3. Hilary Duff
We still remember cute little Hilary Duff from her Lizzie McGuire days. Another Disney starlet, she was actually really tame compared to others. So we were really surprised to learn that she had her first intimate experience when she was just a young teen. She was dating a guy 10 years older than her and she lost her virginity to him when she was just 16 years old. Wow! That was probably shortly after (or even during) her time as Lizzie McGuire. Pretty interesting considering that her character had some much bad luck in love! Actually, Hilary herself got divorced…
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