Honestly, if you grew up in the early 2000s, Hilary Duff was basically the blueprint for the girl next door. We all watched her navigate the digital halls of Lizzie McGuire, and naturally, we became obsessed with who she was hanging out with when the cameras stopped rolling. It’s been decades since the "I Want Candy" era, yet people are still surprisingly curious about her dating history. Maybe it's because she managed to survive child stardom without the usual Hollywood meltdown, or maybe it's just because her love life has had some truly wild chapters.
From the infamous Disney Channel love triangles to her current "happily ever after" with Matthew Koma, Hilary’s journey hasn’t been a straight line. It’s been messy, high-profile, and at times, a little controversial.
The Aaron Carter and Lindsay Lohan Drama
Before social media existed to track every move, we had the tabloids. And in 2001, nothing was bigger than the triangle involving Hilary Duff, Aaron Carter, and Lindsay Lohan.
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Aaron Carter actually guest-starred on Lizzie McGuire (remember that Christmas episode?), and that’s where the spark started. They began dating on his 13th birthday. It was puppy love, sure, but it lasted for about a year and a half before things got complicated. Aaron famously admitted later that he got "bored" and started seeing Lindsay Lohan while he was still sort of with Hilary.
This sparked a years-long feud between the two teen queens. They were constantly taking shots at each other in the press. Hilary even released a song called "Haters" in 2002 that everyone assumes was about Lindsay. Aaron eventually went back to Hilary, but he later confessed to cheating on her with her best friend. Talk about a middle school nightmare played out on a global stage.
What’s kind of heartbreaking is that Aaron never really seemed to get over her. Even in 2014, he was tweeting about how she was the "love of his life." When he passed away in 2022, Hilary posted a really touching tribute, proving that despite all the teen drama, there was a deep-rooted affection there.
The Joel Madden Years and the Age Gap
If the Aaron Carter stuff was "puppy love," her relationship with Joel Madden was where things got serious—and controversial.
Hilary started dating the Good Charlotte frontman in 2004. At the time, she was 16 and he was 25. People definitely raised eyebrows back then, but in the pre-TikTok era, the discourse wasn't quite as loud as it would be today. They were together for over two years and even collaborated on her Most Wanted album.
They split in 2006, but here’s the kicker: they are actually great friends now. You’ve probably seen the photos of Hilary and her husband, Matthew Koma, going on double dates with Joel and his wife, Nicole Richie. It’s a very "Hollywood" level of maturity that most of us probably couldn't pull off with our exes. Hilary has even said they’re neighbors and hang out all the time.
Marriage #1: Mike Comrie
After a few years of being single and some short-lived rumors (like a brief thing with Frankie Muniz that was never really confirmed as serious), Hilary met NHL player Mike Comrie.
This felt like the "grown-up" phase. They got married in 2010 in Santa Barbara. It looked perfect from the outside. They had a son, Luca, in 2012. But by 2014, they announced they were separating.
The breakup was actually incredibly amicable. There weren't any huge scandals or cheating rumors; they basically just realized the spark was gone. They even went to marriage counseling for over a year before throwing in the towel. They’re still legendary for being the "gold standard" of co-parenting in Hollywood. You’ll still see them at Luca’s soccer games together.
The Personal Trainer and the Brief Break
Between her divorce and her current marriage, there was a bit of a "experimental" phase. She dated her personal trainer, Jason Walsh, for about five months in 2016.
It was her first serious relationship post-divorce. She told Cosmopolitan at the time that she "just needed to make sure it was right" before going public. It didn't last, mostly because he wanted to move to New York and her life was firmly planted in LA.
There was also a very brief summer fling in 2017 with businessman Ely Sandvik. They were caught by paparazzi making out on a beach in Malibu. It was a classic "summer rebound" situation while she was on a break from Matthew Koma (yes, they broke up a few times early on).
Finally, Matthew Koma
Matthew Koma is the one who stuck. They met in 2013 while working on her album Breathe In. Breathe Out. He’s a talented musician and songwriter, and apparently, he has a very specific sense of humor that matches hers perfectly.
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It wasn't an instant "happily ever after," though. They dated, broke up, dated again, broke up again... then finally realized they couldn't stay away from each other. Hilary famously said the "third time's a charm."
They got married in a backyard ceremony in 2019. Since then, they’ve added three daughters to the mix: Banks, Mae, and Townes. Matthew is also a super-involved stepdad to Luca. If you follow him on Instagram, you know he’s basically a professional Hilary Duff fan and a world-class troll (in a funny way).
What We Can Learn From Hilary's Dating History
Hilary’s path shows that your first love—or even your first marriage—doesn't have to be your last. She's navigated some pretty tricky waters, especially considering she grew up in the spotlight.
- Co-parenting is possible: Her relationship with Mike Comrie is proof that you can put your kids first and remain friends with an ex.
- Don't rush the "Forever": She and Matthew Koma took their time, even through breakups, to make sure they were actually right for each other.
- Maturity matters: Being able to hang out with Joel Madden and Nicole Richie shows that time really does heal most wounds.
If you're looking to apply some of Hilary's "success" to your own life, focus on the co-parenting or "ex-friendship" aspect. It requires setting massive ego aside and focusing on the long-term peace of the family. If you're currently going through a split, maybe take a page out of her book: stay quiet, go to counseling if you can, and don't feel pressured to share your "business" until you're ready.