Hilary Duff is essentially Disney royalty and appears to have been unscathed from her years working with the major media company. She is one of the few Disney alumni that has somehow avoided major public scandals and has gone on to have a successful career in television, with How I Met Your Father being just one of those shows. Outside of her acting and music career, Duff is a dedicated mother and wife who often posts pictures of her family on social media and seems to be friendly with plenty of people in the Hollywood sphere.
Perhaps one of the most surprising friendships that she has maintained in her life is with one of her famous ex-boyfriends and their spouse, and even includes her current husband in that friendship as well, something that is not super common even outside of Hollywood.
Duff And Madden Dated For Roughly Two Years
In the early and mid-2000s, both Hilary Duff and Joel Madden were incredibly popular for different reasons. Hilary was most well known for her role on the Disney Channel original series Lizzie McGuire and for her budding music career. Joel Madden was most well known as one of the two twin members of the pop-punk band Good Charlotte.
According to Duff, the pair met through a mutual friend and developed a friendship for roughly three months before getting into a relationship with one another in 2004. Prior to that, Duff had dated the late Aaron Carter as well as Frankie Muniz.
Hilary Duff admittedly kept the relationship under wraps for as long as she could among tabloid speculation. Once things were made public, Madden appeared in her 2006 film Material Girl and allegedly influenced her Dignity album.
The pair was effectively considered rock star royalty while they were together and even though aesthetically speaking the pair were very different, fans of both appeared to idealize the couple and their relationship before they ultimately called it quits just two and a half years into their relationship.
The Pair Had A Major Age Gap 
While Hilary Duff and Joel Madden had a fairly low-key relationship, there was a huge age gap between the two that was questioned by the media. Even Duff's parents were surprised by the pair dating but eventually came to accept the relationship because they took a liking to Madden.
Hilary Duff was just sixteen years old when she started dating Joel Madden in 2004, who was already 25 years old at the time. When the relationship was first made public, the focus was less on their age gap and more on their opposite senses of style and personalities.
This made Duff feel some kind of way, admitting that people are "automatically prejudging us because Joel has tattoos or I have blonde hair. He has tattoos, so he's bad, I smile all the time so I'm perfect."
Both Hilary and Joel were very adamant that they physically took the relationship slowly, with Hilary calling Joel "the most respectful boyfriend" she has ever had.
Questions about their age gap came into play following their break-up in 2006, with questions from fans still popping up about it these days. With the passage of time, it seems that Joel may have realized what an issue their relationship was back then.
While Madden doesn't have a daughter now, he admits that if he did have a teenage daughter, he wouldn't allow them to date someone so much older.
Joel And Hilary Still See Each Other Often
Both Hilary Duff and Joel Madden have since moved on and gotten into their own respective relationships. Duff was married once before and did go through a divorce, but seems to have found love again through her current husband Matthew Koma.
Joel Madden moved on to marry reality TV star and daughter of Lionel Richie, Nicole Richie. The pair began dating in 2006 following his break-up with Hilary Duff. Joel and Nicole had two children together before eventually marrying in 2010.
And while it may shock many, it seems that Hilary, Matthew, Joel, and Nicole have cultivated a friendship together and spend time with each other often. According to Hilary "We're neighbors, and we actually hang out all the time. I was just in [their] driveway honking for [Nicole] to come drink wine with us the other day."
She also admits that Matthew and she have a "good relationship with [Nicole and Joel] whole family." While most may find their friendship bizarre, the situation appears to be incredibly healthy between both couples, with them even posting pictures of their "date nights" on social media.
Joel Madden and Hilary Duff are living proof that it is possible to have a happy and healthy friendship following a break-up not only with each other but with each other's families as well.
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