During the 70th Primetime Emmy Awards on September 17, 2018, Weiss made headlines by proposing to long-time girlfriend Jan Svendsen during his acceptance speech for Outstanding Directing for a Variety Special for his work on that year's Academy Awards. He proposed by saying, "You wonder why I don’t like to call you my girlfriend? Because I want to call you my wife." The ring previously belonged to his mother, who had died two and a half weeks prior. The moment was widely shared on social media platforms Twitter and Instagram.