He got down on one knee just four months later and popped the question aboard a yacht in Hawaii just before Valentine’s Day. They held their wedding in Austin, Texas on October 26, 2002.
The 90s and 00s were a weird time where it was still OK to ask pop stars about their virginity. While Jessica's contemporaries Britney Spears and Christina Aguilera would try and dodge such questions, Jessica turned being a staunch Christian church-goer (her father was a preacher) into her gimmick and openly spoke about wanting to wait until she was married to have sex.
She lost her virginity to Nick on her wedding night later telling Blender magazine: "It was the most amazing moment of my life. I’m so lucky I didn’t lose my virginity in the back of a Jeep or something. Instead, I had this amazing, elaborate wedding and I topped it off with that.”
She also released the song, Sweetest Sin, in 2003 about losing her virginity to Nick but it failed to reach any commercial success, so it was around this time that Jessica's father and her manager, Joe Simpson, pitched an idea to MTV about a reality show starring the couple, which resulted in Newlyweds: Nick and Jessica.
The series was initially meant to focus on the marriage between Michael Jackson and Lisa Marie Presley but they backed out.
It premiered on August 19, 2003, instantly became a pop culture phenomenon, with Simpson's "dumb blonde" antics helping to make the couple a household name.
Her most famous quote to date is when she asked Nick: "Is this chicken, what I have, or is this fish? I know it's tuna, but it says 'Chicken... by the Sea'." She was sitting on the sofa eating a can of tuna by the brand Chicken of the Sea.
Nick's patience mixed with Jessica's naivety was a ratings success for MTV and it would air 41 episodes throughout three seasons until 2005.
They pair also starred in the ABC special The Nick and Jessica Variety Hour in April, 2004, which featured guest appearances by celebrities such as Jewel and Mr. T, among others.
But cracks were also starting to show, in particular, when fights would break out over Jessica's inability to clean up after herself. Or the time Nick got mad at her for spending $750 on La Perla lingerie, or $1,200 on sheets.
They also couldn't agree on how many times a week they should have sex. Nick suggested three times, but Jessica didn't sound so keen.
“You could feel there was tension between the two of them. They were very different people. He was a blue-collar guy, he did a lot of things himself, like he and his brother would build things. He was frugal, and she had excessive taste. In the end, they weren’t suited for each other. The only thing they really had in common was their music,” Newlyweds producer Sue Kolinsky told Complex in 2017.
“She was really young; I think he’s seven years older than her. He wanted a family, and her father thought maybe she was too young. Her father was very involved in her life,” Kolinsky continued.
The show concluded on March 30, 2005, and the pair filed for divorce that December with Jessica citing irreconcilable differences. On June 30, 2006, Jessica and Nick's divorce was finalised.
Their break-up was one of the biggest tabloid stories of the 2000s, with their marriage split splashed across magazine covers for months on end.
Nick said he was "blind-sided" by the divorce, while Jessica described it as gut-wrenching.
"I loved everything about marriage. I loved having a companion to wake up with and have barbecues with. But things happen and people grow apart. I don't really ever talk about the divorce because it was a heart-wrenching thing to go through. It's a very, very personal thing," she said.
She was so devastated, she thought that she would never marry again.
“It was hard to imagine I would ever walk down the aisle again,” she told Glamour in 2009.
“It was like a death in the family. You go through the mourning stage, then the rebellion, and then all of a sudden you have to find life by yourself. Once you do that, you feel complete and that’s the only time you can truly fall in love again, and give yourself over completely to another person.”
In 2014, she married NFL star Eric Johnson, with whom she shares three children, Maxwell, Ace, and Birdie.
Nick also went on to marry Vanessa Minnillo after they met in 2006 when she appeared in the music video for his tear-jerker title track of his album What's Left of Me, which became the biggest single of his solo career to date.
They married on July 15, 2011 at Sir Richard Branson's private Necker Island in the British Virgin Islands and have three children together Camden John, Phoenix Robert and Brooklyn Elisabeth.
As well as having a booming, billion-dollar fashion brand, Jessica recently revealed that she would be coming out with a memoir and it will be released in February 2020.
According to the publisher, the book will cover all aspects of Simpson’s life, “from her popular television show Newlyweds, to a very public divorce, starring on the big screen and topping the Billboard charts, finding new love, raising a family, and running a successful business empire.” The tome “will be a candid, inspiring, and behind-the-scenes look at how she chose to learn from each difficult moment, evolve musically, become a more fearless businesswoman, and consistently shatter all expectations of who she was ‘supposed’ to be.”