What's the saddest thing that occurred in your life?
What's the saddest thing you ever encountered?
What is the saddest thing you never shared? What is the saddest thing you have ever written? What is the saddest thing you have ever read in a book? What is the one thing you did that makes you sad? What is the saddest book you've ever read? What makes you feel sad the most? What is the saddest movie you have watched? What is the one thing that makes you sad about yourself? What is the saddest book ever? What's the saddest book you've read or heard of? What was the worst heartbreak you ever suffered? What made you sad today? What are some of the saddest movies ever made? What was the worst heartbreak you've ever had? What is the shortest sad poem you have ever written? What makes you sad today? What makes you feel so sad? What was the most horrifying thing that has ever happened to you? What is the silliest thing you've ever fought about? What are some of the saddest movies? What is the saddest funny movie? What is the sickest and most messed up thing about you? What did you see today that made you sad? What are some real life sad stories? What do you have to do when you are sad? What is the saddest thing about my India? What is the saddest moment in A Song of Ice and Fire? What is the most horrible thing you have ever done? What's the most frustrating thing in your life? What is a short sad story?