15 Things Fans Didn't Know About Tony Romo And Jessica Simpson's Messy Break Up

Jessica Simpson (the former pop sensation) and Tony Romo’s very public relationship was most definitely the talk of the town for quite a few years. Tabloid TV and newspapers were abuzz with any tidbit of news they could dig up on the couple. As it turned out, they dug up quite a bit and their faces adorned the covers of many tabloid magazines a few years back. People still talk about the couple and their messy breakup until this day. Very much like Brad and Jennifer, these two had controversy and rumours following them around for all their days together and afterward.

RELATED: Photos Of Jessica Simpson That Would Drive Her Exes Crazy

Simpson, a singer who signed her first record deal with Columbia at the tender age of sixteen and Romo, a star football player with the Dallas Cowboys, were no strangers to the public eye, but their relationship garnered so much attention, we’re sure even they were left frustrated and wanting to disappear from the public eye.

Well, ending their relationship only caused the press to seek them out even more, and still today fans and millions of press junkies are still wondering about how their end actually came about. The old rumour mill is indeed turning at full speed on this one, ladies and gents and we at The Sportster are on top of it. Here are 15 things you may not have known about their messy breakup.

15 Her Father Was Too Meddlesome

via etonline.com

A source close to the couple stated that Jessica’s father and manager was way too controlling and meddled way too often, not only in her professional life, but he also stuck his nose in their relationship. The source also claims that Tony had had enough and brought this to the attention of his girlfriend, but to no avail… she was extremely reluctant to do anything about her father’s constant involvement in her life.

Many close to the couple believe that this was one of the main reasons why the couple split, or rather what drove Romo to end the relationship. He couldn’t imagine Joe as his father in law and well, we can’t blame him there. Joe Simpson is famous for being a control freak when it comes to his daughter Jessica.

14 Jessica Struggled With Her Appearance

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Body image is important to anyone, let alone Hollywood celebs. People can obsess over their bodies and most times it can even become a serious problem. For Hollywood celebs, their lives are out in the open and they can’t hide the fact that they’ve gained a few pounds, let alone any other problems that may come to the surface.

It was very hard for Jessica Simpson, as it still is, as the press love to shine the light on the fact that she’s heavier than she apparently should be. At the time of their relationship, many speculated if the weight gain was a problem for Tony, and some even wondered if that was the shallow reason he had left her. Yet, as it turns out, Simpson has gone on record as saying that Tony supported her immensely and was there for her, no matter what.

13 They Didn't Have Time For Each Other

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For Jessica, her dreams of singing and recording albums had indeed come to fruition, and if it wasn’t for her father pushing her to do more and perform more, then it was her very own drive for success that pushed her forward.

As For Tony, he was a definitely driven football star with a colourful career to his name. He was driven to succeed more if not equally to his partner. He still is very driven to this day, as he is an on-air analyst for CBS Sports. Friends and sources close to the couple stated that they simply didn’t have much time together, and the time they did have together was problematic … if not for the press following them around, then for her father.

12 Rumours Of Cheating On His Part

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Rumours can sometimes be quite a bit to digest, but this one comes from sources quite close to the former couple. As it turned out, there was a party being held at Jessica’s home when they were together. Rumours that Romo was hitting on girls and taking them upstairs for a little “private time” ran rampant.

Sources close to the ex-football star who were present at the party have gone on record to say that yes, there were a few after parties held at Jessica’s house, and there were indeed a lot of women there, but they claim that Romo was the perfect gentlemen and nothing ever happened. But rumours being what they are, many still believe that he did in fact cheat on Jessica at such times.

11 That Was The Lowest Point of Her Career

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Her decline in success came with her fifth studio album, A Public Affair. It performed terribly on the charts and in the media and it marks the start of her bad musical publicity. It was also at this time that she tried her hand in film, but it was hard for her to find an appropriate audience in film form. She starred in Employee of The Month with Dax Shepard and it received abysmal reviews. Other films include, The Dukes of Hazzard and Blonde Ambition.

It was then stated in a press release by her father Joe, that Jessica was planning on “going country” for her next album. Well, in 2008, Do You Know was released and flopped considerably and received terrible reviews. Her mad scramble to re-attain her earlier success only led further to her fall. It was only a little over a year later that her relationship with Romo ended. Many have wondered if the stress over her dimming celebrity star was having an effect on their relationship.

10 She Celebrated Her Birthday Alone

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Simpson spent her last birthday when the couple was together without her better half. It’s true, Jessica had proclaimed on Twitter that she was excited for her upcoming birthday bash, and then, on the night in question, it turned out that she spent it alone with her mom and sister … and Romo was seen by paparazzi at a local restaurant with his friends. According to a source, his friends had taken him out for some fun before the start of training camp.

Definitely not the spitting image of a united front; for her to spend her birthday without her partner was indeed telling and fans everywhere were pretty much made aware that there was definitely trouble in paradise. It was only found out later that he had broken up with her the night before. It wasn’t long before it was made official and that’s when fan after fan asked the glaring question: Why?

9 Was Nick Lachey A Factor?

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Jessica Simpson was no stranger to being with A-list celebrity men, as you’ll soon find out as you read on, but probably the most famous or infamous was her first celebrity love, and he came in the form of a former boy band front man, Nick Lachey.

