Jessica Simpson's Complete Star-Studded Relationship History

From rising to fame as a music superstar to transitioning into acting and even becoming a reality star, Jessica Simpson has been a prominent figure in Hollywood since the 1990s, often living her private life under the watchful eye of the public. Ever since she stepped onto the showbiz scene, Simpson has garnered attention with her long blonde locks and iconic Y2K fashion, but also with her star-studded romantic connections.

Simpson's love life is marked by high-profile relationships, and while her fans celebrated her various talents and applauded her career shifts, some of Simpson's past partners struggled to cope with her lifestyle. In a 2023 interview with People, she candidly touched on the topic, admitting, "I don't find it hard to love anybody, but I have always thought that I was hard to love, that I was too much for people, or [that] my schedule was too demanding."

Now a mother of three and married to former NFL player Eric Johnson since 2014, Simpson has moved past her previous romantic entanglements. Notably, she was once married to singer-turned-TV host Nick Lachey but Simpson has also been linked to musician John Mayer, NFL player Tony Romo, comedian Johnny Knoxville, fellow singer Adam Levine, and several other celebs. Suffice it to say, when it comes to love, she keeps it strictly A-list.

Jessica Simpson's first high-profile relationship was with Nick Lachey, who was best known as the lead singer of 98 Degrees. The two met in 1998 and quickly hit it off, collaborating on music and publicly gushing about one another. Notably, in 2001, they briefly hit pause on their romance. However, after the tragic events of 9/11, Simpson realized that she never wanted to be apart from Lachey, as she informed People, and the two reconciled.

The following year, Lachey proposed to Simpson, and the couple tied the knot just months later. Seizing an opportunity to share their married life with the public, they launched their reality TV show, "Newlyweds: Nick & Jessica," which ran on MTV from 2003 to 2005. The singer still remembers the experience fondly nowadays. "It was very real, and Nick and I actually had a lot of fun," Simpson clarified during a 2022 appearance on "The Real" talk show.

Despite their apparent marital happiness, Lachey and Simpson unexpectedly split in 2005, with media speculation suggesting that she'd had several affairs with her "Dukes of Hazzard" co-star Johnny Knoxville, musician Adam Levine, and possibly others. When speaking to GQ in 2005, the "Jackass" star claimed that he was just friends with Simpson. However, in a 2006 interview with Rolling Stone magazine, Lachey admitted that he never expected to get divorced from Simpson, confessing that he still wasn't sure whether she had cheated on him.

During her divorce from Nick Lachey, Jessica Simpson found herself facing allegations of infidelity involving Johnny Knoxville, with whom she had appeared in the 2005 comedy "The Dukes of Hazzard." Although Simpson didn't directly address the rumors at the time, she subsequently acknowledged in her 2020 memoir, "Open Book," having developed a deep emotional connection with Knoxville that made her reconsider her marriage to Lachey.

After Simpson realized she was attracted to Knoxville, who was also married at the time, she felt like "[she] couldn't trust [herself]." Although their relationship never became physical, Simpson and Knoxville exchanged love letters, with the singer describing them as "prison pen pals, two people who wanted so much to be with each other but were kept apart." 

In her memoir, Simpson also noted, "I could share my most authentic thoughts with [Knoxville]," adding, "He believed in me and made me feel I could do anything." Despite not cheating, Simpson admitted that, for her, "an emotional affair was worse than a physical one." She filed for divorce from Lachey in December 2005, citing irreconcilable differences.

Amidst the tumultuous Nick Lachey-Johnny Knoxville episode in 2005, Jessica Simpson also found herself being linked to Maroon 5 frontman, Adam Levine. The rumors initially surfaced in 2004 when Simpson was still married, but they went unaddressed at the time. According to an eyewitness referenced by Distractify, and initially reported by Dazzling News, Levine and Simpson were seen getting handsy with one another at a Los Angeles club. 

"It was obvious that something weird was going on," the unnamed person asserted, adding, "A few days later, Adam was talking about how he and Jessica had 'gotten it on' in the hotel that night." The report coincided with subsequent claims that Levine and Simpson had spent a night together at the infamous Chateau Marmont, with the former reality star allegedly leaving the premises wearing Levine's T-shirt the next morning.

However, during Lachey's 2006 interview with Rolling Stone, the "Where You Are" singer disclosed that Levine had approached him after his divorce from Simpson and openly denied that any cheating had occurred. Lachey recounted, "It was a two-minute conversation. [Levine] said to me, 'Nothing happened while you guys were married.' He looked me in the eyes and said that, so I chose to believe him," (via Live Journal). 

In 2006, Jessica Simpson began a relationship with musician John Mayer, as detailed in her memoir. The two met while she was still married to Nick Lachey, but they didn't start dating until after their divorce was finalized. Mayer and Simpson's relationship was tumultuous, to say the least, as he reportedly broke up with her multiple times. During a 2020 appearance on "Today," Simpson reasoned, "The relationship was very complex. It was always on-again, off-again, on-again, off-again." She added, "And I went back close to nine times," (via X, formerly Twitter). 

After their 2007 breakup, Simpson started dating NFL player Tony Romo, but Mayer remained present in her life due to her sister's marriage to Mayer's friend, Fall Out Boy's Pete Wentz. Simpson recalled in "Open Book" how Mayer would frequently visit her parents' house to stay close to her through his friendship with Wentz. In 2010, Mayer stirred controversy with a Playboy interview where he infamously referred to Simpson as "sexual napalm." 

Mayer said of Simpson, "That girl is like crack cocaine to me," and divulged, "Sexually, [the relationship] was crazy." The "Irresistible" singer, shocked and embarrassed for her family, eventually decided to cut ties with him for good after being messed around too much. In her book, she confirmed, "I erased his number. He made it easy for me to walk away." Simpson later told Oprah.com that Mayer had apologized but she wasn't interested in accepting it.

Following her split from John Mayer, Jessica Simpson dated former NFL player Tony Romo. In a 2008 interview with Glamour, the star recalled how she first became aware of Romo through a TV report about her being his celebrity crush. However, this happened during Simpson's divorce from Nick Lachey, and she didn't meet the athlete until a year and a half later. On their first date, the couple had their first kiss within 10 minutes.

Simpson and Romo's tumultuous romance became a media sensation, with tabloid headlines intensifying, particularly after the Dallas Cowboys, Romo's team, lost to the Philadelphia Eagles in a December 2007 game. Simpson, who wore a pink jersey at the match, faced criticism from Cowboys fans who accused her of distracting Romo. Despite the public scrutiny, Simpson emphasized in a 2009 Vanity Fair interview that they didn't let it impact their relationship. 

"If we did, we wouldn't be together," the singer shrugged. However, Romo ended the relationship later that same year. In "Open Book," Simpson divulged that Romo believed she had cheated on him with John Mayer, explaining that she ran into the singer-songwriter at her parents' house but that nothing had happened. Unfortunately, as she didn't tell Romo about the encounter, he doubted her explanation and decided to end their relationship on her 29th birthday.