Jessica Simpson is finally back on the market, and honestly, it feels like the end of an era. After over a decade with former NFL player Eric Johnson, the news of their 2025 separation sent shockwaves through anyone who followed the early 2000s tabloids. We’ve seen her go from a "teenage virgin" icon to a reality TV pioneer, a scorned ex-wife, a "sexual napalm" muse, and eventually a billion-dollar business mogul. But if you look closely at the Jessica Simpson dating history, it’s not just a list of famous men. It’s actually a pretty wild roadmap of a woman trying to find her own voice while some of the most famous men in the world were trying to drown it out.
Right now, she's 45, looking better than ever, and making it very clear she isn't interested in being The Bachelorette. She told reporters at LAX recently that she’s got "options." And honestly? Good for her.
The Nick Lachey Years: Reality TV’s First Casualty
Before the world knew what a Kardashian was, we had Nick and Jessica. They met at a Hollywood Christmas Parade in 1998. She was 18. He was 24 and the lead singer of 98 Degrees. It was basically a pop star fever dream. They broke up briefly in 2001 because she wanted to focus on her career—which her dad, Joe Simpson, was famously protective of—but 9/11 changed everything. Jessica has said that the tragedy made her realize she never wanted to be without him.
They married in 2002. Then came Newlyweds.
Most people remember the "Chicken of the Sea" moment, but the reality was much darker. In her memoir Open Book, Jessica admitted that by the third season, they were barely speaking. She felt like a "trophy" he didn't really want to display. The lack of a prenup ended up costing her about $12 million when they finalized their divorce in 2006. She’s since called that her "biggest money mistake," which is a pretty relatable way to describe a multimillion-dollar divorce settlement.
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The Johnny Knoxville "Emotional Affair"
While she was still married to Nick, Jessica filmed The Dukes of Hazzard. This is where the Johnny Knoxville rumors started. For years, they both denied it. But in 2020, she finally came clean: it was an "emotional affair."
She described it as being "prison pen pals," exchanging flowery letters while they were both married to other people. She felt a connection with Johnny that she wasn't getting at home. He made her feel smart and adventurous. Even though they never actually slept together, she felt the betrayal was almost worse because of the deep emotional bond. It’s a nuance that a lot of people miss when they just look at the headlines from that era.
John Mayer and the "Sexual Napalm" Era
If Nick was her first love, John Mayer was her first addiction. They started an on-again, off-again cycle in 2006 that lasted for years.
Honestly, it sounded exhausting.
Jessica wrote about how she felt she had to "win" conversations with him. She was so insecure about her intelligence around him that she would have friends check her text messages for grammar mistakes before hitting send. Think about that for a second. One of the most famous women in the world was terrified of a typo because she didn't want her boyfriend to think she was "dumb."
Then came the 2010 Playboy interview.
Mayer famously called her "sexual napalm" and compared her to "crack cocaine." While he probably thought he was complimenting her, Jessica was humiliated. She was worried about her grandmother reading it. That was the final nail in the coffin. She deleted his number and never looked back. It’s a classic example of how a "passionate" relationship can actually just be toxic.
Tony Romo and the "Yoko Romo" Drama
In between the Mayer breakups, there was Tony Romo. They started dating in 2007, and it seemed like a match made in Texas heaven. Until it wasn't.
Cowboys fans were brutal. They blamed her for his poor performances on the field, calling her "Yoko Romo." But the real reason they split in 2009 had nothing to do with football. It was John Mayer. Again.
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Tony found out that Jessica had stayed in touch with John. Specifically, he found an email. Even though she hadn't cheated physically, the trust was gone. He broke up with her the night before her 29th birthday. Imagine being Jessica Simpson, about to turn 30, and getting dumped by a superstar QB because your toxic ex won't stop emailing you. Rough.
The Decade of Eric Johnson
For a long time, it looked like Eric Johnson was the "one." They met in 2010 when a mutual friend invited him to her house. He was a former NFL tight end, recently separated, and reportedly "met her on all levels."
They didn't rush the wedding—mostly because they kept having kids. They had Maxwell in 2012 and Ace in 2013 before finally getting married in 2014. A third child, Birdie Mae, followed in 2019. For ten years, they were the picture of stability. Eric even stopped drinking when Jessica decided to get sober in 2017.
But by late 2024, rumors started swirling. He was spotted without his ring. They were living separate lives. In January 2025, she officially confirmed the separation. It wasn't a "scandal" like her previous breakups; it just felt like two people who had grown apart after 14 years together.
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The Mystery "Movie Star" and What’s Next
One of the funniest bits of the Jessica Simpson dating history is the "Movie Star" she wrote about in her Amazon essay. She never named him, but she described a secret romance with a "massive" actor she grew up idolizing. Fans have guessed everyone from Mark Wahlberg to Jensen Ackles (who she actually did date briefly when she was 18). Whoever it was, it was a short-lived fling that reminded her she didn't want to be "the other woman."
So, where is she now?
As of early 2026, Jessica is leaning into her "single mom" era. She’s mentioned she’s into "younger men" lately because they appreciate the confidence of an older woman. She’s not on the apps yet, but she’s definitely out there.
Lessons from Jessica’s Love Life
If there’s anything to take away from her journey, it’s these three things:
- Don't ignore the "emotional" red flags. The Johnny Knoxville situation showed that sometimes the strongest connections happen when you’re looking for what’s missing in your current life.
- Your partner should make you feel smart. If you're proofreading texts to avoid being judged, you're in the wrong room.
- Independence is the best revenge. She’s worth hundreds of millions of dollars now. She doesn't need a man to pay the bills or define her status, which is probably why she seems so chill about being single at 45.
If you’re looking to channel some of that "newly single" energy, maybe start by doing a digital declutter. Delete the numbers of the people who make you feel like "sexual napalm" but don't actually respect you. It worked for Jessica.
Next Step: Take a page out of Jessica’s book—literally. If you haven't read Open Book, it's the best way to see how she processed these relationships in her own words. It's way more insightful than any tabloid headline from 2005.