The 2000s feature the rise of Disney stars becoming Hollywood icons, which includes Hilary Duff, Lindsay Lohan, and more. Then there is Aaron Carter, who is not exactly a star from Disney but has appeared on their radio airplay alongside Nickelodeon. Once he made a special guest appearance in Lizzie McGuire, he and lead Hilary Duff became a star-studded, yet young couple. But things would not go well for them years later, somewhat becoming enemies.
And due to Aaron's two-timing self, he went to pursue Lindsay Lohan, and for some time, Lindsay would consider Hilary as her enemy. The situation was filled with drama and neither girl truly ended up with Florida-born man.
Here are some little known facts about Aaron Carter's relationship with Hilary Duff and Lindsay Lohan.
12 The Start Of It All
When the new millennium arrived, so did the meeting between Hilary and Aaron. Their relationship was confirmed in 2001 around the latter's 13th birthday. Eventually, Aaron would become a guest star in Hilary's Disney Channel hit show Lizzie McGuire. When the two sang "I Want Candy," the chemistry was there and fans were really into them.
11 Head Over Heels
In the same episode Aaron guest-starred in, the two shared a kiss and while it was definitely acting, we could tell that Hilary was allured during the moment. Considering that the show's writer, Nina Bargiel, worked hard to bring Aaron to the show, it was definitely a highlight in Hilary's career since she was crushing on Aaron.
If it weren't for this episode, their romance would not have sparked and sprinkle events that would eventually happen. While nostalgic, the romance would not age well.
10 Was Supposed To Appear In Another Episode
Due to the positive reception of Aaron Carter's appearance in Lizzie McGuire, he was supposed to appear in another episode, but that never came to be. It would have brought more cute moments between Hilary's character and the show's version of Aaron. But due to working on Seussical, the episode "Welcome Back Carter" was rewritten to have Frankie Muniz appear as himself instead.
9 On-And-Off Issues
Hilary and Aaron's relationship had its ups and downs, but it was more so due to Aaron's carelessness and focus on getting celebrity attention. Even though he cheated on Hilary once, he was given a second chance, only to squash it again.
To say that their relationship was on-and-off would be a total understatement. Being young and in love was definitely a risky time for them as they were still in their teenage years.
8 The Intense Heartbreak
Teenage girls get their unfortunate share of heartbreak after splitting with their partners. Hilary was on the same boat when it was revealed that Aaron had been secretly seeing fellow Disney starlet Lindsay during their on-and-off times and then cheated on her again with another friend. This would be the beginning of a downward spiral for the faithfulness of the rising pop star.
7 He Wanted Her Back, But She Doesn't
Despite being the one responsible for cheating on both Hilary and Lindsay, it was the former who Aaron had tried to reach out many years after their second breakup. He stated on Twitter in 2014 that he would do everything he can for the rest of his life to win Hilary back.
Did it work? Absolutely not. Not only was Hilary wanting to move forward from the tween drama that happened nearly 20 years ago, but she has been with her beloved beau Matthew Koma, getting married to him in 2019.
6 Bragging Rights
Being a teenage heartthrob loved by millions of girls is one thing, but to be a two-timing cheater with a spotlight on you is another. As a young man with ambitious dreams in the music world, Aaron craved the attention outside of his music, so him seeing Lindsay Lohan was the start of the Hollywood mess in the early 2000s.
5 He Got Bored
Talking about being disrespectful to his relationship with Hilary, Aaron somewhat felt sorry for her when asked about dating both her and Lindsay. On a radio show, he confessed his stance on being with both girls.
Aaron proudly claimed on The Big Idea, in regards to dating both Hilary and Lindsay, "I was dating her for like a year-and-a-half and then I just got a little bored so I went and I started getting to know Lindsay, dating Lindsay."
4 Then Drama Hit The Fan
Lindsay did not take things well when she found out that Aaron was also dating Hilary. But instead of attacking Aaron, she instead went for the fellow Disney darling. They went on a quiet, but intriguing red carpet war, showing at each other's movie premieres. And when she made an appearance on SNL, she was standing alongside Rachel Dratch, who dressed up as her and made her overdramatic to the point of being insulting.
3 Too Blunt About Her Looks
Aaron had some nasty comments said about Lindsay when he opted to go back to dating Hilary. On The Big Idea, he said about ending his relationship with Lindsay, "I didn't want to do that anymore, so I got back with Hilary."
The relationship practically meant nothing for Aaron, as Lindsay was just eye candy for him and the media. He might have tried to start anew with Hilary, but he would eat his words while hurting Lindsay in the process.
2 Once A Cheater, Always A Cheater
Even though it was heartbreaking for Hilary to deal with Aaron secretly cheating on her with Lindsay, it can be argued that the Mean Girls star had it worse in this chaotic love triangle. Since he left her for the same girl, it would start a lot of revolutionary events in Hollywood's memorable feuds. Apparently, it was alleged that Lindsay called Hilary's A Cinderella Story costar Chad Michael Murray to spread lies about her.
1 Bringing One Of Hollywood's Iconic Feuds
While the love triangle brought a feud fans will never forget, it is a strangely fond memory to look back on. Despite Aaron backstabbing both of them, Hilary and Lindsay got over him and with time, things managed to calm down.
Funnily enough, when Lindsay began focusing more on music in 2020, she's mentioned on a YouTube live chat that she would be down for Hilary to collaborate with her. Goodbye Aaron, hello Hilary!