The two were together from 2002 until 2006 and their relationship was definitely public … especially since they were the stars of their very own reality show, Newlyweds: Nick and Jessica on MTV. It was on that show that Simpson entered the homes of millions and was accepted into their hearts. The chemistry the two had has made many speculate whether their relationship was a leading factor to the destruction of Jessica and Romo’s relationship. Could it be that the star football player was actually threatened by a member of 98 Degrees?

8 Her Sister Ashlee Had Her Back Through It All

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Always close, sisters Jessica and Ashlee are inseparable. They spend a lot of her time together and often go to each other in times of turmoil and need. When Ashlee had her lip singing fiasco on Saturday Night Live in 2004, when it was revealed to the world that she was lip singing to a recorded track, it was her sister Jessica that supported her and comforted her through that tumultuous and embarrassing time.

And so when Jessica came under fire for having apparently gained too much weight, it was Ashlee that came to her defense publicly. And so it was no doubt that when she and Romo were over, she came to her sister’s defense once more, giving her sister support both publicly and at home.

7 Their Last Public Appearance Was With A Controversial Figure

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As it has been reported, their last appearance in public together was made with none other than Tiger Woods himself; yet another public figure who isn’t a stranger to tabloid news. He saturated news feeds for months when it was found out that he had had numerous affairs with many, many women while being married. On July 1st, 2009, the couple attended The National Golf Tournament in Bethesda where she sang the national anthem and Tony played a round of golf with Woods.

This would mark the final days for the couple, as he would officially break up with her on the 9th of July. Was it a case of bad company in being around Tiger? Hardly … it just turns out that their last days were spent with a dude that had his own set of problems. Maybe misery does love company.

6 She Was Jealous Of John Mayer And Jennifer Aniston

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Jessica dated John Mayer from 2006 to 2007 and the two made headlines as both are pretty famous for their antics behind closed doors. It has been noted that the two had a very physical relationship—even Mayer has gone on record stating as much, gentleman that he is.

Well, the point is, many close to Jessica stated that when she found out that Mayer had started to see former Friends star, Jennifer Aniston, she actually got jealous and it affected her deeply. She was with Romo at the time, and this source says that she wasn’t over what they had. Simpson has never justified or denied these claims as she probably never will, but the seed was planted in the minds of people everywhere.

5 She Was Blamed For His Bad Performance On The Gridiron


There was a time when she was called “Yoko Romo,” a reference to Yoko Ono, the factor that Beatle maniacs believed was the cause to the breakup of The Beatles after her relationship with John Lennon began.

RELATED: Things About Tony Romo The NFL Wants Forgotten

Dallas Cowboys fans definitely showed their distaste for the couple’s union and they let their voices be heard. Boos were consistently heard in the stands when Simpson was present at games. They ultimately felt that she was the reason he was playing badly. It’s also reputed that ex-president George W. Bush also put his precious two cents in when he agreed with the majority of Cowboy fans and stated that she was indeed the cause for Romo’s bad performances on the field. But can his playing really be blamed on his then significant other?

4 Her Moment With Kenny Chesney

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There was also a time when the internet and the tabloid press were abuzz with the very disturbing rumour that Jessica had a not so secret fling with Romo’s buddy, country singer Kenny Chesney. Sources who attended a party held at their home said that Jessica and Chesney had gotten quite flirtatious as the festivities began to roll on. Chesney denies all claims, but people close to the star have definitely laid claim to the fact that Jessica is very flirtatious and they can understand how it must have seemed to witnesses.

Romo was obviously present and sources say that he hadn’t been the same since seeing her with Chesney at the party. Of course there are many conflicting theories as to what really happened, and of course Chesney would never admit to flirting with a best bud’s girl, so speculation is all we’ll get for now.

3 She Was Too Wild For Him

via people.com

It’s no wonder that Hollywood celebs like to party hard. Most of them burn the candle at both ends, working and playing much too hard, as was the case for Jessica. Yes, she worked hard at her singing, but when the time came to have a good time, she wasn’t one to shy away from some fun and everything that came along with having a good old time. Sources close to her say she’s one to drink and eat quite a bit at parties, enjoying herself to the fullest.

Yet that’s not always the case for athletes. Sure, some athletes are pretty famous for living the night life to its fullest, yet apparently, that wasn’t the case for Romo. Many have speculated that Jessica’s hard partying ways were too much for the football star.

2 He Had Enough Of Her History With Other Men

via allure.com

It’s no secret that Jessica has indeed had a tumultuous and “busy” history with men. It’s inevitable when it comes to a celebrity as utterly gorgeous and flirtatious as she undeniably is. It just goes with the territory. John Mayer actually went on record as saying that Jessica Simpson was addictive and he was head over heels into her.

It must have been extremely difficult for Tony Romo to constantly have to hear such stories in the press and still try to create some sort of stability with Jessica. Many close friends to the ex-football star have claimed that he wasn’t impressed with her magic number of how many exes she actually had, which was apparently quite high. Not many men would be at ease with that.

1 She Had A Lot of Growing Up To Do

via etonline.com

As is the case with many celebs that have attained their dreams at a young age, the harsh realities most people face aren’t a factor in their everyday lives. Such an existence breeds a certain type of childish character in the individual leading them to remain in a perpetual state of adolescence and therefore can lead to them having problems facing an inevitable future.

In Jessica’s case, she was starting to face that reality when she was with Romo. Her career was winding down and that was hard for her to face. Many have speculated that maybe Romo, who always had a pretty good head on his shoulders, had no patience to wait for her to grow up and face her future. This could be, but she has indeed come a long way and finally seems happy. Looks like she found her way there eventually.

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