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ilookedintoit · 10 hours

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Carrie & Tony & Jessica & John

The recent media obsession with Taylor Swift and Travis Kelce - and the proceeding debate about whether there was too much focus on Taylor attending NFL games - reminded me of the attention, mostly negative, that was given to both Carrie Underwood and Jessica Simpson 16-17 years ago when they took turns dating another NFL player, Dallas Cowboys quarterback Tony Romo.

The timeline of Tony & Carrie and Tony & Jessica was not at all clean and linear, and it led to some interesting interactions and comments in the media as these relationships evolved.

Adding to the drama and making it as messy as possible was John Mayer's insistence on remaining a part of Jessica's love life, before and during her relationship with Tony.

I wanted to delve into this classic mid-aughts love quadrangle and figure out the timeline of how it all went down.

August 2006

TMZ reports that Jessica Simpson is dating John Mayer, less than a year after her divorce from Nick Lachey of 98 Degrees.

Jessica Simpson's album "A Public Affair" isn't the only thing coming out today. Us Weekly is reporting that she and Grammy winning singer/songwriter John Mayer are an item, but sources say Simpson wants to "keep it private." Um...sure! If reports are true, this would be her first relationship since breaking up with ex-husband Nick Lachey.

Jessica confirms in her 2020 memoir, "Open Book," that she had begun secretly dating John several months before the news leaked - from someone close to her:

The week of my release someone from my team broke the story to the tabloids. Coming just a week after my album came out, it looked like a full-on, amateur stunt orchestrated to sell both our albums. I fired the person. John was worried he seemed in on it and felt that his artistic integrity was in jeopardy. I was in New York and he exploded on me, breaking up with me over an email. On August 31, he posted the cover of Public Enemy's "Don't Believe the Hype" on his blog as a response to the media. I was humiliated and thought he was out of my life for good. He wasn't.

September 2006

Jessica and John get back together. People Magazine features a cover story about their relationship.

November 2006

Tony Romo is the newly-named starter for the Dallas Cowboys, with no prior celebrity relationships under his belt. His fame is just starting to rise with his new role on the NFL's most high-profile team.

In mid-November, one media outlet called The Sporting News alleges that Tony is now dating Jessica. This is a possible connection because Jessica is a Dallas native who still visits Texas often.

Later in the month this rumor is bolstered when Sports Illustrated reports that Tony was seen having dinner with Jessica and her manager-father Joe Simpson in Los Angeles, and that Tony provided Joe Simpson with tickets to the November 12 Dallas Cowboys game.

The buzz begins being reflected in fan interest at the games with signs like this:

On November 23, Carrie Underwood - who has become a huge country star after winning American Idol in 2005 - performs at the Dallas Cowboys halftime show on Thanksgiving, at the same time that the Tony Romo-Jessica Simpson rumors are in full swing.

On November 29, Tony is asked about the speculation and denies that he is dating Jessica.

"Jessica and I are not dating, so no one has to write about that. Very funny, though. But anyhow, I guess there are worse things." (Source: Fort Worth Star Telegram)

He is apparently telling the truth; Jessica does not mention dating Tony during 2006 at all in her book. She was still fully entangled with John during this time, with him dumping her again by late November 2006:

Honestly he did it so many times I lost track. Always in an email... He'd dump me, then come back saying he had discovered he loved me after all.

December 2006

On December 1, Tony is interviewed by FSN Pro Football Preview and is asked which “tabloid starlet” he would like to date.

“I don’t know that I’d choose one. But one who I think is cute and does it the right way is Carrie Underwood. We’ll watch her. But I’m never going to mention anyone else’s name ever again. This is the last one…”

On December 3, both Jessica and Carrie are slated performers at the Kennedy Center Honors tribute to Dolly Parton.

Jessica states in her memoir that even though John had recently broken up with her, the night before the event he sends her song lyrics to the Aerosmith song, "Angel." This causes her to go into a tailspin wondering what was going on with him.

She began drinking backstage prior to the show, she said, and then John called her right before she was supposed to perform, which turned into an ugly conversation.

When she finally gets on stage to sing, she botches the words to "9 to 5" and has to stop singing. Her part is subsequently cut from the final broadcast.

