In the midst of showing off a shot of herself in a teensy black bikini Sunday, the "All About You" songstress also dished about her past relationship with Joel Madden, whom she started dating in July 2004 when she was only 16 and he was 25.
The two later split in November 2006, and Hilary went on to marry Mike Comrie in 2010 at 22. Joel also ended up tying the knot with Nicole Richie in 2010 after she became pregnant with their first child in 2007.
"I had a pretty serious relationship at a young age that I ended, and it wrecked me for a good year and a half," Hilary told Cosmopolitan (via E! Online). "I didn't really enjoy being single." When asked when she lost her virginity, she replied, "I had a 26-year-old boyfriend. So everyone can make their own assumptions about what I was doing."
The former Lizzie McGuire star also opened up about how she managed to stay focused during that time when some of her friends' lives went in a different direction. "At 19, I did a massive friend cleanse," she continued.
"That was really hard, to sit down with people and say, 'We can't be friends anymore,'" she continued. "They were like, 'That's f**ked up. You're a b*tch.' 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."
As for Hilary's recent bikini shot, she had no qualms about showing off the toned bod she's worked so hard for on Instagram, captioning the snap, "Hey #moms #westillgotit #loveyourbod."
If you've got it, flaunt it.