During a jaunt through the woods a few weeks before their senior year of high school, Eleanor and her friends find a mysterious wooden box. As the days pass, unexplainable things begin to happen. Any item put in the box disappears. Wishes, or something resembling wishes, start getting granted. People outside of the group begin disappearing. They begin finding messages in books and magazines; messages that suggest something far more sinister may be at work. When her friends begin to disappear, Eleanor realizes she has to stop whatever is literally tearing her friends apart. The Many Monsters of Sadness is a light hearted film that takes a turn towards darkness, suspense, and drama, about the price of getting everything you want.