We stirred up quite a buzz online when we revealed about Nicole Richie and Joel Madden that The Good Charlotte rocker used to date Hilary Duff when she was just 16 and he was 24. That little piece of information alone set off all sorts of alarm bells for us, and we haven’t been able to ignore it since.
We’ve also added some juicy details about her relationship with the late Aaron Carter.
We love a good backstory, so let’s rewind to September 28, 1987. Hilary Duff was born in Houston, Texas, the youngest child of Bob and Susan Duff. Around 1993, Hilary, her sister Haley, and their mom moved to Los Angeles so the girls could pursue acting careers. Their dad, Bob, stayed in Houston to manage things at home. But maintaining the family home wasn’t the only thing he was doing, and we’ll get into that soon.
So anyway, when Hilary Duff was thirteen, she landed her breakout role as the main character in the Disney Channel series Lizzie McGuire. Around that time, she was dating Aaron Carter. They had the typical teenage romance—holding hands, hugging, going to the movies, and sharing the occasional kiss. Later on, Aaron implied in his memoir that he was Hilary’s first, but Hilary quickly shut that down, calling it a big old lie. Eventually, Aaron dumped her for Lindsay Lohan, then broke up with Lindsay to get back with Hilary, and then cheated on Hilary with her best friend. After that, Hilary moved on.
In 2004, when Hilary was 16, she met 24-year-old Joel Madden through a mutual friend. “We were friends for like three months before we even…” she said. Oh, so you were pals first? That’s nice. Hilary told Teen Vogue that Joel was the most respectful boyfriend she’d ever had. She added, “We had five or six dates before we even kissed.” Joel mentioned that it was the slowest relationship he’d ever been in terms of getting physical, but he liked how things grew organically between them.
Now, you’re probably wondering what Hilary’s parents thought about all this. “How did your parents react? You’re almost 18, you’re still 17, right?” someone asked. “Um, well, they reacted, you know,” she replied. And what did she mean by “reacted”? If it didn’t involve a butt whooping, we have no idea. Hilary said that eventually, her parents were happy she was in a relationship with Joel.
For many child stars, becoming the family’s primary earner can create a lot of stress and tension, especially when the parents rely heavily on their income. Demi Lovato has spoken out about how this role reversal caused friction within her family. But Hilary Duff’s situation was a bit different because her parents had their own money; her dad owned several businesses in Houston. So why didn’t her parents step in and tell Joel Madden to stay away from their daughter? Maybe because they were too wrapped up in their own messy relationship.
You might remember that Hilary, her mom, and her sister moved to Los Angeles while her dad stayed back in Houston. It turns out he was living recklessly there. He admitted to Inside Edition that he was unfaithful to Hilary’s mom, and the combination of his affair and the physical distance between them led to their marriage falling apart. They decided to get divorced around 2005, but the proceedings dragged on for over two years. At one point, Hilary’s dad was even jailed for ten days for selling over $300,000 worth of stocks without court approval. When the divorce was finally settled, Hilary’s mom received a substantial amount of money.
As for Hilary and Joel, they tried to keep their relationship under the radar. It wasn’t too hard since Joel preferred staying in and watching TV. Hilary told the Love Bomb podcast that their relationship was intense and consumed her life, taking up every minute of her day. But this wasn’t the only thing that overwhelmed her. She later shared with Health magazine that when she was 17, she was just 5’2″ and weighed only 98 pounds. She became obsessed with her diet and exercise, which led to serious health issues, including frequent hand cramps due to a lack of proper nutrition. The constant pressure to maintain a certain look, despite her naturally athletic build, wreaked havoc on her health.
