A little over a year ago, Jessica Simpson openly hinted that she had developed a taste for younger men, telling reporters on the red carpet: “I think I’m into younger men at the moment.”
The newly single star, then 45, made the playful admission at the premiere of All’s Fair—her first acting role in 15 years—nine months after separating from her husband of a decade, Eric Johnson.
“When you’re newly separated… I feel like younger guys kind of like the confidence of an older woman, I’m discovering,” she joked.
By April, it appeared she had brought that idea to life, as she was seen growing close to musician Thomas Eisenhood, who is 13 years younger than her.
The age difference attracted attention, but so did the timing.
The former pop superstar had largely disappeared from the spotlight. Her career had slowed, her marriage had fallen apart and she was adjusting to life as a single mother of three while maintaining her sobriety.
Jessica Simpson is experiencing a career renaissance, while her romance with younger musician Thomas Eisenhood has also lifted her spirits, according to an insider who spoke to Our News Outlet (Jessica Simpson pictured in October 2025)
“They have been dating all year, but have grown even closer this fall as they make holiday plans together,” the insider said of Simpson, 46, and Eisenhood, 33 (pictured above) (Source: Thomas Eisenhood/Facebook)
Now Simpson is intent on reshaping her life, and 33-year-old Eisenhood appears to be part of that new chapter.
At 46, she is said to be enjoying “a new, sexier phase of her life” and is unfazed by the age gap because Eisenhood “can keep up with her energy,” an insider told Our News Outlet. “She is a real powerhouse who never sits still.”
The source insisted this is more than a brief romance, adding: “They have been dating all year, but this fall they have gotten even closer as they make holiday plans together.”
The pair finally made a public appearance in early October, exchanging flirtatious looks and taking selfies at Albuquerque’s Balloon Fiesta Park.
For the most part, however, they have kept the relationship private. Neither has shared romantic Instagram photographs, although attentive fans have noticed Simpson liking his posts.
Away from the cameras, the Texas-raised singer is reportedly captivated by Eisenhood’s Southern manners.
“Tom is a true gentleman from Nashville who really looks out for her,” the insider said.
“It’s all ‘yes ma’am’ and old-school manners as he guides her musically. He is so skilled and great with a melody, and she loves that he can contribute to her musical dreams.”
His arrival may have come at an especially significant time, as Simpson works to reconnect with her musical beginnings.
“Tom is a true gentleman from Nashville who really looks out for her,” the insider said (Source: Thomas Eisenhood/Facebook)
Her journey back to music has been a lengthy one.
At the height of her fame, the Irresistible singer was one of pop’s biggest stars, while MTV’s Newlyweds made her a household name in the early 2000s.
But her music career eventually went quiet. She had not released a single in 17 years, turning instead from the charts to her namesake fashion business, which is now sold exclusively through Walmart.
Then came an unexpected return last year with the release of her Nashville Canyon EPs, Part 1 and Part 2.
This time, though, there was no major record label backing her. Simpson released the projects independently and spoke proudly about that decision at the MTV VMAs in September 2025: “It’s crazy to be here and to not have a record label and to be here representing myself for myself. It’s really empowering.”
She also returned to live performance after a 15-year absence, beginning with an appearance at the Luck Reunion festival in Texas, where she told the audience: “I am now a very single lady.”
The comeback has so far been modest rather than stadium-sized. Her 2026 tour consisted of only seven summer dates, most of them at casinos, including Hard Rock Live in Oklahoma and Yaamava’ Resort in California.
Her acting comeback was similarly brief. Her appearance in Ryan Murphy’s Hulu legal drama All’s Fair lasted for a single guest episode, during which she spent six hours in prosthetics portraying a woman left with botched plastic surgery.
“She is completely inspired, and I think Tom has something to do with that because he makes her feel sexy and alive,” the insider said (Simpson pictured in July 2026) (Source: Jessica Simpson/Instagram)
“Jessica and Tom speak the same language because they are both musicians and they both have a sexy, quirky sense of humor,” the insider said, adding: “She calls him ‘saxy’” (Source: Thomas Eisenhood/Facebook)
Simpson has also spoken candidly about the self-doubt she carried, telling an audience at Foxwoods casino last December that she never felt “good enough” as a pop star in the 2000s.
In June, she reflected on Instagram on what her years away from performing had cost her.
“Over the last 15yrs of not performing, I haven’t been able to fully express myself in ways that make the most sense for my life,” she wrote.
She thanked fans for helping her regain her confidence onstage, writing: “Each and every single one of you that bless my heart by comin’ to MY HOME on the stage have become a major part of my journey through the pain and the joy. Thank y’all for making me feel loved and valued.”
