Free Character Writing Prompts #38: Pessimists

The glass is always half empty for these character writing prompts about pessimists. As the media becomes more negative every day and as social media makes it easier to make your complaints felt, it's tough not to create a few additional pessimists every second in this new digital age. Pessimists are able to easily downplay the positive things in their lives and to find the fault in various aspects of their day. Studies have shown that pessimists live a bit shorter than optimists, as an attitude can mean a lot to health, wealth and success. The most interesting aspect of a pessimistic character is seeing when and how they became that way, which I will play with in these next 10 character types. 

Free Character Writing Prompts #38: Pessimists

1. He was an absolute sourpuss who complained about everything that came into his scope of vision. He would drain the air from every room he walked into by noting the problems of his life, the issues of his co-workers and even his company's shortcomings. The only reason his bosses kept him around was because he was clearly able to assess the worst-case scenario in every situation. He was not allowed in any positive brainstorming sessions because his barbs acted like heat-seeking missiles to each idea. He was also frequently not involved in regular conversation as he'd find a way to make any good news you presented into something awful-sounding. What made him into such a negative person and would anything be able to reform him?

2. When you sat down to your blind date, you assumed that you'd receive the normal chit chat about life, the weather and about your respective jobs. You were surprised to hear a string of complaints worthy for a Jerry Seinfeld stand-up comedy routine. He even started one paragraph with the question, "What's the deal with these tiny portions?" You barely got a word in edgewise as he seemed to be perfectly content pointing out the flaws in the world around you. Aside from the chatter, he seemed normal enough, though he was beginning to bald, which you attributed to his constant "routine." When in his life did he turn his only conversation topic into a long-winded complaint about his existence?

3. She was one of your best friends in the world but you never told her any of your new ideas or plans for life. You remember back to telling her about your idea for a new business, when asked, "Do you seriously think you could pull that off?" and when you planned to lose 20 pounds and she said, "But you love food more than you love people." These comments would always elicit laughs throughout the room, but she meant them wholeheartedly. She didn't even know she was bringing the people around her down, she simply thought she was being honest and "There is nothing wrong with honesty." How has her attitude changed the dynamic of your friendship over time?

4. In the past, she had been something of a self-help speaker and had done some great work in improving the self-esteem of the women she spoke with. After an accident that killed her husband and left her wounded and mentally scarred, she did a complete 180. She abandoned her speaking practice and took up a job she hated because she thought she deserved it. She now believed that life was pain and that we were just living out a tough existence to keep the world going around for future generations. She mourned her husband constantly and refused to move on. What might help her to go back in the other more optimistic direction and why?

5. He was a futurist and his research had led him to believe that the world would be completely unsustainable within about three decades. He would go on talk shows and political programs preaching this point of view but it was rare for someone to take him seriously. He embarked on making a documentary that would show how imminent the destruction of the world would be. Upon its release, it was labeled "The most depressing documentary ever." He built up a small fan base of likewise pessimists who believed the end was near and that little could be done about it. He appreciated the validation. Does he believe there is anything to look forward to, why or why not?

6. He had been a man of God, until he lost both his wife and his son to cancer. He could no longer believe in a higher power that would take his loving family from him when he had been so devoted to the cause of religion. He still did his best to help those in need but from this point onward he did it all with a grain of salt. He was fine with helping his fellow man, but he no longer believed that there was anything left for us at the end of a lifetime. On most evenings, he sat in his home alone and flipped through old photographs of his family. Is there anything that could bring him out of his funk or to make him believe in God once again?

7. She loved other people and hated herself. She wanted to spend as many moments of the day with others as possible because she couldn't stand to be alone. Whenever she was alone she was stuck with her own thoughts of self-deprecation and hatred. She would look in the mirror and see nothing but faults with herself internally and externally. When she was dating, she required great deals of validation and many of her partners found her too needy after the first few months. She refused to go to therapy but if she had, she might have blamed some of the problems on her mother's constant put downs. Will she ever find someone willing to put up with her low opinion of her self and what would she have to do to live a happy life?

8. She thought herself to be one of the perkiest and cheeriest people she knew, but that's not how the rest of the world saw her. She always had a smile on her face and was quick to laugh and yet she was the queen of criticism. Her daughters always felt like they weren't doing well enough for her even though she loved them dearly. Her friends would often hesitate before calling her even though she wanted nothing more than to spend an afternoon with them. She didn't realize in the slightest how she was making them feel. What would have to happen for her to comprehend the way other people felt about the things she said?

9. He was widely known throughout the world as the film critic who hated everything, even if it was well-liked by the general population and award-winning. He wasn't able to find anything positive in the films he viewed and his sarcastic and cynical nature struck such a chord with the public that he received his own television show. His criticism extended to other walks of his life as well, including the characteristics of those around him. What is it about his life that caused him to find such fault in the film industry?

10. She was a complete knockout and when she walked around the bar, both men and women noticed. Despite the fact that almost everybody she passed thought she was beautiful, she believed that she was one of the ugliest people in the world and required constant reassurance. She didn't realize that her self-esteem was so low, she simply thought she was gross and she'd be lucky to find someone to take care of her. This caused her to get into several rough relationships involving physical and verbal abuse. What caused her to feel so low about herself and what would have to happen for her to think more highly of herself? 

Did you enjoy these character writing prompts? Buy the full book of 1,000 Character Writing Prompts on Amazon! 

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    Done with Character Writing Prompts about Pessimists? Go back to Creative Writing Prompts. 

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    Written by Bryan Cohen

    Bryan Cohen is the author of more than 30 books, many of which focus on creative writing and blasting through that pesky writer's block. His books have sold more than 20,000 copies. You can find him on and Facebook.
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