Hilary Duff was left 'wrecked' by the end of her relationship with Joel Madden.
The Lizzie McGuire actress dated the Good Charlotte frontman when she was 16 and he was 25. They broke up in 2006 and while Joel has gone on to marry Nicole Richie, Hilary recently filed for divorce from husband Mike Comrie, who she has son Luca with. But despite so much water under the bridge, the 27-year-old can still recall how she felt at that time.
'I had a pretty serious relationship at a young age that I ended, and it wrecked me for a good year and a half," she told the American edition of Cosmopolitan. "I didn't really enjoy being single."
The couple began dating in 2004 and were photographed on the red carpet many times together. The age gap certainly raised a few eyebrows, and when the subject moved onto losing her virginity, Hilary didn't try very hard to conceal who was her first.
'I had a 26-year-old boyfriend. So everyone can make their own assumptions about what I was doing," she told the publication.
While she had a much older partner, Hilary somehow managed to hang on to her good girl image. She credits that with having a solid group of friends around her, having cut ties with other pals who didn't fit her lifestyle when she was 19.
'That was really hard, to sit down with people and say, 'We can't be friends anymore,'" she revealed. "They were like, 'That's f**ked up. You're a b***h.' 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."
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