Hilary Duff and Joel Madden: A Look Back at Their Relationship

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In July 2004, 25-year-old Joel Rueben Madden began dating teen idol Hilary Duff, who was 16 then. This came a year after she had ended her relationship with Aaron Carter.

Hilary Duff and her boyfriend Joel Madden of Good Charlotte during the 2005 MTV Video Music AwardsHilary Duff and her boyfriend Joel Madden of Good Charlotte during the 2005 MTV Video Music Awards (Credit: WENN / Nikki Nelson / David Livingston)

Private Yet Revealing

Hilary Duff dated Good Charlotte rocker Joel Madden from 16 until 19. Though she has kept details of their relationship private, she implied in an April 2015 issue of Cosmopolitan magazine that he was the first person she had sex with.

“I had a 26-year-old boyfriend,” Duff said in the interview. “So everyone can make their own assumptions about what I was doing.”

“I’ve enjoyed myself. I think everyone should have something where you know it’s not exactly what you’re looking for but you just have a wicked good time. That was freeing for me and a bit of an awakening. It’s fun to have a secret.”

Hilary Duff and Joel Madden had a high-profile relationship from 2004 to 2006, starting when she was 16 and he was 25 Hilary Duff and Joel Madden had a high-profile relationship from 2004 to 2006, starting when she was 16 and he was 25 (Credit: Darrell Graham / Startraksphoto)

Reflecting on the Past

Joel Madden, born on March 11, 1979, in Waldorf, Maryland, is nine years older than Hilary Duff, born on September 28, 1987, in Houston, Texas. They broke up in November 2006.

“I kind of ignored it and tried to just continue to live my life,” Madden told People about their breakup in March 2007.

“People can say or think whatever they want …so in my reality, it’s kind of irrelevant. I’m always the kind of person that does the right thing and keeps my side of the street clean.”

Hilary Duff and Joel Madden during Hilary Duff's 18th birthday partyHilary Duff and Joel Madden during Hilary Duff’s 18th birthday party (Credit: WENN / Nikki Nelson / David Livingston)

Coping with Loss

Hilary Duff was seen in January 2016 putting on a brave face while arriving at AOL Build in New York City following the passing of her French bulldog, Beau.

The then-28-year-old actress was “shattered in a million pieces” over the passing of her dog. Still, she continued her promotional duties for the second season of her comedy-drama TV series, “Younger.”

Hilary Duff expressed her heartbreak on Instagram over the passing of her French bulldog, BeauHilary Duff expressed her heartbreak on Instagram over the passing of her French bulldog, Beau – posted on Instagram on January 12, 2016 (Credit: Hilary Duff’s Instagram)

Promoting the latest season of Younger in January 2016, the Lizzie McGuire actress put her curves on display in a sexy fitted red sleeveless dress by Alexander Wang.

Hilary Duff wears her blonde hair down as she arrives at AOL Build in New York CityHilary Duff wears her blonde hair down as she arrives at AOL Build in New York City on January 13, 2016 (Credit: WENN / Nikki Nelson / David Livingston)

It featured a sexy zip detail on her stomach that goes around the back and down on the left side and a thigh-high slit that showed off her toned leg.

Hilary Duff stuns in a fitted red dress from Alexander WangHilary Duff stuns in a fitted red dress from Alexander Wang (Credit: WENN / Nikki Nelson / David Livingston)

For added glamour, she draped a white Camilla and Marc trench coat over her shoulders and elongated her legs with nude heels.

Hilary Duff finishes her AOL Build ensemble with a white trench coat from Camilla and MarcHilary Duff finishes her AOL Build ensemble with a white trench coat from Camilla and Marc (Credit: WENN / Nikki Nelson / David Livingston)

She wore her short blonde locks in tousled waves, complemented by smoky eye shadow and a slick of vampy red lipstick.

Hilary Duff's feet in nude Brian Atwood sandalsHilary Duff’s feet in nude Brian Atwood sandals (Credit: WENN / Nikki Nelson / David Livingston)

Hilary wore the “Tamara” sandals from Brian Atwood’s Spring 2014 collection. They are made of nude patent leather, feature crisscross ankle straps, and have about 3.5-inch heels.

Hilary Duff's feet in strappy "Tamara" sandals Hilary Duff’s feet in strappy “Tamara” sandals (Credit: WENN / Nikki Nelson / David Livingston)

We can no longer find these sandals online. Below is the pink patent leather version, which has also sold out.

Brian Atwood Pink Tamy Patent Leather Strappy SandalsBrian Atwood Pink Tamy Patent Leather Strappy Sandals, $725