Hilary was young, impressionable, in the spotlight, struggling with body image issues, and secretly dating an older man. Just two months before turning 18, she publicly revealed her relationship with Joel, finally lifting some weight off her shoulders. Once they went public, Joel played a bigger role in her career. He appeared in her 2006 movie “Material Girls” and influenced many songs on her 2007 album “Dignity.” Surprisingly, Joel wasn’t criticized for their age difference; instead, the industry embraced their relationship. They even posed together on the cover of Teen People magazine and gave a joint interview about their relationship. Joel mentioned enjoying time with Hilary’s mom, even when Hilary couldn’t join them. The article highlighted Joel’s respectful nature, always covering Hilary when she bent over in her low-rise jeans, and credited her with helping him become more social. Joel dismissed criticism about dating a teenager, saying, “I didn’t care what the press would say. I cared what my mom would say.” They insisted they shared the same maturity level, with Joel claiming Hilary was wise beyond her years. They felt comfortable together but were in no hurry to get engaged. The journalist noted, “Still, Madden let it slip that if he had a daughter Hilary’s age, he wouldn’t let her date a guy his age.”
In a later interview with Cosmopolitan, Hilary commented on her first time, saying, “Everyone already knew I had a 26-year-old boyfriend, so everyone can make their own assumptions about what I was doing.”
Once they went public, cracks in their relationship began to show. During an interview with Elle magazine, Hilary described Joel’s hometown of Waldorf, Maryland, as “pretty ghetto,” sparking outrage. Residents, particularly from the predominantly black community, felt there were racial undertones to her comment. Hilary was forced to deny the statement through her representative, claiming she never said those words. As backlash grew, she fired her rep and hired a new publicist, who insisted her comments were taken out of context. The new statement clarified that Hilary referred to an apartment complex Joel once lived in, not the entire city of Waldorf.
In November 2006, about a year after they went public with their relationship, 19-year-old Hilary and 27-year-old Joel broke up. Actually, to be more accurate, Hilary dumped him. Imagine being nearly 30 and getting dumped by a teenager. Ouch. Just a month later, Joel was dating Nicole Richie, and you can find all the juicy details about their relationship in the video linked in the description box.
While Joel quickly moved on with a relationship that’s still going strong today, Hilary struggled with the breakup. She told E! News that it was one of the hardest things she had ever gone through, and she felt like a wreck for the next year and a half. She really didn’t enjoy being single. To make matters worse, she constantly saw photos of Joel and Nicole partying all over Hollywood. Hilary was shocked by how much he had changed. She told Seventeen magazine, “All the going out he did after we broke up shocked me. That was so out of character for him. When we were together, he hated stuff like that. So I felt like I didn’t really know him as well as I thought I did.”
Um, Hilary, maybe Joel stayed home when he was with you because you weren’t old enough to get into the clubs. No shade, but… yeah. Eventually, Hilary found love again when she married hockey player Mike Comrie in 2010. They had a son in 2012 but announced their separation in 2014. And as soon as the news of their split hit the web, guess who came creeping back? Aaron.
After retweeting a glamorous photo of Hilary, Aaron tweeted, “Don’t be that stupid douche who loses the love of your life forever like me.” He continued, “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. It is what it is, and I wish her the best of luck. She knows I’ll always love her.”
Hilary admitted that Aaron’s public declaration made her feel a bit uncomfortable, especially since she was still legally married at the time. Ultimately, she wasn’t interested in rekindling things with Aaron. Tragically, on November 5, 2022, Aaron passed away at the age of 34. Hilary shared her feelings in an Instagram post, writing, “You had a charm that was absolutely effervescent. Boy, did my teenage self love you deeply.”
In 2015, Hilary began dating singer and songwriter Matthew Koma. After a few ups and downs, they married in 2019 and now share two children. In February 2022, Hilary and Matthew were spotted on a group date with Joel and Nicole. Later, during a Vanity Fair lie detector test, Hilary was asked if staying friends with her exes was important. She replied, “I do enjoy being friends with him now, 100%, but I don’t need to be friends with all my exes.”
So there you have it. Hollywood remains as strange as ever, with Hilary and Joel’s unconventional relationship being just one example of the industry’s many overlooked romances. If you enjoyed this video, follow us on TikTok for more content like daily news updates and mini-documentaries.