When you’re young and beautiful in Hollywood, it seems that everyone wants to be you, be like you, date you, and so on. It must be nice to be the picture-perfect girl that everyone hopes to get someday, like Jessica Simpson. I mean, take one look at her – it’s obvious, isn’t it?
Jessica Simpson is a Texas native with the voice, and the looks, of an angel. She’s had a lengthy career and a laundry list of lovers who have spent their most intimate moments with her. From musicians to actors to athletes and pranksters – this is Jessica Simpson’s love life and all the shenanigans she has gotten up to in between lovers!
Who Is Jessica Simpson?
Jessica Simpson is a singer and actress hailing from the Lone Star State. This Abilene, Texas native has stolen our hearts for ages but did not really take off in her career until her later teen years. She grew up in Dallas and Waco, Texas but also spent time with her family living in Cincinnati, Ohio.
The daughter of a minister, Simpson was raised in a religious home. Her father gave her a purity ring when she was just 12 years old, signifying her promise to God that she would abstain from sex until she was married. Her virginity was often focused on during her rise to fame.
Her mother was a homemaker, and her father was a Baptist minister. They were involved with their church community, where Jessica sang in their choir. It was actually a Christian music label that first gave her a chance after her auditions for the Mickey Mouse Club did not work out in her favor.
She was first signed by Proclaim Records, a Christian music label, which immediately wanted to represent her when they heard her sing “I Will Always Love You” by Dolly Parton. Proclaim was supposed to release her debut album. Her dad made her quit for reasons that might upset you.
Body-Shamed by Dad
Her father claimed that she had to quit the Christian tour she was on because she started to fill out her bra, a little “too much,” as if her body’s natural development would get in the way of her ability to perform. No, that wasn’t the case he made, though he did talk about how her developing body changed everything.
He said that she needed to stop touring because the growing size of her breasts sexualized her performances instead of leaving them wholesome. I don’t know if Jessica had any say in this, but it might be safe to say that put an uncomfortable focus on her that growing girls don’t typically enjoy.
She began singing in the church choir when she was eleven years old, and she realized her dream of becoming a singer when she was at a church retreat. Not long after, she started her path to stardom when she auditioned for the Mickey Mouse Club, much like many of today’s biggest stars.
Her auditions for the Mickey Mouse Club were going well until the very last moment. She auditioned with a rousing rendition of “Amazing Grace,” and she showed off her dance moves to “Ice, Ice Baby.” She advanced to the semifinals along with artists we know today, like Britney Spears, Christina Aguilera, and Justin Timberlake.
Close but Not Quite
Jessica Simpson once said that she knew she wasn’t going to be selected for the Mickey Mouse Club as soon as she auditioned. She did advance as a semifinalist, but years later, she admitted to being shaken by Christina Aguilera’s performance, saying that it threw her off and made her nervous to follow.
In her memoir, Simpson wrote that she “just froze” when her time came. “My choreography was completely off, and then I couldn’t remember any of the lines from my monologue. I stared at the camera and knew I’d blown it completely. The theater was silent.”
Timberlake Made It Worse
After freezing in front of the crowd like that, Simpson ran off stage and tried her best not to burst out into tears. She ran into Justin Timberlake, who was just about to go perform himself. He dug into her insecurities and opened his eyes wide, saying, “Oooooooooh, what did you just do?”
In her memoir, she wrote, “That started the tears. Oh, I cried. I cried big heaving sobs. My parents came to me, asking again and again, ‘What happened? What Happened?’ I choked. I crashed down to earth, landing right on top of them.” It seems she managed to move on from this incident!
Catching Tommy’s Attention
The rise of her career had many contributing factors. When the Christian music label went bankrupt, her grandmother personally funded her debut album. The album, Jessica, was sent to several record labels and ultimately caught the attention of Tommy Mottola, who was married to Mariah Carey at the time.
Mottola was more than just Mariah Carey’s husband – he was also the head of Columbia Records! He felt that she was different than Britney and Xtina, saying that Simpson could “really sing.” The other two artists had so much sex appeal in their marketing; Mottola wanted Simpson to be the opposite of that.
