This is the funny and sweet story of a man that buys a hat and the range of unexpected emotions he experiences with the hat. He is excited at first, but then he struggles with worry, embarrassment and even anger. Humorous situations follow the man as he attempts to handle his insecurities. Surprisingly, he finds comfort when he adopts a cat. The hat makes another appearance and its new owner has a very different experience when he wears the hat. The story helps its readers identify the complicated feelings associated with anxiety and self-image. It explores levels of personal comfort, showing that people can have different reactions to the same experience. The book is based on a comedy bit from 'The Too Real Tour' by the hilarious and talented Marc Maron.