Hilary Duff's Relationship Timeline

Before viewers watched Disney stars like Miley Cyrus on "Hannah Montana" or Selena Gomez on "Wizards of Waverly Place," there was Hilary Duff in "Lizzie McGuire." Duff would go on to lead films like "Cadet Kelly," "Agent Cody Banks," "Cheaper by the Dozen," and "A Cinderella Story." However, she's ventured into darker stuff, too, like 2019's "The Haunting of Sharon Tate," and went back to television with TV Land's "Younger" in 2015 and 2022's "How I Met Your Father." Finally, let's not forget her success in music. Duff has recorded five albums with 2003's "Metamorphosis" selling over five million copies worldwide.

Revisiting Duff's work on the Disney Channel and listening to songs like "Come Clean" and "So Yesterday" are sure to give fans waves of 2000s nostalgia, and the same can be said about looking back at her relationship history. Although Duff has been happily married to Matthew Koma since 2019, the songstress has made headlines for dating pop stars, co-stars, and a much older pop rock band member. Duff's romantic past goes back to when the starlet was 13 years old. Let the romance rumors, marriage details, and longterm relationship stories rain down, because we are coming clean about Hilary Duff's love life.

Young love with Aaron Carter

Aaron Carter found success as a pop musician at an early age. According to Us Weekly, Disney Channel star Hilary Duff began dating the "I Want Candy" singer on his 13th birthday in 2000. Their relationship sparked an infamous feud between Duff and actor Lindsay Lohan. After an on-again, off-again romance with Duff, Carter admitted to also dating Lohan on those off periods of their relationship. 

In a 2005 interview with CNBC (via Us Weekly), Carter revealed, "I was dating [Hilary] 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." Although Carter and Duff got back together, he admitted to cheating on her for the second time. Duff and Carter called it quits in 2003. Long after they went their separate ways, Carter expressed regrets about how things between them played out.

On November 5, 2022, Carter died at the age of 34. After news of his passing broke, Duff posted a tribute to her ex on Instagram. "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."

She went on one date with Shia LaBeouf

Shia LaBeouf and Hilary Duff can thank Disney for their rise to stardom. LaBeouf's first major gig was portraying Louis Stevens on the Disney Channel comedy "Even Stevens" for three seasons in the early '00s, while Duff starred in "Lizzie McGuire" from 2001 to 2004. While both of their beloved shows ended way too soon (presumedly due to the Disney Channel's unofficial 65-episode rule), Duff and LaBeouf were already becoming household names and would continue to find success in movies and television. 

It wasn't until 2011 that LaBeouf revealed that he went on a not-so-pleasant date with Duff in 2002. In the now-defunct Details magazine (via Us Weekly), the "Holes" actor shared that his night out with Duff was "probably the worst date either of us have ever had." LaBeouf didn't go into much detail after that. In 2007, LaBeouf also mentioned a failed date with Rihanna, telling Playboy (via MTV News), "It never got beyond one date. The spark wasn't there. We weren't passionate about each other in that way, so we remain friends." 

Like Duff, the "Transformers" star's dating history also includes Carey Mulligan, Mia Goth, and FKA Twigs. Goth and LaBeouf share a child. In 2020, Twigs filed a lawsuit against LaBeouf, accusing the actor of abuse. He subsequently denied the allegations, but has acknowledged being hurtful in past relationships. The trial is set for April 2023.

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

Whispers of a relationship with Frankie Muniz

While sparks didn't fly between Hilary Duff and Shia LaBeouf, she apparently found a connection with her "Agent Cody Banks" co-star Frankie Muniz. E! News reported that the stars are believed dated between 2002 to 2004. On the flip side, a report from the South Florida Sun Sentinel denies the two were ever a couple.

In 2016, Muniz tweeted a photo of him and Duff on a motorcycle from the pair's time on "Agent Cody Banks." He wrote alongside the picture, "This car took me on my first date, picking up @HilaryDuff. I'm assuming it looked something like this photo! Yes!!!"

Neither Duff nor Muniz have addressed their relationship; however, Duff's husband, Matthew Koma, might have hinted that his wife did have a brief romance with the "Malcolm in the Middle" star. In 2022, the couple took part in an Instagram challenge that asked users to share photos of the early stages of their relationship. Duff jokingly shared a photo of Koma with his ex, Carly Rae Jepsen (the two split in 2016), while Koma got back at his wife by sharing a picture of the "Younger" actor with Muniz, per E! News.

She stayed friends with Jordan Masterson's sister

Whether she dated Frankie Muniz or not, Hilary Duff did go on to date another man in Hollywood. According to Pop Dirt, Duff dated "The 40-Year-Old Virgin" actor Jordan Masterson in 2004, but their romance reportedly only lasted three months.

According to Star magazine (via SF Gate), Duff and Jordan split due to conflicting work schedules. After their breakup she reportedly shared with the mag, "While Jordy is a special person to me, and we're still friends, the timing was just off. My career has to come first right now. I have my priorities straight." The "Cheaper by the Dozen" actor also happens to be friends with Jordan's sister, Alanna Masterson, who is best known for her work in "The Walking Dead" and appeared alongside Duff in the TV series "Younger."

While things didn't work out with Jordan, Duff and Alanna's friendship sure seems strong as ever. Bustle reported that in 2014 Duff and Alanna got matching ghost tattoos with the words "ride or die." What's more, Duff has dedicated IG posts to Alanna, celebrating her birthday in June 2022.