It appears her latest romance may also be inspiring her creatively.
“Jessica is very motivated by her music these days,” the insider said. “She is completely inspired, and I think Tom has something to do with that because he makes her feel sexy and alive.”
The couple have even developed a playful nickname for him.
“Jessica and Tom speak the same language because they are both musicians and they both have a sexy, quirky sense of humor,” the source said. “He is really good at playing the saxophone and she calls him ‘saxy.’”
“Jessica’s sister Ashlee really likes Tom,” the insider said (pictured together in 2024)
The nickname is rooted in his musical background. Eisenhood played baritone saxophone for 11 years with the New Orleans band Stoop Kids, which went on indefinite hiatus in 2023.
Since then, he has worked behind the scenes in Nashville as a sound engineer and tour manager, and reportedly joined Simpson on tour intermittently this year.
Their shared love of music marks a sharp contrast with Simpson’s marriage.
“Her ex Eric [Johnson] didn’t really understand her passion for music, but Tom does,” the insider said.
Johnson came from a very different world. The Yale-educated former NFL tight end played for the San Francisco 49ers and New Orleans Saints before meeting Simpson in 2010. He proposed that November, and the couple married in July 2014.
Together, they have three children: Maxwell, 14, Ace, 13, and Birdie, seven.
In January 2025, Simpson confirmed that they were “living separately navigating a painful situation in our marriage,” while emphasizing: “Our children come first.”
She later suggested that a major discovery had shaken her, telling fans she had needed to “ask some very personal questions on the home front” and that she found “my world had been turned upside down.”
Simpson and Eric Johnson divorced in January 2025 after 10 years of marriage. They share three children: Maxwell, 14, Ace, 13, and Birdie, seven (pictured in 2022)
Nearly two years later, the former couple have yet to finalize their divorce. They have continued to maintain a civil relationship for their children and reunited for Ace’s sixth-grade graduation in June.
Simpson, of course, has experienced her share of high-profile relationships.
She married 98 Degrees singer Nick Lachey in 2002, with their relationship documented on MTV’s Newlyweds before they divorced in 2006. She later dated John Mayer, who infamously described her as “sexual napalm,” as well as Dallas Cowboys quarterback Tony Romo.
Her former partners may now have another reason to pay attention.
Simpson is set to reveal more of her story in a Netflix documentary scheduled for next year. The streamer says she has “invited the cameras back in to tell all” for the first time since Newlyweds.
Insiders have suggested the project could be explosive. One source told InTouch: “There’s no telling what she’s going to say about her breakup with Eric in the documentary. It was very messy.” Regarding Lachey, the source added: “Of course Nick is nervous.”
Simpson has strong support from her family, particularly when it comes to Eisenhood.
“Jessica’s sister Ashlee really likes Tom, and so does Ashlee’s husband Evan [Ross]. They all hang out together and talk music because Ashlee and Evan are also musicians,” the source said.
Simpson is set to reveal more in a Netflix documentary due next year, marking her first on-camera account of her life since Newlyweds with former husband Nick Lachey (pictured together in 2004)
Throughout the upheaval, Simpson has remained committed to her sobriety.
She stopped drinking on November 1, 2017, after realizing she had become “somebody that I was afraid of.” She later detailed her struggles in her 2020 memoir, Open Book.
After marking eight years sober on Instagram last year with the words “Today I am clear,” she released her sobriety anthem, Give It All Away, in June. “I’m just a work in progress… and I’m very proud of myself,” she told fans.
This year, she appeared to keep her nine-year sobriety milestone private.
Her transformation has extended beyond music and sobriety, with a noticeable change in her appearance as well.
Last month, Simpson shared a series of striking lingerie photographs for her fashion line. Days later, she revealed a dramatic change in hairstyle, replacing her signature blonde hair with a chocolate-brown brunette shade.
According to the source, the changes form part of “a major glow-up” supported by a detox, daily exercise and a strict skincare routine, as Simpson is “heading toward 50 and wants to stay young looking.”
Most importantly, Simpson now feels she is making her own decisions.
“Jessica used to be so controlled in her career—she was told what to do—but now she is in control and decides what she wants to do,” the insider said.
“She wanted to give up reality TV and acting to return to her music career, so that is what she did. She is proud of how far she has come.”
That vision appears to include a prominent role for Eisenhood.
“Next year she will be touring more because she loves performing in front of a live audience,” the insider said. “It thrills her, and she will take Tom with her.”
Our News Outlet has contacted representatives for Simpson for comment.
