It started with a mistletoe kiss. If you grew up in the early 2000s, you remember exactly where you were when Aaron Carter strutted onto the set of Lizzie McGuire. He was the blond "I Want Candy" heartthrob with the frosted tips, and she was the relatable queen of Disney Channel. When they shared that scripted kiss in the 2001 episode "Here Comes Aaron Carter," it wasn't just TV magic. It was the start of a real-life saga that would span two decades, involve an infamous love triangle with Lindsay Lohan, and end in a heartbreaking tribute that still makes fans misty-eyed.
The Relationship Between Hilary Duff and Aaron Carter: More Than Puppy Love?
People often write off teen romances as fleeting or "fake" for the cameras. But for Hilary Duff and Aaron Carter, the connection was intense from the jump. They started dating on Aaron’s 13th birthday in 2000. Think about that for a second. While most of us were struggling through middle school algebra, these two were navigating a high-profile relationship in the glare of the paparazzi.
Aaron later admitted that Hilary was the first girl to ever break his heart. He once told a podcast that she was the only person who actually dumped him, and honestly, that tracks. While Aaron was the wild child of the pop world, Hilary was building a massive empire. They were together on and off for nearly three years, a lifetime in teen years.
The Love Triangle That Defined a Generation
You can't talk about Hilary and Aaron without mentioning the "Redhead in the Room." In 2002, things got messy. Aaron started seeing Lindsay Lohan while he was still technically involved with Hilary.
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"I was dating her for like a year and a half, and then I just got a little bored, so I went and started getting to know Lindsay," Aaron told Donny Deutsch in 2005.
Yeah, he actually said "bored."
It sparked a legendary feud. We saw them crashing each other’s movie premieres—Hilary showing up to the Freaky Friday event and Lindsay returning the favor at the Cheaper by the Dozen party. It was the ultimate Disney vs. Disney showdown. Looking back, it’s kinda wild how much energy the media put into pitting two teenage girls against each other over a boy who, by his own admission, was just messing around.
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Why Aaron Carter Never Truly Let Go
Years passed. Hilary moved on, got married to Mike Comrie, had her son Luca, and eventually found her "happily ever after" with Matthew Koma. But Aaron? He stayed stuck in the past. In 2014, he went on a Twitter spree that went viral for all the wrong reasons. He called Hilary the "love of his life" and vowed to spend the rest of his days winning her back.
It was uncomfortable. Hilary was literally a mother and a wife at the time. When asked about it on Watch What Happens Live, she admitted it was "unpleasant" because she hadn't seen him in years. "I don't know what to say about it," she told Andy Cohen. It was a classic case of one person holding onto a memory while the other had grown into an entirely different human being.
The Final Chapter and That Heartbreaking Tribute
When Aaron Carter passed away in November 2022 at the age of 34, the world waited to see if Hilary would say anything. She did, and it was perfect. She didn't dwell on the drama or the awkward Twitter years. Instead, she spoke directly to the boy she knew at thirteen.
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"You had a charm that was absolutely effervescent," she wrote on Instagram. "Boy, did my teenage self love you deeply."
That single line—"my teenage self love you deeply"—basically summed up why we were all so obsessed. It wasn't about the adults they became; it was about the innocence of that first love. Even Lindsay Lohan "liked" the post, which felt like a quiet end to a twenty-year-old wound.
Actionable Insights for the Nostalgic Fan
If you're feeling a bit sentimental after revisiting this era, here is how you can preserve that 2000s magic without the drama:
- Revisit the Source: You can actually still stream the "Here Comes Aaron Carter" episode on Disney+. It’s Season 1, Episode 7. It’s a total time capsule of 2001 fashion and peak Lizzie.
- Support the Legacy: Aaron’s family has been vocal about mental health and addiction awareness since his passing. If you want to honor his memory, look into organizations like On Our Sleeves, which supports children’s mental health.
- Separate the Art from the Chaos: It’s okay to still love "Aaron's Party" or Metamorphosis. You can appreciate the cultural impact these two had on a generation while acknowledging that their real lives were complicated and often difficult.
The story of Hilary Duff and Aaron Carter is a reminder that child stardom isn't a fairy tale. It’s a high-pressure environment where "puppy love" has real-world consequences. While Hilary found her footing and built a stable, beautiful life, Aaron’s struggle was a public tragedy. Their story remains a definitive chapter of 2000s pop culture because it felt real—messy, beautiful, and ultimately, very human.