Later, as the night’s performers, including country stars Carrie Underwood, Reba McEntire, and Kenny Rogers gathered onstage, Jessica appeared to have been crying. (Source: The San Francisco Examiner)

She and Carrie are not seen or photographed together during the evening, but you can see them entering from opposite ends of the stage at the end of the event.

A December 20 report seems to confirm that Tony and Carrie are really seeing each other after Tony allegedly says as much to a reporter from his college town's newspaper.

OK, talk about Tony Romo and Jessica Simpson apparently was just fabricated rumor. But believe that the former Eastern Illionis quarterback suddenly nationally known star for the nation’s team is seeing former American Idol winning singer Carrie Underwood. “That one is true,” Romo said. (Source: Journal Gazette)

On Christmas Day 2006, Carrie attends the Dallas Cowboys game. She is pictured hugging Tony on the sideline before the game and then seen watching the action from the owner's suite. The Cowboys lose badly, which the media cannot help mentioning as they discuss Carrie's appearance at the game.

Yards Per Carrie? Apparently the best way to impress a pop princess is to become the starting quarterback for the Dallas Cowboys. When being linked to Jessica Simpson got old, Tony Romo turned his attention to former “American Idol” Carrie Underwood. During the telecast before the first Monday night game, it didn’t take NBC long to find Underwood, in part because she somehow secured a field pass and was shown talking to Romo and another young woman. With end zone seats scarce, Underwood watched from Jerry Jones’ luxury suite as Romo and the ‘Boys got clawed by the Philadelphia Eagles, 23-7. NBC’s exclusive Carrie Cam provided memorable shots during the first half. No one asked Romo about his Christmas date after the game because the timing seemed wrong. When asked earlier this month about rumors that he was dating the “American Idol” winner, the former Eastern Illinois quarterback was quoted in the Journal Gazette & Times-Courier, “That one is true.” (Source: Fort Worth Star Telegram)

Famed sportscaster John Madden echoes a sentiment quick to be dispersed throughout the sports media landscape, blaming Carrie's presence for Tony's bad performance:

During Monday’s NBC telecast, John Madden said Romo might have been distracted because Underwood visited Romo on the field two hours before the game and gave him a hug. He said, “If I were in a relationship, I would feel bad for the girl because I wouldn’t have time for her. It’s football season."

January 2007

A new report early in the year claims everything about Tony and Jessica dating was just made up for some game day tickets.

In unbelievably tacky fake hookup news, recent reports that Jessica Simpson is dating Dallas Cowboys quarterback Tony Romo are false. And who started the rumors? Her own father, Joe Simpson. The New York Post reports that Papa Simpson let Romo name-drop his daughter in exchange for game tickets, and the two supposed lovebirds have never even met. In reality, Romo is dating American Idol finalist Carrie Underwood, and Simpson was just spotted again with John Mayer. (Source: Hartford Courant)

The Cowboys lose their wildcard playoff game on January 6 after Tony botches the hold for a field goal that would have let Dallas take the lead near the end of the game. Criticism for his end-of-season play comes to a fever pitch. Carrie is not at the game.

On January 21, Carrie says the rumors about her and Tony were always overblown.

"The first time I ever met him was on Christmas, right there on the field. Everybody was like, 'Ooh, they are together.' And then I was blamed for Dallas not winning that game... He is a very nice guy and I've talked to him a few times, but we are very much not together." An Illinois newspaper had originally reported that Tony admitted the two were dating and Carrie struck back saying, "That was one person from one local newspaper that said that, so whether or not..." "I've read 'sources said' we met on Thanksgiving. I had no clue who he was at that time. He is probably getting a little tired of that one (the false rumor he was dating Jessica Simpson) and now he's probably tired of this one..." (Source)

Meanwhile, Jessica and John are back together again, and publicly. They are seen out together on January 23 in Miami.

Jessica: He said a lot of our breakups were about me drinking and not being present for him, which was not, I would only find out much later, the full truth. But I took him at his word about his motivations, and that's why I always went back. It was my fault, and if he forgave me, that was all that mattered. (Source: Open Book)

February 2007

During Super Bowl week, Tony also denies a romance with Carrie:

“We’re friends," Romo said. "She's a very nice, sweet girl, I care for her, and whoever ends up with her will be a very lucky guy." (Source: Chicago Tribune)

Unconfirmed reports claim Carrie is "dating British singer Oliver Trevena, after dumping football hunk Tony Romo." I am not sure if she ever really dated that person.

