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Before Good Charlotte singer Joel Madden married Nicole Richie, he dated Hilary Duff when he was 26 and she was 18.
But he admitted to Rolling Stone that he was interested in her long before she was legally able to vote.
Woody Allen started a relationship with Soon-Yi Previn when she was only 19 and he was 55.
Much more shockingly, at the time, Allen was living with Previn as the partner of her adopted mom, Mia Farrow.
Farrow ended things when she discovered Allen was cheating on her with her own daughter. While shooting the TV show Heroes in 2007, 30-year-old Milo Ventimiglia had a short-lived relationship with 18-year-old costar Hayden Panettiere.
The tagline for the show was to "save the cheerleader," Milo.