwood still called her ex, Tony Romo, who was then dating Jessica Simpson

Prior to Jessica Simpson and Tony Romo’s romance, Romo dated Carrie Underwood back in 2007, according to Livingly. This former relationship reportedly caused some tension between the two singers from the beginning, when Simpson started dating Romo in 2008. It ramped up when Underwood and Chace Crawford also broke up that year; Simpson was supposedly worried about what Underwood’s single status could mean.

This wasn’t helped by the fact that Underwood told Allure that she and Romo still talked on the phone. “[Jessica] is really upset that [Tony’s] still communicating with Carrie,” a source told Today, who said the NFL quarterback and the “Before He Cheats” singer would email and text even after Simpson “had specifically asked Tony to stop.” After Underwood made this public knowledge, Simpson responded on a San Francisco radio station, saying, “I don’t understand why she would say that … I respect Carrie, and I would never say anything like that.”

In response to the growing rift, Underwood told Elle she didn’t mean for anything she said to blow up. “It was just something that was said in passing … I would never mean to say anything to hurt anybody or stir up anything, because I’m just not about drama — at all,” Underwood said. “I might be mad too if somebody said my boyfriend was calling some other girl. So I can definitely see where she would be coming from.”

Jessica Simpson and Tony Romo dated for two years

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Despite the public-facing tension, the two singers always stayed true to their claims that there wasn’t a feud. Livingly reported that Jessica Simpson called the potential feud “media driven,” despite their different quotes. Apparently, that was the extent of the strain between them, and no bad blood happened behind closed doors. “I met her once and she seemed really nice so I don’t have a feud with anybody,” Carrie Underwood told People in 2008. She also said that she typically stays friends with exes, so it didn’t seem malicious or weird for her to keep in contact with Tony Romo.

Simpson’s relationship with Romo lasted until 2009, about two years. Around the time of the Underwood “feud,” a source told Today that Simpson had a tendency to be jealous of Romo with any women. “It took a toll on their relationship,” the insider said. Regardless, they had a sweet start to their romance, with Simpson watching a game of his where he said he had a crush on the singer. She, unfortunately, went on to be known as a jinx when she would go to his games and he started losing. But he told Vanity Fair that he appreciated Simpson and her support. “It’s nice to have someone to come home to and try to make you feel better.” But their relationship ended when, reportedly, John Mayer (who Simpson dated in 2006) started meddling back in her life.