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The oldest child of Angelina Jolie and Brad Pitt seemed to go from an apple-cheeked little boy to a strapping young man overnight. Maddox has popped up on the red carpet for a few of his parents' premieres, and in 2014, his mom even revealed that the now-13-year-old had a girlfriend, saying, "He's dating, he's got a girlfriend. She's great. I won't embarrass him."