The Many Famous Men Hilary Duff Has Dated

In the early 2000s, a new tween phenomenon took the world by storm. Five years before Miley Cyrus rose to stardom as the lead of her own Disney Channel show, "Lizzie McGuire" walked so "Hannah Montana" could run. The role of Lizzie was played by none other than Hilary Duff, and the show catapulted her to household-name status seemingly overnight.

Duff immediately captured the hearts of middle school-aged viewers everywhere. Teenagers related to her girl-next-door persona, but also envied her glamorous red-carpet lifestyle. Beyond her quirky personality and celebrity status, there was another major thing that young girls idolized about Duff — she was also never without a boyfriend.

At an early age, the specifics of Duff's dating life were featured in teen magazines around the globe. From music sensations to professional athletes, let's take a look at all of the high-profile relationships that Duff has had over the years.

As far as first relationships go, Duff had a pretty memorable one. Her on-again-off-again relationship with pop superstar Aaron Carter was heavily publicized and riddled with drama from start to finish. So if you cringe whenever you think back to your first middle school fling, just be grateful that the details of that train wreck weren't plastered on the cover of tabloid magazines, as was the case for young Duff.

Duff and Carter began dating in 2000 when they were both 13 years old. But trouble began to brew when Carter started getting cozy with another popular Disney starlet. In a 2005 interview with Donny Deutsch (via YouTube), Carter explained that he dated Duff for a year and a half before he became bored with the relationship and moved on to Lindsay Lohan. Carter and Lohan dated for roughly a year before parting ways, at which point he began dating Duff again. A slew of drama between Duff and Lohan ensued, but Carter candidly explained that his relationship with Duff ultimately ended after he cheated on her with her best friend.

Despite the cheating scandal, Carter admitted that he was still interested in Duff a decade later. In a 2012 interview with Fox News, Carter expressed that he was envious of her marriage to Mike Comrie, and admitted that he'll always love her. Duff didn't return the sentiment but did post a heartfelt tribute to her Instagram account to commemorate Carter after his death on November 5, 2022.

Not long after her split from Carter, Duff met Frankie Muniz on the set of "Agent Cody Banks" in 2002. Muniz already had a wildly successful career after his leading role on the popular sitcom, "Malcolm in the Middle," and he and Duff attended many red-carpet events together. Photos of the adorable boy-and-girl-next-door couple were published in tween magazines across the country.

Unfortunately, their relationship wasn't meant to last, and the young couple parted ways after only a year of dating. But they appeared to stay on good terms, with Muniz referencing the good times the pair previously had in a 2016 tweet. The nostalgic photo attached to the tweet was a still of Duff and Muniz riding a motorcycle, reminiscent of their "Agent Cody Banks" days. While Duff continued her career path as an actor, Muniz has since retired from Hollywood life and is now a husband, father, and professional race car driver.

Even though Duff only went on one date with Shia LeBeouf, apparently it was memorable enough for him to bring up in an interview with Details magazine in 2011. The year was 2002, and Duff and LeBeouf were both the stars of massively successful Disney Channel shows. According to the "Transformers" star, their date took place at a sushi restaurant. Without going into detail, LeBeouf mentioned that it was "probably the worst date" he had ever been on and that Duff probably felt the same way.

Although that may seem harsh, Duff wasn't the only superstar that LaBeouf has been on a one-and-done date with. In a 2009 interview with Playboy (via MTV), LeBeouf revealed that he had also gone on a single date with Rihanna before calling it quits with the "Umbrella" singer. Much like his previous meetup with Duff, LeBeouf and Rihanna quickly realized they lacked chemistry during their date. Although they mutually decided that romance was off the table, LeBeouf claimed that the two remained friends. It seems LeBeouf is just the type of guy who's pretty clear about what he does and doesn't want.

While filming the 2003 comedy film, "Cheaper By The Dozen," Duff met co-star Jordan Masterson. At the time, Duff was 16 and Masterson was 17. The pair entered into a relationship after the release of their movie, but the romance was short-lived. According to PopSugar, just three months after they coupled up, they amicably called it off.

But despite having lost Masterson as a boyfriend, Duff ended up gaining his sister as a best friend. Masterson's sister, Alanna, befriended Duff while the actress was dating her brother, and the two built an inseparable bond. Known for her role in "The Walking Dead", Alanna is also a successful actress and is a year younger than Duff. They are still close friends over two decades later, and Duff has posted about her and Alanna's adventures on her Instagram account many times. Although Masterson and Duff weren't meant to be, it seems she and Alanna definitely were.

Of all of Duff's past relationships, her relationship with Good Charlotte vocalist, Joel Madden, may be the most infamous. Fans even coined a combined couple name for the two of them: "Jilary". At the time, people were surprised to learn that Duff and Madden had coupled up since they appeared to come from completely different worlds. And even more shocking was their considerable age difference. The lovebirds were eight years apart and began dating when Madden was 25 and Duff was only 16. While a grown man dating a minor certainly wouldn't go over well today, apparently it wasn't so egregious back in 2004.