Her Rise to Fame
You could say that the rest is history, as Jessica Simpson worked her way up the Billboard Top 100 and into the public eye like a star. As she rose to fame, she would end up having fantastic opportunities only offered to the best of the best. Some of these experiences include her halftime show at the Super Bowl XXXVIII.
Her rise to fame also influenced the relationships she would find herself in later. She was loaded up with once-in-a-lifetime opportunities that anyone would be grateful to have, including a duet she performed at the 2001 Presidential Inauguration of George W. Bush. That is a tremendous honor for anyone!
Her Tumultuous Love Life
No surprises here to learn that Jessica Simpson has had a wide range of boyfriends. She’s a beautiful girl with the voice of an angel, and she certainly had her pick of men whose hearts she would later end up breaking. She’s even tried marriage a couple of times.
If you take away one thing from her dating history, it’s that she definitely has a type. She has dealt with her relationship ups and downs like any other person, struggling with infidelity and being faithful to her partners. These relationships don’t define her but rather contribute to the direction she took in life.
She Dated Jensen Ackles
Back during her rise to stardom, Jessica Simpson dated Jensen Ackles. She dated the Supernatural actor in the late 1990s, around the same time that she started making headlines. They dated when her first album, Sweet Kisses, was released. Some even speculated that she never got over him.
Simpson reflected on this relationship when she talked about her “first heartbreak” on Newlyweds: Nick and Jessica many years after. It seemed these two Texas kids fell hard for each other, even though it didn’t work out in their favor. Life goes on, and both of them have since moved on!
The Nick Lachey Files
Nick Lachey and Jessica Simpson met at a Christmas party in 1999, and they were instantly hooked. He knew about her abstinence pledge to wait to have sex until she was married, and it was speculated that she did not actually save her virginity for their wedding night – but who knows?
The night that they met, Lachey admitted to calling his family and swearing he would marry her one day. They began dating in 1999 and were married in October 2002. Together, they starred in MTV’s Newlyweds: Nick and Jessica for three seasons. Even when their relationship ended in divorce, she mostly had great things to say about him.
Nick’s First Memories of Jessica
Back in the day, Nick Lachey told People magazine that he instantly knew that she was the girl for him. “The first time I ever heard her sing, I got chills, and I told the guys, ‘I’m going to marry that girl one day.'” He kept his word and waited for the abstinent pop star until they were finally wed.
Their relationship had many ups and downs (as any relationship does, no matter how famous you are), but something significant that came up was Lachey’s jealousy of his wife’s rise to fame. When their relationship began, he was the more famous of the two, but by the end, the tables had turned, and she was in the spotlight more often.
Her Rise to Fame Ruined Their Relationship
At the time they began dating, 98 Degrees was constantly topping the charts. Nick Lachey was comfortable and happy with his relationship dynamic with Jessica Simpson because it served what he was looking for. When she started ranking higher than he did, that was when his career began to fizzle out, as well as their relationship.
He told Rolling Stone, “It breaks my heart that I couldn’t make Jessica happy. I wanted to be everything to my wife. I wanted her to look at me with love in her eyes, the way she did at the beginning, and have her feel like I was the most wonderful, awe-inspiring man on the planet. And when that stopped, it was the worst feeling in the world.”
He Wanted to Feel “Needed”
Sure, this is a staple of successful relationships. Some partners are co-dependent, while others are fiercely independent, lone wolves. Simpson reflected on Lachey’s need for her to be dependent on him; he was “proud” of her successes but did not like it when she was able to stand on her own without him.
In her memoir, Simpson wrote, “he also wanted somebody who could make him feel like I did when I was nineteen years old, fawning all over him. I don’t think he understood how to have the kind of relationship where I didn’t need him to tell me what to do. It was not a happy time for us.”
He Was Her First Love
The two were smitten with each other from the beginning. Their relationship began when she was 18, and he was 25; she wrote in her memoir that he was her first love. They were engaged in Hawaii in February 2002 and were married in a big Texas wedding that October.
