Think back to 2006. Low-rise jeans were everywhere. Reality TV was just starting to get its teeth into us. And then, there was the pairing that literally nobody saw coming but everyone couldn't stop looking at: Jessica Simpson and John Mayer. It felt like a glitch in the Hollywood matrix. You had the quintessential "American Sweetheart" pop star, fresh off a very public divorce from Nick Lachey, suddenly linked to the moody, hyper-intellectual "Your Body Is a Wonderland" guitar god.
It wasn't just a fling. It was a three-year cycle of high-intensity passion and brutal emotional exhaustion.
Honestly, looking back at it now through the lens of Jessica’s 2020 memoir, Open Book, it sounds less like a romance and more like a psychological thriller. She didn't hold back. She described a relationship that was "on and off" so many times—nine times, to be exact—that it’s a wonder either of them knew if they were actually single or taken on any given Tuesday.
The Obsession Phase
They met at a Clive Davis Grammy party in 2005. Jessica was still technically married, but the spark was there. Mayer told her he loved her song "With You." Subtle? No. Effective? Absolutely. Once her divorce was finalized in 2006, they went full throttle.
Mayer didn't just date her; he was obsessed. That's the word she used. Obsessed. He told her he wanted "all of her or nothing." It sounds romantic in a song lyric, sure, but in real life? It's a lot of pressure. Jessica mentioned that he would walk into a room, pick up a guitar, and she would just melt.
But there was a darker side to that "intellectual" connection.
Jessica admitted she felt like she wasn't smart enough for him. Imagine that. You’re a global superstar with a billion-dollar fashion empire, and you’re sitting there obsessively proofreading a text message because you're afraid of a typo. She actually had friends check her grammar before hitting send to John. She felt like every conversation was a competition he had to win.
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"He was so clever and treated conversation like a friendly competition that he had to win." — Jessica Simpson, Open Book
To deal with the nerves of just talking to him, she started drinking. It’s a heavy detail she shared—that the anxiety of trying to keep up with his mind was what really kickstarted her reliance on alcohol at the time.
The Nine Breakups and Tony Romo
If you think your toxic ex was bad, consider the "nine times" rule. John would break up with her—often via email, which is just cold—and then come back claiming he finally realized he loved her.
It was a cycle.
He even managed to mess up her relationship with NFL star Tony Romo. While she was dating Tony, John was still in the wings, sending emails, staying close to her family, and basically being a ghost that wouldn't stop rattling chains. He even told her family at one point that he loved her and they could trust him. Spoiler: they probably shouldn't have.
Tony Romo eventually saw a message from John on her phone and that was that. The "hold" John had over her was something she compared to an addiction.
The "Sexual Napalm" Moment
Everything changed in 2010. By then, they were mostly over, but the final bridge didn't just burn; it exploded. John gave a now-infamous interview to Playboy.
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In the middle of a rambling, controversial conversation, he called Jessica "sexual napalm." He thought he was giving her a compliment. He thought he was being "raw" and "edgy." Instead, he humiliated her. Jessica was floored. She was embarrassed that her grandmother would read those words. It was the moment the "loyal" version of John she had built up in her head died.
She deleted his number.
She realized he had been using their drama as "material" for his songs. He was breaking her heart to get a better bridge for a ballad. That’s a tough pill to swallow when you thought it was true love.
What we can learn from the "Mayer-Simpson" era
It’s easy to dismiss celebrity drama as fluff. But the Jessica Simpson and John Mayer saga is a textbook look at "anxious-avoidant" attachment styles before those terms were all over TikTok.
- Intellectual posturing is a red flag. If someone makes you feel like you need a dictionary and a proofreader just to send a "Hey" text, they aren't "smart"—they're making you feel small.
- The "On-Again, Off-Again" trap. If it takes nine times to figure out it doesn't work, it doesn't work. The passion of the "reconciliation" is usually just relief that the pain stopped for a second.
- Public respect matters. How a partner speaks about you to others—or to millions of readers—is the ultimate test of their character.
If you find yourself in a cycle where you're drinking to mask nerves or editing your personality to fit someone else's "intellectual" standards, take a page from Jessica's 2026 perspective. She eventually found peace with Eric Johnson, a relationship she describes as easy and respectful.
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The best thing you can do if you're stuck in a "napalm" relationship? Delete the number. Don't wait for the tenth breakup.
Check your own relationship for "conversational competition." If you feel like you're losing a game every time you talk, it might be time to stop playing.