Meanwhile, Jessica and John attend a Grammys party together on February 11.

We went to Sony’s Grammy afterparty together, and I was so happy he posed for pictures with me, because Grammy night is like the prom in our industry. He was nominated for five awards and won two that night. He broke up with me that night at the Four Seasons in Beverly Hills. I can’t even recall why. I just remember knocking on his hotel room door and begging until he finally took me back in the middle of the night. (Source: Open Book)

Despite this tumultuous dynamic, John and Jessica will be seen out together on several more occasions throughout the spring, including at Madison Square Garden later in February, in New York City in March, visiting Australia in April, and at the MET Gala in May.

April 2007

In the April 2007 issue of Cosmopolitan, Carrie denies that she is dating Tony and says her last serious relationship was her college boyfriend, Drake.

But on April 22, Carrie is seen celebrating Tony's birthday with him at a party in Dallas.

American Idol winner Carrie Underwood and Cowboys quarterback Tony Romo insist they’re just friends, but they continue to send mixed signals. A spy for People spotted them at Dallas’ Ghostbar on Sunday for Romo’s 27th birthday bash, joined by his teammates. The mag’s Web site reports that the pair “looked very cozy” and that their “arms were around each other all night” in the deejay booth. Underwood spokesman Jessie Schmidt acknowledged that the two have been spending time together but are “definitely not boyfriend/girlfriend. It’s very casual at this point." (Source: Fort Worth Star Telegram)

Heavily watermarked pictures of Carrie and Tony partying together were posted here.

May 2007

On May 15, Tony escorts Carrie to the ACM Awards. A notable moment commented on in the media is when she wins an award and hands him her purse to hold while she goes up on stage to accept.

Quizzed about her date at last night's country celebration, the former American Idol winner gushed, "We're really good friends and we hang out and we support each other and everything that we do and it's great to have somebody here who's got your back." Meanwhile, Romo confessed, "We're just getting to know each other a little better and we'll see where everything goes, but it's just nice to have somebody at the end of the day to talk to who is going through similar things. "She's got a great personality, so she's really easy to talk to... (and) she loves to talk on the phone." Underwood revealed backstage that her awards show performance would be the first time Romo has seen his sweetheart play live. (Source)

June 2007

A tabloid report claims Tony has told Carrie that he wants to take a break so he can focus on the upcoming football season.

The season begins in September and ends in January. “Carrie thought that they were moving to a more committed relationship,” a source told the tabloid. Romo asked Underwood to give him space for his career once before, and she did this, but this time, the request has hit a sour note with her, says the source, who added, “Carrie wants a firm commitment.” (Source: MSNBC.com)

September 2007

Carrie's album "Carnival Ride" is released and she tells an interviewer that she and Tony have always been friends and weren't really dating.

Also in September, reports come out that Jessica is planning to make a country album. In response to that news, this little comparison chart is printed in the Chicago Tribune:

By September, Jessica and John are broken up again, and this time they remain apart long enough for her to start thinking about dating someone new. John is spotted out with actress Minka Kelly in late September, and he will date her for the next few months.

October 2007

In the October 26, 2007, issue of Entertainment Weekly, Carrie tells the reporter that she and Tony never got the chance to become a real couple and seemingly confirms that things didn't work out for them because of football and the negative attention:

“At one point it seemed like that’s where it was headed, but point blank, he is about football. 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 he was paying more attention to me and it was causing him not to do well.”

That same week, Carrie is linked to actor Chace Crawford with the two of them being spotted out together in New York City. Earlier in October, Tony is linked to actress Sophia Bush, but that's denied by sources. He is then seen partying with celebrities including Britney Spears on Halloween.

