During the 70th Annual Emmy Awards on September 17, 2018, Weiss made headlines by proposing to long time girlfriend Jan Svendsen during his acceptance speech for Best Directing Of A Variety Special for his work on that year's Academy Awards. He proposed by saying, "Do you know why I don't call you my girlfriend? It's because I want to call you my wife." The ring once belonged to his deceased mother who passed 2 1/2 weeks prior. The moment was widely shared on social media platforms Twitter and Instagram.