It was the late 2000s and you couldn't check out at a grocery store without seeing their faces on a tabloid. Jessica Simpson. Tony Romo. It was the ultimate "it" couple—the blonde pop princess and the star quarterback of America’s Team. But looking back now, it wasn't just a romance; it was a cultural flashpoint that basically invented the modern "WAG" scapegoating we still see today.
Honestly, the way people treated Jessica Simpson back then was wild.
If Tony Romo threw an interception, it was her fault. If the Dallas Cowboys lost a playoff game, she was the "jinx." Fans literally showed up to Texas Stadium with masks of her face to mock her. It was a lot for a relationship that started because Romo told reporters she was his celebrity crush.
How it actually started
They met in November 2007. Simpson was watching an NFL game with her family when the announcers mentioned Romo had a crush on her. Her dad, Joe Simpson, ended up being the bridge. He got in touch with Romo, and the two met up shortly after.
It was fast. By Thanksgiving, they were together.
For a while, it seemed perfect. In her 2020 memoir Open Book, Simpson described him as a "solid person" who felt like the kind of guy she always imagined marrying. But the honeymoon phase didn't last long once the "jinx" narrative took hold. In December 2007, she wore a pink Romo jersey to a game against the Philadelphia Eagles. The Cowboys lost. Romo played poorly. Suddenly, the internet (which was a lot meaner back then) decided she was the reason for his stats dropping.
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The Cabo trip that broke the internet
The peak of the drama happened in January 2008. Before a massive playoff game against the New York Giants, Romo took Simpson on a quick vacation to Mexico.
The photos of them lounging by a pool became the stuff of legend. When the Cowboys lost that playoff game a few days later, the city of Dallas basically revolted. Even teammate Terrell Owens famously said she wasn't a "fan favorite" in the locker room.
Simpson later admitted in her book that the public hate was devastating. She expected Tony to stand up for her. She wanted him to tell the fans to back off. He never really did. That silence created a rift that most people didn't see from the outside.
The John Mayer of it all
Why did they actually break up? It wasn't the football fans. It was an email.
By July 2009, things were already tense. Simpson had an "on-again, off-again" history with John Mayer that just wouldn't quit. She has been very open about the fact that Mayer had a "hold" on her. Even while she was with Romo, Mayer was reportedly still trying to get back with her, even allegedly asking her parents for her hand in marriage while she was dating the QB.
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The end came the night before Jessica's 29th birthday.
Romo found an email from Mayer to Simpson. Even though she insisted she hadn't cheated, the trust was gone. Romo broke up with her right then and there. Two years of dating ended over an email.
The $100,000 boat and the plastic cups
Here is a detail that just resurfaced recently in 2025. Back in 2009, for Romo’s 28th birthday, Jessica bought him a luxury speedboat worth $100,000.
Flash forward to late 2025. Simpson revealed during a benefit concert that Romo actually called her mom, Tina, recently. Why? He was finally selling the boat after all these years. But since Jessica's name was still on the title, he needed her to sign the paperwork.
His "thank you" for her help? A set of plastic cups.
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Simpson’s reaction was classic: "I'm like, 'Wow, I'm glad we didn't work out.'"
What we can learn from the Jessica Simpson and Tony Romo era
Looking back, this relationship was a masterclass in how the media treats women in sports. Simpson was a successful businesswoman and singer, yet she was reduced to a "distraction."
If you're following a high-profile celebrity relationship today, remember these takeaways:
- Performance is rarely about the partner: Athletes have bad games. Attributing a professional's failure to their girlfriend is usually just lazy analysis (and often a bit sexist).
- Trust is the baseline: No matter how famous you are, a relationship can't survive if "exes" are still hovering in the inbox.
- The "Jinx" is a myth: Romo went on to have a great career and is now one of the highest-paid broadcasters in history. Simpson built a billion-dollar fashion empire. They both did just fine once the cameras stopped chasing them as a pair.
The saga of Jessica Simpson and Tony Romo serves as a reminder that what we see on the sidelines is only about 10% of the actual story. Relationships are messy, especially when you throw in a $100k boat, a meddling ex, and 80,000 screaming football fans.