In the early 2000s, a new tween phenomenon took the world by storm.
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.
Aaron Carter
As far as first relationships go, Duff had a pretty memorable one.
Her on-again-off-again relationship with pop superstarAaron Carterwas heavily publicized and riddled with drama from start to finish.
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.
Despite the cheating scandal, Carter admitted that he was still interested in Duff a decade later.
Photos of the adorable boy-and-girl-next-door couple were published in tween magazines across the country.
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.
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.
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 toPopSugar, 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.
Although Masterson and Duff weren’t meant to be, it seems she and Alanna definitely were.
Fans even coined a combined couple name for the two of them: “Jilary”.
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.
Despite Madden’s rough-around-the-edges exterior, Duff insisted that he was a great boyfriend.
Mike Comrie
Duff began dating NHL hockey player, Mike Comrie, in 2007.
Duff was 22 and Comrie was 29 at the time.
In early 2014, Duff and Comrie separated after four years of marriage.
Around Halloween of 2016, they were pictured in costume together while out on the town.
Not long after the Halloween incident, the couple decided to go their separate ways.
Ely Sandvik
In July 2017, Duff was spotted with her new boyfriend, businessman Ely Sandvik.
Sandvik, who is rumored to be an avid surfer, is the CEO of SOLr Energy Consulting.
Photos shared byDaily Mailshowed the pair laughing and embracing each other in the waves during their two-day beach trip.
Before Duff and Sandvik had begun dating, she and Koma had a brief fling in early 2017.
Breathe Out" (perVogue).
They were first spotted together as a couple on Valentine’s Day in 2014 while vacationing in Costa Rica.
But according toPeople, 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.
They got engaged in May 2019 and were married later that year on December 22, 2019.