“Nick loved the fact I was so strong in my faith and that I had this wide-eyed, innocent approach to life. When he proposed in 2002, I said yes.” Not long after they said their vows, they became the centerpiece of MTV’s reality show, Newlyweds: Nick and Jessica. This show displayed their marriage for the world to see.
Imagine feeling the need to put on a show, pretending your marriage is perfect on national television. This show exposed their problems, and Lachey even admitted on the show that he and Jessica didn’t know each other as well as they thought they did prior to getting married and moving in together.
A show producer for Newlyweds, Sue Kolinsky, later shared what she witnessed while filming Season Three with Complex. “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.”
Sue Kolinsky said even more. “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.” Yeah… that sounds like a good reason for a relationship to end. If you have different priorities, it’s probably time to call it quits.
Jessica Simpson filed for divorce from her Nick Lachey in December 2005, citing “irreconcilable differences,” which could be literally anything, but again, if a relationship doesn’t work, don’t push it. Some things just have an expiration date, and their marriage was one of them.
More Reasons to End It
Putting a new relationship on television for the world to see what’s happening behind closed doors certainly has the potential to put a strain on the relationship. Simpson said that the show put a lot of pressure on their relationship, which ultimately caused them to break up in the long run.
“We were young and pioneering our way through reality television, always miced and always on,” she wrote in her memoir. “We worked, and we were great at it, but when it came time to being alone, we weren’t great at it anymore.”
Honesty on Reality TV
Simpson continued to reflect on their time together. “We really got crushed by the media and by ourselves. I couldn’t lie to our fans, and I couldn’t give somebody hope that we were this perfect golden couple.” At least she was honest and open about what they dealt with; I’m sure her fans appreciated the honesty!
“I respect Nick very much, I was really young, and my success hadn’t really begun. He knew me as this young, innocent 18-year-old that had never been introduced to the world in so many ways. I went straight from my father to him. Nick’s very smart. He was eight years older than me, but he was also young.”
No Hard Feelings
“We meant a lot to each other, and we always will,” she continues. “I want to be very respectful because I married him for a reason, and we were together for seven years for a reason. He has a family now, and I would never say anything to disrespect that.”
Now, both Nick Lachey and Jessica Simpson have moved on. They are both married to other people and are both proud parents to some beautiful children. Lachey is now married to Vanessa Minnillo, and they have three happy children. Simpson married NFL star Eric Johnson, and they also have three adorable and happy children.
She Dated Adam Levine
I can’t tell if things ever got too serious between the two, but Jessica Simpson and Adam Levine shared some hot and steamy memories together. Back in 2004, she reportedly hooked up with the lead singer of Maroon 5. There was one problem, though – she was still married to Nick Lachey!
The January after they first reportedly spent some intimate time together, Simpson and Levine were spotted spending the night at Chateau Marmont, a landmark for Los Angeles celebrities.The following day, her pal CaCee Cobb picked her up – and she was still wearing his t-shirt!
Viva La Bam
Back in September 2006, Bam Margera of Jackass fame (the movies, that is… I don’t know if he is a jackass as a person or not!) told Howard Stern on his SiriusXM radio show that he and Jessica Simpson had gotten down and dirty at one point.
“We were just drinking margaritas and stuff, and you know, from there,” he said. “It was when her parents were away, and Nick was away,” he claimed. “It’s not a secret.” Bam Margera had his own silly show, Viva La Bam, which ran for five seasons on MTV. The show ran from October 2003 until August 2005.
An Emotional Affair
In 2006, Jessica Simpson was accused of cheating on Nick Lachey with hotshot Johnny Knoxville. The two co-starred in Dukes of Hazzard and continually denied allegations that they were romantically entangled while filming. Even though they denied it, she wrote in detail about their emotional ties.
When Simpson and Knoxville first got involved, they were both married to other people; Simpson to Lachey and Knoxville to his first wife, Melanie Lynn Clapp. In her memoir Open Book, Simpson reflected on the extent of their emotional affair and why she felt it was worse than a physical affair.
The Knoxville Files
“To me, an emotional affair was worse than a physical one. It’s funny, I know because I had placed such an emphasis on sex by not having it before marriage. After I actually had sex, I understood that the emotional part was what mattered. And Johnny and I had that.”
