Today we’re taking a look back at that forgotten time in 2004 when a then 16 year old Hilary Duff dated TRL “bad boy” and 25 year old Joel Madden. We’ll discuss the media’s “Pop Princess VS Punk Rocker, odd couple narrative, the very Wilmer and Lindsay way they chose to announce their relationship and the very intentional shade thrown towards Nicole Richie by Hilary after the breakup.

We’ll also spend some time dissecting the intricacies of Hilary Duff’s career and how she’s been able to maintain her squeaky clean, Disney Channel image for more than a decade. PS: We also discuss her virginity because what would a conversation about an early 2000’s pop star be without a little virginity talk?

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