A little over a year ago, Jessica Simpson openly embraced the idea of dating 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, she appeared to be putting that theory into practice, growing close to musician Thomas Eisenhood, who is 13 years younger than her.
The age difference attracted attention, as did the timing of the romance.
The former pop sensation had largely stepped away from the spotlight. Her career had slowed, her marriage had fallen apart and she was facing life as a single mother of three while maintaining her sobriety.
Jessica Simpson is enjoying a career renaissance, while her relationship with younger musician Thomas Eisenhood has also lifted her spirits, according to an insider speaking 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)
But Simpson is determined to rebuild her life, and Eisenhood, 33, appears to be part of that new chapter.
Now 46, she is reportedly enjoying “a new, sexier phase of her life” and feels comfortable with their age gap because “he can keep up with her energy,” an insider told Our News Outlet. “She is a real powerhouse who never sits still.”
The relationship also appears to be more than a brief fling. “They have been dating all year, but this fall have gotten even closer as they are making holiday plans together,” the source said.
The pair finally went public in early October, exchanging flirtatious looks and taking selfies at Albuquerque’s Balloon Fiesta Park.
Beyond that appearance, however, they have kept the relationship private. The couple have not shared romantic photos on Instagram, although observant fans have noticed Simpson liking Eisenhood’s posts.
Away from the cameras, the Texas-raised singer is said to be captivated by his Southern charm.
“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. He guides her musically because he is so skilled and has a real gift for melody, and she loves that he can contribute to her musical ambitions.”
His arrival may have come at an ideal time, as Simpson works to reconnect with her musical identity.
“Tom is a true gentleman from Nashville who really looks out for her,” the insider said (Source: Thomas Eisenhood/Facebook)
The road back to music, however, has been a long one.
At the height of her fame, the Irresistible singer was one of pop’s biggest stars. MTV’s Newlyweds also 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, instead moving from the charts into the boardroom through her fashion brand, which now sells exclusively through Walmart.
Then came an unexpected musical return last year with her Nashville Canyon EPs, Part 1 and Part 2.
This time, there was no major record label supporting the project. Simpson released the records independently and spoke about the experience 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 said.
She also returned to live performance after a 15-year break, beginning with 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 a seven-date summer run, with most shows taking place at casinos, including Hard Rock Live in Oklahoma and Yaamava’ Resort in California.
Her return to acting was similarly brief. Her role in All’s Fair was limited to one guest episode of Ryan Murphy’s Hulu legal drama, for 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 share a sexy, quirky sense of humor,” the insider said, adding: “She calls him ‘saxy’” (Source: Thomas Eisenhood/Facebook)
Simpson has also spoken openly about the doubts she carried during her earlier career. At a Foxwoods casino performance last December, she admitted that she never felt “good enough” as a pop star in the 2000s.
In June, she reflected on Instagram about what her long absence from the stage 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 credited her fans with helping her regain confidence, 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.”
Her new relationship may also be inspiring the creative revival.
“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.”
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The couple have even developed a playful nickname for Eisenhood.
“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 grounded in Eisenhood’s musical background. He 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. He has also reportedly joined Simpson on tour at various points this year.
Their shared musical interests mark a sharp contrast with Simpson’s marriage.
“Her ex Eric [Johnson] didn’t really understand her passion for music, but Tom does,” the insider added.
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.
They share three children: Maxwell, 14, Ace, 13, and Birdie, seven.
In January 2025, however, 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 contributed to the breakdown, telling fans she had needed to “ask some very personal questions on the home front” and that “my world had been turned upside down.”
Simpson and Eric Johnson divorced in January 2025 after 10 years of marriage and share three children: Maxwell, 14, Ace, 13, and Birdie, seven (pictured in 2022)
Almost two years later, the former couple have yet to finalize their divorce. They have nevertheless remained amicable for their children and reunited for Ace’s sixth-grade graduation in June.
Simpson, of course, has never been a stranger to high-profile relationships.
She married 98 Degrees singer Nick Lachey in 2002, with their relationship chronicled on MTV’s Newlyweds before they divorced in 2006. She later dated John Mayer, who famously described her as “sexual napalm,” as well as Dallas Cowboys quarterback Tony Romo.
Her former partners may now be watching closely.
Simpson is set to reveal more in a Netflix documentary scheduled for next year. The streaming service says she has “invited the cameras back in to tell all” for the first time since Newlyweds.
People close to the project have hinted that it could be revealing. 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 also 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 will reveal more in a Netflix documentary due next year, marking her first on-camera account 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.
Simpson’s resurgence has extended beyond music, acting and sobriety. Her physical transformation has also attracted attention.
Last month, she shared a series of striking lingerie photos for her fashion label. Days later, she unveiled another dramatic change, replacing her signature blonde hair with a chocolate-brown style.
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 is now 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.”
Eisenhood is expected to feature in those plans.
“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.”
The Daily Mail has contacted representatives for Simpson for comment.