She dated Joel Madden when she was a teenager

Hilary Duff fell for Good Charlotte rocker Joel Madden when she was 16, and their age gap made constant headlines, with the rocker being nine years her senior. In a 2005 interview with "The View," Duff revealed that for some time, she kept their relationship a secret because of their age difference. The two split in 2006 when Duff was 19, per ET

In 2007, Madden told People that he and Duff did not end things on a sour note. "Every girl I've ever dated I have respect for, and I always try to leave them in good terms," he said. That same year, Duff told Ellen DeGeneres that her "Dignity" album included songs that were inspired by their breakup. The rocker went on to date Nicole Ritchie, and the two wed in December 2010. 

In a 2015 interview with Cosmopolitan, Duff did not mention Madden by name but hinted that she lost her virginity to the singer. "I had a 26-year-old boyfriend, so everyone can make their own assumptions about what I was doing." In 2016, she gave a little more insight into her short-lived relationship on "The Love Bomb" podcast. "It was all so encompassing. It was so intense. It was my life," Duff revealed to host and "Younger" co-star Nico Tortorella. In February 2022, Page Six reported that Duff and Madden were spotted grabbing dinner in Los Angeles with their respective spouses, proving that exes can be friendly. 

She married Mike Comrie

Hilary Duff began dating former NHL player Mike Comrie in 2007, and things got serious between the two. The pair got engaged in February 2010 and tied the knot that August. The couple took the next step in their relationship and welcomed a son, Luca Cruz, in March 2012. However, in January 2013, Duff separated from Comrie and pulled the plug on their marriage when she filed for divorce in February 2015, citing irreconcilable differences and asking for primary custody of their son, per TMZ. Her divorce filing came one day after the Daily Mail reported that Comrie was apparently seen drunkenly hitting on women at a Beverly Hills restaurant. 

Duff and Comrie's divorce was settled in January 2016, and the exes agreed on joint custody of Luca. According to TMZ, their divorce documents stated that Duff kept their Beverly Hills home and a mobile home in Malibu, while Comrie kept a couple of luxury vehicles. Duff also had to shell out nearly $2.5 million to her ex-husband.

In 2015, Duff shared with Cosmopolitan that a few factors led to the couple's split, including no longer being in love with one another. "It was a slow set-in of us not being the match that we used to be. I don't want to sound bitter because I'm definitely not, but I don't know if people are meant to be together forever," she admitted. Duff also hinted that getting married at 22 might have also led to their divorce.

Jason Walsh went from trainer to lover

Before her divorce from Mike Comrie was finalized, it was reported that Hilary Duff was dating her personal trainer Jason Walsh sometime in 2015, per People. The "Lizzie McGuire" star made her relationship with Walsh Instagram official in October 2016 when she shared a black and white photo of the two sharing a kiss. (And yes, the picture is still up on her account.) However, Duff confirmed to Cosmopolitan in February 2017 that the pair had broken up in November 2016. A source told People, "They weren't on the same page. He wants to move to New York, but her life is in L.A."

Duff also confirmed to Cosmopolitan that she and Walsh had dated for much longer than what was reported. "We were seeing each other for a while. People don't know the ins and outs of everything. It was definitely my first more serious relationship since my ex-husband," she admitted.

Like many of her past romances, Duff and Walsh appeared to be on good terms after they parted ways. According to E! News, in April 2017, the pair reunited in New York City, where Walsh was training the actor. 

A fling with Ely Sandvik

In January 2017, Hilary Duff was linked to songwriter Matthew Koma, who had previously worked on Duff's 2015 album "Breathe In. Breathe Out." The couple reportedly broke up that March, according to ET. But, of course, Koma would come back into the star's life later on. Before they rekindled their romance, Duff was linked to someone who was not a part of the Hollywood scene.

According to Daily Mail, in July 2017, the actor was photographed having a fun-filled and major PDA outing with businessman and CEO of SOLr Energy Consulting Ely Sandvik on a beach in Malibu. The new couple had no intentions of hiding their infatuation with one another, with Us Weekly sharing photos of the two kissing while out and about in Los Angeles that August. However, their relationship was brief. Perez Hilton suspected that the couple broke up after three months of dating when fans spotted that they had unfollowed each other on Instagram. 

A happily ever after with Matthew Koma

By October 2017, Us Weekly reported that Hilary Duff and musician Matthew Koma were an item yet again. Duff told the women of "The Talk" in December that it was actually the third time they were giving their romance a shot. Duff shared (via ET), "I think that you have history and a past with someone and love, and just because it doesn't work out the first time, the second time, as long as there's not too much damage done, then, it can always work out again."

In June 2018, Duff announced that she was pregnant and expecting a baby girl with Koma. Their daughter, Banks Violet, was born that October. In May 2019, the songwriter proposed to Duff, and the two had an intimate wedding ceremony in their backyard at their Los Angeles home in December, per Us Weekly. In October 2020, Duff revealed that she and Koma were growing their family when she shared on Instagram that she was expecting another baby. In March 2021, the actor gave birth to a second daughter named Mae James

The married couple has since dedicated several social media posts to one another. Duff celebrated her husband on Father's Day in June 2022 with a sweet and lengthy Instagram post that read, "Thanks for also making me a girl mom @matthewkoma you are the most supportive/understanding/funny/willing/kind/father and bonus dad there is. There's no way in hell I could do this without you."