Simpson shared that these two lovebirds sent each other love letters. “It’s like Johnny and I were prison pen-pals, two people who wanted too much to be with each other but were kept apart — by bars, by our stars, by our respective spouses,” she wrote in her memoir.
The John Mayer Saga
By all accounts, these two had a tricky and overall unhealthy relationship. They started dating in 2006, and around that time, she famously darkened her beautiful, long blonde locks. Was this alluding to something more sinister in her relationship, a cause of concern? They broke up for the first time in 2007.
John Mayer may be a master lyricist, but he’s also a master creep from reports with other women throughout the years. During an interview with Playboy in 2010, Mayer opened up about his relationship with Simpson, claiming that being in bed with her was “like sexual napalm” and he compared their relations to dependency on harder drugs.
In her 2020 memoir, Open Book, she opened up about her relationship with Mayer and all of the road bumps that came along the way. “Again and again, he told me that he was obsessed with me, sexually and emotionally.” He also reportedly told her over and over again that he would dump her because her “light would start to dim.”
“John loved me when I was shining, and he drew inspiration from that light. When he tapped me dry, he looked at me like I was withholding something from him.” This seems to be a pattern that we see for people like John Mayer; if only that was the end of their story together.
Reflections of Him
“He’d dump me, then come back saying he had discovered he loved me after all. I always saw it as him mercilessly taking me in from the cold,” she wrote in her memoir. “Every time John returned, I thought it was a continuation of a love story while my friends saw a guy coming back for sex with some foolish girl.”
She wrote that it was emotionally draining to keep on being involved with him. After getting back together for the umpteenth time in London, “I felt the full intensity of his obsession with me. And it was a drug to me. He studied every inch of my body, every detail of my face. He photographed me constantly, to the point that I worried he was keeping souvenirs before dumping me again.”
An unfortunately all-too-common part of many toxic relationships is the breakdown of a partner’s self-esteem. This was certainly the case in Simpson’s relationship with John Mayer, as she was constantly feeling insecure about herself. She would reportedly spend hours and hours re-reading texts to send him.
She wanted to make sure that every part of her message was perfect – grammar, spelling, and so on – so he wouldn’t have anything to pick on her for. She dyed her hair darker and lived her life according to the restrictions Mayer placed on her. That’s simply not fair to her.
Cool the Obsession, Johnny!
While opening up about the relationship in her memoir, Open Book, she described a conversation that she had with her therapist. She recalled telling her therapist about how she was madly in love with him, and her therapist shocked her with what she least expected to hear: “That’s not love. You know that, right? I mean, he never loved you.”
That must have felt like such a gut punch. She could not believe what she heard; she asked her therapist what she meant. “He was obsessed with you; Love and obsession are so different. One is healthy. One is not.” That must have hit her like a ton of bricks.
She Felt Belittled by John Mayer
Something else this musical sensation reflected on in her memoir was that she didn’t feel like she was smart enough for Mayer. She wrote, “I constantly worried that I wasn’t smart enough for him. He was so clever and treated conversation like a friendly competition that he had to win.”
After a long, sloppy series of breakups, the two were finally done with each other – after a total of nine times breaking up and getting back together again. He tried reaching out to “apologize,” but she didn’t want it; “I didn’t accept his apology,” she said. “I deleted all his contact information from my phone. When he reached out to me, I changed my number and changed my email. Delete.”
She Dated NFL Star Tony Romo
Jessica Simpson and Tony Romo were in a relationship for roughly two years, but after claiming that things were “going good,” he ended up breaking up with her the night before her 29th birthday. You might not be able to tell this from the get-go, but things moved fast for the two, after he kissed her on their first date.
Not long after they started dating, they spent Thanksgiving together in Texas. The following month, Tony Romo played his worst game ever – all while his new girlfriend was in the stands. Some of his die-hard fans pinned the blame on Simpson, claiming that he was distracted by her, ultimately leading to their defeat for that game.
