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Millennials that grew up with Hilary Duff don't just remember her generation-defining projects and style, we remember her first loves and heartbreaks like they were our own. Honestly, it was hard enough to separate Duff from Lizzie McGuire without witnessing her on-screen kiss with late heartthrob Aaron Carter spark a real-life teen romance in the early 2000s.
Over 20 years later, many of the girls who saw themselves in a 13-year-old Duff continue to relate to her as a 38-year-old married mom of four children. Duff shares three daughters with current husband Matthew Koma, as well as a 13-year-old son with her ex-husband, Mike Comrie.
With a brand new album on the horizon, Duff is entering a new era while reflecting on her past. As the pop star embarks on her first tour in over a decade to celebrate the release of her sixth studio album Luck…or Something, now feels like the perfect time to blast “Come Clean” and take a walk down memory lane.
Here's a rundown of Duff's current and former relationships, starting at the present and working our way back to the year 2000.
Hilary Duff and Matthew Koma (2017—Present)
Koma immediately emailed a friend that he wanted to marry the pop star after meeting Duff at a business meeting in 2015. He got closer to his goal in 2017, though their relationship involved a series of stops and starts before welcoming their first daughter, Banks Violet Bair, in October 2018. Since their intimate wedding in December 2019, Duff and Koma have welcomed two more daughters, Mae James and Townes Meadow.
Outside of the home, Koma is the main producer of Duff's sixth studio album, Luck… or Something, as well as a co-writer on her singles, “Mature” and “Roommates."
Hilary Duff and Matthew Koma first met at a business meeting in 2015, and it was (mostly) on from there.
Hilary Duff and Jason Walsh (2016)
After working out at the Jason Walsh's private training studio for at least two years, Duff hard-launched her relationship with her personal trainer with a black and white PDA photo in October 2016. Though the pair reportedly split just over a month later, Duff said they were together for “a while” before they went public. "People don't know the ins and outs of everything," she revealed in Cosmopolitan's February 2017 issue, per E! News. “It was definitely my first more serious relationship since my ex-husband.”
Hilary Duff and Mike Comrie (2007—2014)
According to E! News, Duff began dating former NHL player Mike Comrie in 2007, while he was still playing hockey with the New York Islanders. The power couple wed in 2010 and welcomed their son Luca in 2012. The pair announced their amicable separation in 2014 and finalized their divorce in 2016.
"We are constantly seen together and everyone's like, 'What are they doing? Are they back together, are they not?'" Duff told Giuliana Rancic in 2014. “We are really good friends and we have so much respect for each other, and, obviously, Luca is our number one priority.”
Hilary Duff and Joel Madden (2004—2006)
At 16 years old, Hilary Duff began dating 25-year-old Good Charlotte's frontman Joel Madden. The relationship spanned two year, with fans speculating that the age-gap inspired her recent single, “Mature." Among many lyrics about a former partner and their new, younger girlfriend, Duff sings, "She looks like she could be your daughter, like me before I got smarter. When I was flattered to hear you say, 'You're so mature for your age, babe.'”
“Mature’ is a little conversation that my present self is having with my younger self,” Duff revealed in a press release, per People. "The two of us are reflecting on a past experience and sending love to each other. It’s a chuckle, a wink, and a sense of being grateful that we are sure footed in where we landed.”
Despite fan speculation about the somewhat scathing lyrics, Duff told Vogue it's about a “brief experience” she had “a long, long time ago,” but that it's“not totally autobiographical.” She continued, "I took a few artistic liberties just to make the song work structurally, but the gist is the gist. I was looking back on this relationship and thinking about whether this guy had a habit of dating younger women or whether I was ‘special.’ The whole experience was super therapeutic to write about, but being so vulnerable through your music can be really scary.”
Duff continues to maintain a strong, supportive friendship with Nicole Richie, who began dating Madden after his split from Duff in 2006. The pair have been married since 2010 and share two children.
Hilary Duff and Frankie Muniz (2002)
Muniz recently revealed he dated Hilary Duff for a brief period in 2002, but stopped speaking to his former costar immediately after shooting Agent Cody Banks. "I've never talked to Hillary since the last day of filming. I've not said one word to her since then," Muniz said on the on the Joe Vulpis Podcast in October 2025, per E! News. “There was a small dating element at the time. So there was also that element that wasn't happening anymore, so, it was awkward because of that.”
Apparently, things went a bit sour before they even made it to set. According to Muniz, he was guest starring on Lizzie McGuire when he told Duff's mom about the spy movie. Though Muniz said his contract gave him a say in his costar, Duff's mom went behind his back and got her daughter cast in the film without his imput. "Her mom's like, 'Guess what? We're going to be spending the summer together,'" Muniz said, adding that he “wasn't mad” but “wasn't thrilled about it.”
Hilary Duff and Aaron Carter (2000—2003)
Duff famously dated the late Aaron Carter on-and-off from 2000 to 2003, reportedly getting together around the time he filmed Lizzie McGuire's iconic Christmas episode, “Here Comes Aaron Carter.” The young teens split for good in 2003, though Carter later referred to Duff as the “love of his life” in a series of tweets in 2014.
In April 2023, Duff penned a heartfelt tribute to the rapper after his tragic death at 34 years old. “I’m deeply sorry that life was so hard for you and that you had to struggle in front of the whole world,” Duff wrote on Instagram. “You had a charm that was absolutely effervescent… Boy, did my teenage self love you deeply. Sending love to your family at this time.”
