When the magazine asked about when she lost her virginity, she didn't exactly make it too hard to connect the dots.
"I had a 26-year-old boyfriend. So everyone can make their own assumptions about what I was doing," she said.
And in the time since both Hilary and Joel -- who's been married to Nicole Richie since December 2010 -- have both moved on, the former Lizzie McGuire star has managed to maintain her good girl image in Hollywood. She credits the feat to "a massive friend cleanse" she did when she was 19 years old.
"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**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."