Hilary Duff is released her new single, "Chasing the Sun," this week and it got us thinking of how much we loved her back in the day. Before she was a sweet mother to her son, Luca, she was a — sometimes literally — animated teenager on Lizzie McGuire with the coolest friends and a sassy personality. Hilary was one of the early-'00s It girls, not only starring in her own TV show and movie but also romancing Chad Michael Murray in A Cinderella Story and both Aaron Carter and Joel Madden in real life. We're coming clean about our total girl crush. Source: Getty / Gregg DeGuire
And we all know she should have ended up with Gordo too.
He may have been lesser known in comparison to Lil' Bow Wow, but still. This was notably for "Tell Me a Story" off her holiday album, Santa Claus Lane.
Both her and her actress sister, Haylie, wore belly-baring tops and chopsticks in their hair at the Kids' Choice Awards in 2002.
She and veejay Damien Fahey were always adorable together.
They reportedly dated from 2001 to 2003, until Lindsay Lohan got between them. Bringing us to . . .
Though it's hard to see two of your favorites fight, the idea that Hilary and Lindsay were feuding over who got to be with Aaron Carter is kind of amazing. Source: Getty / S Granitz, Jason Squires
He was the bad boy who was almost 10 years older than her, but they were adorable together for two years, from 2004 to 2006.
Don't lie: you totally told your ex he was "so yesterday."
Cadet Kelly is just so good, and she also romanced pre-X-Men Shawn Ashmore in it.
This was definitely our ringtone for many years.
Why not take a crazy chance? PS: the best part is when she raps.
This was at the MTV Movie Awards right before he made out with Rachel McAdams on stage.
This was actually in 2009, but we're still going to count it.