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The two first met on the set of Hilary's hit show, Lizzie McGuire, in 2001 and dated for almost two years before Aaron started dating Lindsay Lohan — at the same time. The pair officially called it quits in 2003, but Lindsay and Hilary's feud continued well beyond their breakup. In 2014, Aaron resurfaced the tween romance when he reposted a picture of Hilary and tweeted, "I'll spend the rest of my life trying to better myself to get back to her. I don't care what ANY of you think."