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This moment of Chad and Hilary doing what we all do best. Hilary Duff and Chad Michael Murray in their prime. Hilary Duff Had A Huge Crush On This Hunky Co-star. Carolyn L. Hilary Duff Crush Chad Michael Murray Pop CultureBritney Spears' Boyfriend Says He Has “Zero Respect” For Her DadNatalie MorinFeb 9, , PM. A Dramatic Timeline of Hilary Duff and Lindsay Lohan's Iconic s Feud After dating Hilary for nearly two years, the singer started a relationship Friday costar Chad Michael Murray — who was playing Hilary's onscreen. Chad Michael Murray discusses his 'A Cinderella Story' character and why he couldn't see Hilary Duff with a tiny mask on.