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 job 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 those words into practice, growing close to musician Thomas Eisenhood, who is 13 years her junior.
The age difference attracted attention, as did the timing of the relationship.
The former pop powerhouse had spent years largely out of the spotlight. Her music career had slowed, her marriage had unraveled and she was adjusting to life as a single mother of three while maintaining her sobriety.
Jessica Simpson is experiencing a renaissance, and one insider told the Daily Mail that her relationship with Thomas Eisenhood has given her an added boost (Jessica Simpson 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 (above) (Source: Thomas Eisenhood/Facebook)
Simpson is intent on reshaping her life, and Eisenhood, 33, appears to be part of that fresh chapter.
Now 46, the singer is said to be enjoying “a new, sexier phase of her life” and has no qualms about their age gap because he can match her energy, according to an insider who spoke to the Daily Mail. “She is a real powerhouse who never sits still,” the source added.
The romance also appears more serious 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 made a public appearance together in early October, exchanging flirtatious looks and taking selfies at Albuquerque’s Balloon Fiesta Park.
For the most part, however, they have kept their relationship private. They have not shared romantic photos on Instagram, though observant fans have noticed Simpson liking some of Eisenhood’s posts.
Away from the cameras, the Texas-raised star is reportedly 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 as he guides her musically because he is so skilled, he is great with a melody, and she loves that he can add to her musical dreams.”
Eisenhood may also have entered her life at an important moment, 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)
Her journey back to music has been a lengthy one.
At the height of her fame, the Irresistible hitmaker was one of pop’s biggest stars. MTV’s Newlyweds later made her a household name in the early 2000s.
But new music gradually disappeared from her schedule. 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 musical return last year with her two Nashville Canyon EPs, Part 1 and Part 2.
This time, however, there was no major record label supporting the project. Simpson released the music 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 performances after a 15-year absence, beginning with the Luck Reunion festival in Texas, where she told the audience: “I am now a very single lady.”
The comeback has nevertheless been modest in scale. Her 2026 tour consisted of a seven-date summer run, with most performances taking place at casinos, including Hard Rock Live in Oklahoma and Yaamava’ Resort in California.
Her return to acting was brief as well. Her role in All’s Fair was limited to one guest episode of Ryan Murphy’s Hulu legal drama, during which she spent six hours in prosthetics to portray a woman whose plastic surgery had gone badly wrong.
“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 openly about her struggles with confidence, admitting during a performance 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 long break from performing had taken from 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 supporters with helping her regain 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.”
Her latest inspiration may be close by.
“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 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 insider 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)
Eisenhood has serious musical credentials. He played baritone saxophone with the New Orleans band Stoop Kids for 11 years, until the group went on indefinite hiatus in 2023.
He has since worked behind the scenes in Nashville as a sound engineer and tour manager, and has reportedly joined Simpson on tour at various points 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 later that year, and they married in July 2014.
The couple have three children: Maxwell, 14, Ace, 13, and Birdie, seven.
In January 2025, Simpson confirmed that they had been “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 split, 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 and 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 remained amicable for their children and reunited in June for Ace’s sixth-grade graduation.
Simpson has never been a stranger to headline-making 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 controversially 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 revisit her past 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.
Insiders have hinted that the project 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’s family, meanwhile, appears supportive of her new relationship.
“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 open up in a Netflix documentary due next year, marking her first on-camera account of her life since Newlyweds with ex-husband Nick Lachey (pictured together in 2004)
Through all the changes, 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 of sobriety on Instagram last year with the words “Today I am clear,” she released her sobriety anthem Give It All Away in June, telling fans: “I’m just a work in progress… and I’m very proud of myself.”
This year, she appeared to keep her nine-year sobriety milestone private.
Her transformation extends beyond music and sobriety, with a physical makeover also attracting attention.
Last month, Simpson shared a series of lingerie photos promoting her fashion line. Days later, she unveiled a dramatic change, replacing her signature blonde hair with a chocolate-brown brunette style.
The source described the changes as part of “a major glow-up” supported by a detox, daily exercise and a strict skincare routine, adding that Simpson is “heading toward 50 and wants to stay young looking.”
Most importantly, Simpson now appears to be directing her own career.
“Jessica used to be so controlled in her career, she was told what to do, but now she is in control and she decides what she wants to do,” the insider said.
“She wanted to give up reality TV and acting to go back 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 her plans for the future.
“Next year she will be touring more as 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.