John Mayer’s Biggest Betrayal in Jessica Simpson Relationship Was His Perez Hilton Kiss

These days, Jessica Simpson is happily married to Eric Johnson, and the two of them are parents to three beautiful children. However, it wasn’t too long ago that the singer turned fashion designer was newly divorced from Nick Lachey and in search of the perfect romantic partner.

It was in 2006 that she began a relationship with John Mayer, and it was anything but easygoing. In fact, some fans were left a little confused by the whole thing, and according to a source, the relationship took its toll on her.

It can’t be easy to date someone while the entire world is watching, especially when there are plenty of other celebrities just waiting to voice their opinions. Still, that is exactly what Simpson, who now keeps most details about her personal life under wraps, had to deal with when she was dating Mayer.

A lot of things famously happened between the couple, and we now know that Mayer’s biggest betrayal to Simpson was his Perez Hilton kiss.

John Mayer and Jessica Simpson had an on-and-off relationship

John Mayer and Jessica Simpson
John Mayer and Jessica Simpson | Kevin Mazur/WireImage

Simpson and Mayer were both fresh out of other relationships when they met, yet they decided to move forward and give things a go. The two of them had an on-and-off relationship for about two years, and in an interview, Mayer even said that “she’d had a huge effect on him.”

From all outward appearances, they seemed to be pretty happy together, being photographed quite often, and always looking at each other with affection. Even so, the relationship was not what it seemed, nor was it destined to last, and in 2007, the on-again-off-again couple called it quits once and for all. 

The relationship definitely had its ups and downs

Jessica Simpson smiling
Jessica Simpson | Michael Stewart/Getty Images

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Just about every relationship has its good times and bad, but for Simpson and Mayer, it was pretty extreme. Simpson recently opened up in a new memoir, saying that her ex-boyfriend was “obsessed with her.”

So, what happened exactly? Simpson caught the attention of Mayer in 2005 when she released one of her biggest hits “With You.” He liked the song so much that he began writing her letters, and soon after the end of her marriage to Lachey, they began dating.

Even a few years after their breakup, Mayer continued to humiliate Simpson, famously saying during an interview that she was like “sexual napalm.” Although he may have thought that Simpson would view this as a compliment, it was quite the opposite, and she responded by saying: “I was floored and embarrassed that my grandmother was actually gonna read that.”

John Mayer’s biggest betrayal involved Perez Hilton

While it might seem that Mayer’s “sexual napalm” comment was the worst thing that he possibly could have done, it turns out that it wasn’t his biggest betrayal.

So, what was? According to a source, it was the singer’s kiss with Perez Hilton in 2007 that shocked and upset Simpson more than anything. At the time, Hilton, a celebrity blogger who is known for being blunt, was giving Simpson quite a hard time. He was doing things such as calling her “Jessica Simpleton,” and even insulting her younger sister, Ashlee.

Arguably, this is why Mayer’s biggest betrayal is his kiss with Hilton — Mayer chose to lock lips with someone who repeatedly brought her down. To make matters worse, Mayer was the one who initiated the smooch.

“Her friends were horrified” the insider told Page Six, “but she didn’t care. John couldn’t do anything wrong, as far as she was concerned. She was absolutely head-over-heels in love with him.”

In “TMI: My Life in Scandal,” Hilton said Simpson appeared mortified and covered her face with her hair. He claimed Mayer looked “satisfied” post-kiss and Simpson “didn’t seem to know whether she was incredibly embarrassed or really turned on.”