Despite Madden's rough-around-the-edges exterior, Duff insisted that he was a great boyfriend. In a 2006 interview with the now-defunct Teen People magazine (via MTV), Duff and Madden explained that the rock star had been sober for two years at that point, and even hung out with Duff's mom from time to time. In 2016, Duff spoke about the relationship with her "Younger" co-star, Nico Tortorella, on "The Love Bomb" podcast, saying it was the first time she was ever truly in love.

The couple split after about two and a half years of dating, but they have stayed friends — which is fortunate since they're actually neighbors today. During an interview with Andy Cohen in 2023, Duff explained that Madden and his wife, Nicole Richie, live next door to her and Matthew Koma and that they all hang out often.

Duff began dating NHL hockey player, Mike Comrie, in 2007. They got engaged in Hawaii while on vacation with Duff's family and got married in Santa Barbara, California on August 14, 2010. Duff was 22 and Comrie was 29 at the time.

Two years into their marriage, Duff and Comrie welcomed a son, Luca Cruz Comrie, on March 20, 2012. During an appearance on the "Motherly" podcast in 2019, Duff explained how that time in her life was isolating, and that she lost touch with her identity during the early years of motherhood. Nonetheless, she expressed that she had always known she wanted children, and considered it the most important job in the world.

In early 2014, Duff and Comrie separated after four years of marriage. Per a source who spoke with People, the relationship didn't end as the result of any major drama, but rather because the two had simply drifted apart. The pair remained friends as they continued to co-parent their son but filed for divorce in February 2015 which was finalized a year later in February 2016. Though it was a difficult time for the "How I Met Your Father" star, Duff has said that she still has a great friendship with her ex-husband today.

The same year Duff split from Comrie, she began dating fitness trainer, Jason Walsh. They were first spotted together at the Los Angeles restaurant Petite Trois (via People) on March 28, 2016, one month after her divorce was finalized. Their relationship appeared to be fairly casual, until Duff posted a photo of her kissing Jason to her Instagram account in October 2016, officially confirming their relationship.

Their romance didn't last long, but in the short amount of time they were together the couple still managed to stir up some controversy. Around Halloween of 2016, they were pictured in costume together while out on the town. Duff dressed as a pilgrim, while Walsh dressed as a Native American chief, complete with a feathered headdress and red face paint. Many took offense to their choice of costume, especially given the ongoing protests regarding the Dakota Access Pipeline at the time. After the backlash Duff took to Twitter to apologize for the costume, saying that it wasn't "properly thought through."

Not long after the Halloween incident, the couple decided to go their separate ways. People reported on December 1, 2016, that the pair had split, mainly due to the fact that their careers and family lives were pulling them in opposite directions. While Duff's son and work were in Los Angeles, Walsh reportedly wanted to move to New York, effectively leaving the couple at an impasse.

In July 2017, Duff was spotted with her new boyfriend, businessman Ely Sandvik. The couple was pictured together while they spent a weekend in Malibu together, soaking up the sand and surf. Sandvik, who is rumored to be an avid surfer, is the CEO of SOLr Energy Consulting. Photos shared by Daily Mail showed the pair laughing and embracing each other in the waves during their two-day beach trip.

While there was no official announcement that the couple had split, Duff's fans noticed in September 2017 that she and Sandvik were no longer following each other on Instagram. This led people to believe that the couple had moved on, which was confirmed the following month when Duff posted photos from her 30th birthday party featuring Matthew Koma on Instagram. Before Duff and Sandvik had begun dating, she and Koma had a brief fling in early 2017. The Instagram photos of Duff and Koma together in October confirmed that they had rekindled their relationship, which led to the marriage between the two that we all know and adore today.

Duff met musician and producer Matthew Koma in 2013 while working together on her album, "Breathe In. Breathe Out" (per Vogue). Their relationship was platonic at the time since Duff was still married to Comrie until 2016, but while collaborating on music together, Duff and Koma formed a strong friendship that eventually developed into a romantic relationship.

They were first spotted together as a couple on Valentine's Day in 2014 while vacationing in Costa Rica. Koma posted a snapshot of two polaroids to his Instagram account, one of them picturing him kissing Duff's forehead as she rested on his chest. But according to People, the couple split up less than a month later in March 2017. Duff went on to have a short-lived relationship with Sandvik that summer.

But by October 2017, Koma and Duff's relationship was back on. In addition to celebrating her 30th birthday together, Duff officially confirmed her relationship with Koma in December 2017 in an interview on "The Talk" (via Us Weekly.) According to Duff, this was actually their third time dating, although it's unclear when the third fling took place. From there, their relationship only grew stronger, and the couple welcomed their first baby girl together on October 25, 2018. They got engaged in May 2019 and were married later that year on December 22, 2019. The couple welcomed a second baby girl on March 24, 2021, via home birth, which was infamously documented on Duff's Instagram.