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Hilary Duff and Aaron Carter's relationship timeline was complicated.

Hilary Duff & Aaron Carter’s Relationship Timeline Is Bittersweet

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Hilary Duff and Aaron Carter’s tween love story will always be a sweet one. The duo might have dated two whole decades ago, but their relationship is still unforgettable. (A moment for the iconic Christmas-themed Lizzie McGuire episode, “Aaron Carter's Coming to Town.”) Although they didn’t stay in touch in the years after their breakup, they always seemed to have a soft spot for one another.

After Carter passed away on Nov. 5, Duff took to Instagram to share her condolences. Despite all the time that has passed since they dated, Duff had super kind words to say. “For Aaron- I’m deeply sorry that life was so hard for you and that you had to struggle in front of the whole world,” she wrote. “You had a charm that was absolutely effervescent... boy did my teenage self love you deeply. Sending love to your family at this time. Rest easy.”

As we mourn Carter’s life, here’s a look back on his adorable relationship with Duff.

December 7, 2000: Hilary & Aaron Started Dating
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“I started dating Hilary on my 13th birthday,” Carter said during a 2005 appearance on The Big Idea With Donny Deutsch. “I was dating her for like a year-and-a-half, then I just got a little bored so I went and I started getting to know Lindsay [Lohan], dating Lindsay.”

Duff’s 2002 song “Haters” was even rumored to be about her love triangle with Lohan. However, by 2007, any drama seemed to be quashed. “We are both adults and whatever happened, happened when we were young,” Duff told People at the time. “It’s over.”

March 2001: Aaron Appeared On Lizzie McGuire
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In March 2001, Carter made a guest appearance on Lizzie McGuire. In the show, Carter appeared as himself, and Lizzie eagerly crashed her celebrity crush’s music video shoot. Spoiler alert: At the end of the episode, Carter kissed Lizzie under a mistletoe, making it the perfect Disney episode, like, ever.

2003: They Broke Up
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Despite their brief breakup when Carter dated Lohan, he and Duff eventually got back together, but their reconciliation didn’t last. In his 2005 interview with Donny Deutsch, Carter admitted to cheating on Duff. “I ended up cheating on Hilary with her best friend. That's nothing to smile about,” he said. "She really got her heart broken from me and I'm sorry for that."

March 2014: Aaron Tweeted About Hilary
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In March 2014, Carter brought up his ex on Twitter, retweeting a photo of her. "Don't be that stupid douche that loses the love of your life forever.. Like me,” he wrote. "I'll spend the rest of my life trying to better myself to get back to her. I don't care what ANY of you think."

In April, he doubled down on the same message. Per the Daily Mail, Carter told Entertainment Tonight, “I don't know who she is today, she doesn't know who I am today, but I would sweep her off her feet if I ever got a chance to again and fix what I did wrong.”

March 2015: Hilary Responded To Aaron’s Tweet
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Carter’s romantic tweets didn’t work on Duff, who opened up about the situation to Cosmopolitan in 2015. “Keep it between text messages," she suggested. In 2014, she also talked to Buzzfeed about Carter’s declarations. “I don't know how I feel. I mean, that was so long ago... and we kind of just... don’t know each other.”

November 6, 2022: Hilary Mourned Aaron’s Death

Following reports of Carter’s passing, Duff took to Instagram to grieve her Lizzie McGuire crush. “Boy did my teenage self love you deeply,” she wrote.

Although these tweenage lovebirds never rekindled their romance, it seems like they both had nothing but affection for each other.