November 2007

Carrie covers Seventeen Magazine and addresses the Tony relationship again:

"We're very good friends, and I talk to him pretty much every day, whether it's a text or whatever," she says. "But we were never, like, dating. We hang out. We like doing the same things, and we come from similar backgrounds, and we both stumbled into big fame real fast. So we understand where each other is coming from. It's just the wrong time for both of us. In a different world, we might have dated. But not in this one right now." (Source)

While the timing might not have been right for Tony and Carrie, it apparently becomes right for Tony and Jessica, finally. At the end of November, Tony is linked to Jessica for real this time, a year after the initial rumors about them began.

Hours after guiding his Dallas Cowboys to a Thanksgiving Day win over the New York Jets, Tony Romo grabbed dinner with Jessica Simpson in Dallas. Romo, 27, arrived at the Dragonfly restaurant inside the swank Hotel ZaZa at around 7 p.m. Thursday, shortly after Simpson, also 27. They settled into a corner table with about 25 friends and family. (Source)

Jessica states in her book that their relationship began after she saw Tony say on TV that she was his dream girl. Knowing that he had been friendly with her father, she asked her dad to reach out to him.

We went public quickly, which was also new for me. It was easy. He had no interest in drama. He said the Lord’s Prayer every night before bed. A solid person who was the kind of guy that, as a kid, I imagined marrying.

December 2007

Jessica attends the Cowboys game against the Eagles on December 16, 2007, just as Carrie had done almost a year before. Tony's performance is also similar to that of his performance when Carrie attended.

From Jessica's memoir:

I proudly wore a pink version of Tony's jersey with his number nine on the front, and there I was, cheering on my guy. Annnd he proceeded to play the worst game of his career. ... "Send Jessica home!" the chant began. "Send Jessica home!"

"Jinx" was the word everyone used. The media was cruel, and even Tony's teammate Terrell Owens talked about me to the press. "Right now, Jessica Simpson is not a fan favorite," he said, "in this locker room or in Texas Stadium." He also helpfully added that the last time Tony played close to this bad was the year before, when he had dated Carrie Underwood.

The nickname "Yoko Romo" is quickly assigned to Jessica and the media unleashes some pretty mean and unfair commentary.

January 2008

Tony is spotted on vacation in Cabo with Jessica a week before the Cowboys lose to the New York Giants in the playoffs.

The media narrative becomes that the vacation made Tony unfocused for the game, and it leads to more backlash against Jessica who apparently forced him to go, or something!

Jessica Simpson can vacation with boyfriend Tony Romo anywhere she wants now. NFL quarterback Romo has lots of free time, now that the New York Giants knocked him and the Dallas Cowboys into the offseason Sunday. But he may want to keep Simpson away from Dallas, where fans are blaming her for the Giants 21-17 victory in Sunday's big playoff showdown. (CBS)

John for some reason decides he needs to pipe up and defend his ex-girlfriend on his blog:

“Dear Dallas and Surrounding Areas, This isn’t a sports blog, and it isn’t a publicity stunt. (but have at me if it feels right.) This is about doing what I think is right as a person, in this case speaking my mind. I have never known anyone to have more pride in their home state and their upbringing in it than Jessica Simpson has in Texas. I don’t really follow sports, but I have played some of my biggest and best concerts in your state, and having witnessed how dynamic the spirit there is, I’m betting emotions are running high right about now. All witty barbs, blogs, and fashion policing aside, that girl loves Texas more than you know. It’s one of her most defining traits as a person. So please don’t try and take that away from her. (You probably wouldn’t be able to, but it’s less work for all involved.) I just thought it would mean something coming from the guy who has the absolute least to gain from this. And if I’m out of line in having written it, too bad. I can spare a Wednesday’s worth of bad press if it means sticking up for a good soul. JM”

"The absolute least to gain from this" ... except maybe trying to keep an emotional hook in your ex-girlfriend's heart.

June 2008

While it is not addressed in Jessica's book, some media reports claim that Tony and Jessica break up but get back together during the summer of 2008. Some reports blame Jessica's "meddling" father, while at least one tabloid claims she's also jealous of Carrie.

“(Jessica) is really upset that (Tony’s) still communicating with Carrie,” the source said. In fact, the insider revealed that the Dallas Cowboy quarterback frequently contacts the country-music star via e-mail and text messages even though he knows it bothers Jess. “She had specifically asked Tony to stop,” the insider added.

