Duff spoke about her three-year romance with Joel Madden back in 2005, “it was so all encompassing. It was so intense. It was my life.”
When Duff was 19 she took a break from music and acting for a couple of years and said that, "I just wasn't fulfilled in any way. I was just going on stage at night and I was like, 'I don't even know what town I'm in'...It just became so repetitive, and I was like, 'Why am I working like this? I'm supporting all these people.' It was just crazy,” she continued "taking that break, I think, really helped me step back from the whole 'Hilary Duff' thing and prioritise."
The 29-year-old singer’s next serious partner was ice hockey player, Mike Comrie, who she married in 2010 and had a son with in 2012.
Duff and Comrie split in January last year, but they are still close friends. She said that, “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.”
"All your relationships can be a success if you make it that way," Duff said to Tortorella. "Even if they don't last forever."
The singer went on to see fitness trainer Jason Walsh and but the two ended their relations after dating for a couple of months in November 2016.
Dating post-divorce hasn’t been easy for the mother-of-one, “I'll talk about anything. It's just like before I open my mouth, 'Do I want to say that?' Everyone is going to find one thing and make it sound totally different than how I was saying it."
Duff, growing up in the spotlight, led to her relationships being of media interest. She explained, “all of my relationships have been in the public eye. Whether people care or not, that's a different story."
But, she tries to ignore it and questions, "in the big grand scheme of everything, what does it really mean?"