The Breakup Ensued
It’s pretty well known by many that these two had a rocky breakup. Tony Romo had heard some things about John Mayer interrupting a family event to express his love for Jessica, begging her to take him back. Fortunately, she managed to say no, but it still got back to Tony.
Romo was not having it and dumped her as soon as he found out about Mayer’s profession of love. Simpson hadn’t told him about the incident, and he was not happy about it. When Romo called it quits, Simpson went crawling back into the toxicity that was her relationship with John Mayer.
She Dated Billy Corgan
For a brief time in 2009, Jessica Simpson dated the Smashing Pumpkins frontman, Billy Corgan. Their relationship was not long – it seemed like he was maybe a much-needed palette cleanser from her hysterical relationships in the past. He reflected on his time with her in a relatively positive manner.
Corgan was relatively casual about their time spent together. “The stuff that I’ve seen doesn’t have any bearing to the reality that I’m in,” he told The Chicago Tribune in an interview in 2010. “It’s like being in a cartoon. It has nothing to do with what’s really going on or how I feel.”
She Dated Jeremy Renner
The TAG and Marvel Universe star Jeremy Renner dated Jessica Simpson for a brief time in the spring of 2010. Apparently, he stopped calling her abruptly. That’s right – Renner had the nerve to ghost Jessica Simpson, and for what?! Even if their relationship wasn’t serious, she definitely deserved better than that…
Simpson was naturally mad about being ignored, and a source later confirmed that things got nasty. Simpson reportedly showed up to Renner’s house one day, coming face to face with him and his new woman. From then on, Simpson saw him as a dirtbag!
She Kissed Justin Timberlake
Even though he taunted her as a child on the set of their Mickey Mouse Club auditions, the two shared some private moments later in life. Justin Timberlake reportedly kissed her on a bet he was in with his former Mickey Mouse Club star, Ryan Gosling.
“After [my] divorce and he was out of a relationship, he was, like, over at my house, and we shared a nostalgic kiss,” she stated. “Apparently, he and Ryan Gosling had a bet on who would kiss me first when they were 12 years old, so he texted Ryan and said he won the bet. And I was like, ‘Oh, OK, um, so we don’t kiss again? That’s done.'”
She Fell in Love With Eric Johnson
Eric Johnson is an NFL superstar, and now, Jessica Simpson’s husband. The two met by chance; “He knocked on my dreamy cottage door (sigh), I let him in and never let him leave.” She also shared that she fell “head over slippers in love” that very day.
The two only dated for six months before getting engaged in November 2010. The two did not end up getting married until 2014. Johnson was married before to Keri D’Angelo. Real love takes time, and you don’t always get it right on the first try!
They Were Open About Traumas
These two have managed to stay together through thick and thin. In her memoir, Open Book, she discussed how opening up to Johnson about the traumas she experienced in life helped their relationship grow stronger than ever. You need to have a partner who is supportive and understanding of what you’ve been through!
She shared that talking with him about being abused as a child and her struggle with alcoholism only made their relationship stronger. “In terms of my marriage to Eric, I have never felt more myself or more free; Eric and I have a true mind, body [and] soul connection.”
Johnson Sacrificed for Simpson
In July 2010, Us magazine confirmed that Eric Johnson pulled out of his prestigious two-year business MBA program at the University of Pennsylvania’s Wharton School of Business. He reportedly pulled out of the program to be closer to her, as he didn’t want to relocate and be far from her!
Granted, starting the program probably would not have done much more for his career – he was already pretty well established and connected. He might have missed out on an enriching education at the Wharton School, but he knows what he did and still stands behind it!
They Have Kids Together Now
First comes love, then comes marriage, then comes Jessica with a baby carriage! Simpson announced her first pregnancy by posting a photo on Twitter where she showed off her baby bump, dressed as a mummy. “It’s true, I’m going to be a mummy!” she tweeted to her loyal followers.
In March 2019, the couple welcomed their third child to the world. Their daughter, Birdie, was born on March 19th, 2019 and came in at a whopping 10 pounds and 13 ounces. They have two other children, Maxwell Drew and Ace Knute. They built a family they love and will cherish together, hopefully for the rest of their days on earth!