Hilary Duff rose to fame as Lizzie McGuire. Behind the scenes, she was struggling to 'fit in'.

For millennials, Hilary Duff was one of the most prominent figures of our childhoods.

We watched her on Disney and rushed to theatres for The Lizzie McGuire Movie, we sang along to her albums and we were extremely invested in the Aaron Carter/Lindsay Lohan/Hilary Duff love triangle. Those were the days.

Duff was best known in the early 2000s as the squeaky-clean Disney star but it would be naïve to suggest the 33-year-old’s life in the spotlight has always been smooth sailing.

In 2001, Duff began dating Aaron Carter, who then dumped her for Lindsay Lohan before breaking up with Lohan to get back with Duff. It became a thing, with tweens around the world far too emotionally invested in the love triangle.

Duff and Carter continued an on-again-off-again relationship for three years before calling it quits for good because he cheated on her with her best friend. That was 15 years ago, but still, we haven't forgiven him.

In June 2004, Duff moved on with Good Charlotte singer Joel Madden, causing controversy at the time as she was 16 and he was 25. They dated for two years before breaking up in 2006.

Reflecting on this time in her life, Duff told Health she struggled with body image throughout her teen years and felt the pressure to 'fit in' with a body-image obsessed industry.

"When I was 17, I was totally obsessed with everything I put in my mouth. I was way too skinny. Not cute," she said.

"And my body wasn't that healthy – my hands would cramp up a lot because I wasn't getting the nutrition I needed.

"That constant pressure of wanting something different than I had? I regret that. I feel like there was way too much time spent thinking about that."

But unlike other Disney stars, Duff didn't have a 'wild' phase. If she had struggles, she kept them private.

"At 19, I did a massive friend cleanse," she told Cosmopolitan.

"That was really hard, to sit down with people and say 'We can't be friends anymore.' They were like 'That's f**ked up; you're a b**ch.'

"But having a good reputation was important to me. That's not to say I didn't screw up and do little naughties here and there."

After years of being tied to Disney and her role as Lizzie McGuire, Duff began transitioning from 'teen' to 'adult' actress in the mid-2000s.

Her most obvious attempt to shred her Disney image came in 2007, when Duff posed on the cover of Maxim, accompanied by the words "from the queen of teen to breakout sex symbol".

This was at about the same time she started dating hockey player, Mike Comrie. The couple announced their engagement and married in 2010, announcing her pregnancy not long after in 2011.

Duff gave birth to a son, Luca, in March 2012.

Following Luca's birth, Duff told Health she learned to shake off the hang-ups she'd faced as a teenager and embrace her body.

"Oh my God, everyone was so hard on me because it took me a year and a half to get my body back!

"This is the body that I have. I have a very athletic build, and I am so proud of what my body has done for me. I had the best, healthiest, strongest pregnancy. And I feel good about myself."

In 2014, Duff and Comrie separated and in February 2015 Duff filed for divorce, citing irreconcilable differences, although she maintained they were still close and dedicated to bringing up Luca together.

"I think that I was in a very successful marriage for a long time," she told her Younger co-star Nico Tortorella on his podcast The Love Bomb.

"We got together based on love, and we separated in a very loving way. I can't imagine going through that process with anyone but him, and he continues to be my very good friend.

"That's honestly speaking from my heart. So, I think we handled it very consciously and with a lot of love."

Just months after their divorce, Duff was offered a role on Younger – and she almost didn't take it because it meant moving herself and Luca to New York City.

She reconsidered after a call from the show's creator - Sex and the City's Darren Star - and after falling in love with the character of Kelsey.

"[Her character Kelsey] is grown-up but makes a s**t ton of mistakes, which I loved. I didn't get to make many mistakes publicly in my life. I was always concerned with what people would think."

In January 2017, Duff started a relationship with musician Matthew Koma, who she had met while working on her 2015 album Breathe In. Breathe Out.

In December of that year, Duff told The Talk things were "going so great" after breaking up and getting back together earlier in the year over conflicting schedules.

"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," she said.

In June 2018, Duff and Koma confirmed Duff was pregnant with their first child together and on October 25, 2018, she gave birth to daughter Banks Violet Bair.

These days, Duff is feeling content, putting the body image issues she faced due to growing up in the public eye behind her, despite a "hard as hell" second pregnancy.

"Image is something we're all very aware of because it's constantly being talked about, which is a little bit disappointing, and then also helps you be very in tune with yourself - your behaviour, your body, and your happiness," she told BYRDIE.

"I really feel like I have a healthy relationship with myself, where I know when I'm being ‘bad' or I know when I'm being really ‘good' health-wise, and both are necessary for me as part of my lifestyle and happiness, to have balance.

"I really try to treat my body well. And my mind. And try to have a healthy outlook on [the public scrutiny]. I'm the only one that can control my relationship with myself, and I want to constantly be in control of it, you know? Whatever ‘it' is."

In 2016, Duff said getting married again was a big "maybe", but her relationship with Matthew has swayed her. On May 9, 2019, Duff confirmed in an Instagram post that she and Koma were engaged.

 

View this post on Instagram

 

He asked me to be his wife♥️

A post shared by  Hilary Duff (@hilaryduff) on May 9, 2019 at 7:20am PDT

“He asked me to be his wife,” Duff captioned a picture of the couple, showing her holding up her hand to show her new diamond ring.

In August that year, it was announced that Duff would reprise her role in a Lizzie McGuire reboot. 

"We are standing in what will soon be the McGuire living room. What’s up fam. We doin' this," she wrote on Instagram, alongside a photo of her on-screen family.

 

View this post on Instagram

 

A post shared by Hilary Duff (@hilaryduff) on Oct 24, 2019 at 2:18pm PDT

Unfortunately in December 2020, it was announced that the series was not moving forward.

Sharing the news on Instagram, Duff explained that "despite everyone’s best efforts, it isn’t going to happen". 

"I’ve been so honoured to have the character of Lizzie in my life. She has made such a lasting impact on many, including myself," she began the post. 

"To see the fans’ loyalty and love for her, to this day, means so much to me. I know the efforts and conversations have been everywhere trying to make a reboot work but, sadly and despite everyone’s best efforts, it isn’t going to happen."

View this post on Instagram

A post shared by Hilary Duff (@hilaryduff)

"I’m very sad, but I promise everyone tried their best and the stars just didn’t align. Hey now, this is what 2020’s made of," she concluded the post. 

In March 2021, the actor announced that she's welcomed her second child with Koma, a baby girl named Mae James Bair. 

"We LOVE you beauty 3-24-21," she wrote on Instagram. 

View this post on Instagram

A post shared by Hilary Duff (@hilaryduff)

The news comes after Duff shared an Instagram photo of her daughter Banks, who she referred to as a "big sister". 

"I’m a big sister....... marinating on how I feel about that!" she wrote on Instagram.

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A post shared by Hilary Duff (@hilaryduff)

This article was originally published on December 2, 2019 and has been updated.

Feature Image: Getty + Mamamia.