Who Has Hilary Duff Dated?
9 Lucky Guys Who Have Romanced Hilary Duff Over the Years
4
Last Man Standing actor Jordan Masterson dated his Cheaper by the Dozen costar Hilary for three months in 2004, and though they didn't last, Hilary is still BFFs with Jordan's sister Alanna Masterson, who's best known for her role on The Walking Dead. The two actresses even have matching "ride or die" ghost tattoos, so it appears that Hilary's brief romance with Alanna's bro (which ended because of schedule conflicts) didn't sour their friendship. "While Jordy is a special person to me and we're still friends, the timing was just off," Hilary said of the split. "My career has to come first right now. I have my priorities straight."