On June 13, 2008, Jessica is pictured wearing a Real Girls Eat Meat shirt. Tabloids like OK Magazine immediately question if this is a dig at Carrie because Carrie has been very outspoken about being a vegetarian. OK Magazine claims:

"Jess is sick of hearing about how Tony still has feelings for Carrie," says the insider. "She's obviously trying to poke fun at her rival and let her know who really has Tony's heart."

August 2008

Adding fuel to the simmering fire, Carrie says in the September issue of Allure Magazine that Tony still calls her.

"The phone will ring and it'll be him, and I'll maybe not answer," says the singer, 25, of the Dallas Cowboys quarterback, adding that the relationship wasn't serious. "We were both small town people doing very big things, and we relied on each other, dealing with fame."

Soon after, Jessica is asked about this quote during a radio interview, and she says it's not true. She also says she and Tony "laughed" at the statement, and denies that her shirt was a dig at Carrie.

“Tony and I both laughed at that,” Jessica told the Woody and Jim show. “Yeah, we got a chuckle out of it.” The actress-singer then joked that she even “looked at his call log” just to make sure, before adding, “I’m kidding! I’m not that girl!” In the September issue of Allure magazine, Carrie implied that her ex-boyfriend was just a phone call away, saying, “The phone will ring and it'll be (Tony), and I'll maybe not answer.” But Jessica insists it’s “definitely” not true, and “if Tony wanted to call her or be with her, he would.” While she was on the subject of dispelling Carrie-related rumors, Jessica cleared up the controversy about her “Real Girls Eat Meat” shirt. “I wore it because I thought it was funny,” she said. “I don’t know what Carrie eats. I didn’t know she only eats vegetables.” (Source)

September 2008

Fans of the Cleveland Browns use both Jessica and Carrie's likenesses to taunt Tony during a game versus the Cowboys.

October 2008

John, who has somewhat been in a relationship with Jennifer Aniston since May 2008, shows up to Jessica's parents' Halloween party, which she is attending with Tony.

If John texted or emailed, I would hold up my phone and tell Tony immediately. He knew the hold John had over me, and it was like telling your sponsor when you're triggered. He'd seen how I reacted when John randomly showed up at my parents' Halloween party in Encino. I had no idea he was coming and was shocked. ... Not how you want to run into your ex with your current boyfriend standing right next to you. John routinely used his friendship with Ashlee's then-husband, Pete Wentz, as an excuse to stay in the Simpson family orbit. My parents knew what he had done to me, but John was always so charming. (Source: Open Book)

November 2008

Carrie tries to smooth things over from` her previous comments about Tony calling her, and says she did that interview a long time before it ever came out.

“See, this is always a tricky thing,” Underwood answers. “I don’t think people realize that when you do an interview, the magazine comes out six months later. It was just something that was said in passing, and I would never mean to say anything to hurt anybody or to stir up anything, because I’m just not about drama. At all. I might be mad too,” Underwood adds, “if somebody said my boyfriend was calling some other girl. So I can definitely see where she would be coming from. But I haven’t talked to him since, like, May.” (Source)

But Tony was dating Jessica in May, so this possibly could lend credence to the June 2008 reports that Jessica was upset about him communicating with Carrie — despite Jessica's denials.

May 2009

Everyone seems to move on with their lives, with the exception of John. After ending his nine-month relationship with Jennifer Aniston, he has set his sights back on Jessica.

According to her memoir, John remains friends with Jessica's parents, which keeps him connected to her life. It is interesting, and strange, to note that it is Jessica's father's connection to Tony that gets them together in the first place, and it is her parents' connection to John that keeps him in her orbit.

He told them he had read my Vanity Fair cover story that came out in May. My parents told me he went on and on about it. He emailed me about it, too, telling me how amazing it was and that he loved me and wanted me back. (Source: Open Book)

June 2009

John's pursuit of Jessica intensifies, according to her memoir.

As we got closer and closer to July and my birthday, he ramped up his wooing of my family. He told them in no uncertain terms that he had changed, and he could tell I had changed, too. "I need her back," he said. "I'm in love with her."

July 2009

Jessica and Tony are seen out on July 1 at a golfing event with Tiger Woods, but they will break up only eight days later.

Ironically, after all the hullabaloo in the press about Tony maybe calling Carrie, it is Jessica and John's communicaton that leads to the demise of their relationship.

The day before Jessica's birthday, on July 9, Tony breaks up with Jessica.

Radar Online orginally reported this story back in 2009:

Dumping someone before their birthday weekend seems especially harsh, but a source tells RadarOnline.com exclusively that Tony Romo had good reason for calling it quits with Jessica Simpson the night before her Barbie and Ken-themed bash. He found messages from her ex John Mayer! Flying into Los Angeles on Thursday, Romo quickly made up for lost time with Simpson but their reunion quickly took a turn for the worse. “They were hanging out and he picked up her phone and she got defensive about it,” the source revealed. “Tony found messages from John and went ballistic.” While the couple has had their fair share of rocky patches during their relationship, the idea of Simpson possibly cheating with Mayer was the straw that broke the camel’s back: “Tony dumped her right then. He walked out and that was it.” (Source)

And in her 2020 memoir, Jessica confirmed that this was the true story.

Simpson claims that her father brought Mayer over to their home in Los Angeles when she was in town. “By a fire in the backyard, he stood and told all of us that he loved me and that we could all trust him to be a good man. I told him I would always love him, but I was with Tony,” she said. “But I didn’t tell Tony. I broke my own rule of full disclosure about any contact, even accidental, with John.” Soon after, Romo saw an email from Mayer on Simpson’s phone and suspected they were seeing each other behind his back. “I hadn’t cheated on Tony at all, but I could not lie and say I hadn’t even seen him,” she said. “And within that second, he broke up with me right there. Two years, gone with an email.”

After clearing his head, Jessica says in her memoir that Tony realized she was telling the truth and had not cheated. But, she decided that breaking up was the right thing to do:

When he said he wanted me back, I was honest with him. “No, you did what I needed to do,” I said. “Thank you.” “This is really over?” “You broke up with me, so yes,” I said. “It’s over.”

Jessica states in her book that she did end up reconciling with John privately after her breakup with Tony, for a brief and regrettable time.

September 2009

Media outlets report that Tony is dating Candice Crawford. Funnily enough, Candice is the sister of Chace Crawford, who briefly dated Carrie in 2007. At the time, Candice was host of the Cowboys' weekend sports show, Special Edition, which is presumably connected to how she met Tony.

December 2009

Carrie gets in one last word about Tony, when she's asked if he's the inspiration for her song "Cowboy Casanova."

The country crooner recently told Esquire magazine that her hit song, “Cowboy Casanova,” was definitely not about the NFL quarterback. “No. I would never immortalize a guy that did me wrong,” Underwood told the men’s magazine. “I would never give him that much credit.” (Source)

This same month, Carrie gets engaged to hockey player Mike Fisher, who she has been dating since 2008.

February 2010

Jessica states in her memoir that she remained connected to John until his infamous February 2010 interview with Playboy. His comments about her and other women are the turning point for Jessica.

“That girl is like crack cocaine to me,” Mayer said of Simpson. “Sexually it was crazy. That’s all I’ll say. It was like napalm, sexual napalm. Did you ever say, ‘I want to quit my life and just f—ing snort you? If you charged me $10,000 to f–k you, I would start selling all my s–t just to keep f—ing you.'”

Jessica speaks on her reaction in her memoir:

I didn't accept his apology. I deleted all his contact information from my phone. I was done with this man in a way I never thought was possible. When he reached out to me, I changed my number and changed my email. Delete.

May 2010

Jessica begins dating former NFL player, Eric Johnson.

July 2010

Carrie marries Mike Fisher.

November 2010

Jessica announces her engagement to Eric. They will marry in 2014.

December 2010

Tony and Candice get engaged. They marry in 2011.

Where are they now?

Tony, Carrie, and Jessica are still married to their spouses as of 2024.

Jessica released her memoir, "Open Book" in 2020, and openly discussed her struggles with alcohol abuse and getting sober in 2017.

John went on to have another off-and-on celebrity relationship with Katy Perry from 2012-2015 and was immortalized as a terrible boyfriend who took advantage of a 19-year-old in the Taylor Swift song "Dear John." He has never gotten married.

#jessica simpson #carrie underwood #Tony romo #john mayer

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