Free Character Writing Prompts #43: 
Screw Ups

Here are some character writing prompts about some people who can't seem to get things right: the screw ups. You know you know at least one. Maybe this person is in your family or maybe the person is just an acquaintance of yours. There was one in your group of friends growing up and there is one in your apartment complex now. Sometimes, people who are otherwise kind and hardworking tend to screw up more often then others. Perhaps that person does something minor like losing a phone several times a year. Maybe it's something more drastic like demolishing a car or setting a house on fire accidentally more often than most do in a lifetime Whether it's bad luck or bad karma, there are screw ups among us that can be inserted in a comedic or tragic fashion. 

Free Character Writing Prompts #43: Screw Ups

1. You loved your brother with a passion, but he was never able to get things in his life right now matter how hard you tried to help. He'd accidentally given half his money over to a scam, left his house unlocked for thieves to steal most of his possessions without having renter's insurance and he even tripped coming up your front stairs to twist his ankle. He'd been like this his whole life and you wondered if you got all the luck while your brother suffered with none to speak of. You didn't feel guilty for this, of course, but you wondered if luck had something against your nice, but extremely ill-fated sibling. How did your brother typically react when these frequent incidents befell him?

2. He was in all of your classes in school and you always cringed instinctively when he opened his mouth. He was a semi-intelligent kid, he just used words incorrectly and generally missed the point of every classroom discussion. He might have even gotten some dates if he didn't accidentally insult the girls he was talking to when trying to compliment them. He had a group of friends who would occasionally sympathize with him, but more often they tried to get him to laugh with them when mocking his inability to say the right thing. As is often the case in college, he found his perfect fit, a girl with the same problem and you marveled at how there would be another generation of such lexically stumbling folk. What would a day be like in his household full of malapropisms and unintentional affronts?

3. She was the kind of girl who always had something extremely wrong with her outfit or makeup. Whether it was having twice as much eye shadow as necessary or accidentally revealing her bra for hours without noticing it, she just couldn't seem to ever get it together. As with most people who put themselves in sheepish situations, she was kind and dopey and loved people despite their chuckles. You thought to yourself how lucky she was to be working in the company of women who were willing to help her with her issues. You wondered if her constant wardrobe malfunctions had something to do with her former beauty queen mother making her nervous to always look her best. What are a few of her most egregious errors of appearance and what would enable her to get it together?

4. When she was sober she was overwhelmingly polite and kind. When she had even a little bit to drink she was the sloppiest, most accident prone people you'd ever met. When you met her in college, you assumed she was an athlete she came into the dorm with such frequently skinned knees and twisted ankles. It turned out that as soon as there was any liquor in her, she had the balance of a toddler but the speed of an Olympian. This was not the best combination for the integrity of her physical health. She was also quite entertaining when she drank, but the entertainment wore thin quickly after her first injury of the night. She even once fell off a second-story railing, fortunately landing in some soft bushes. What is her typical train of thought when she wakes up the morning following a party with a series of bruises, cuts and gashes?

5. In a family of secrets, he was often the one left out, due to his inability to keep a single one. This scenario wouldn't be much an issue if he wasn't such a snoop in the first place, often finding out secrets before they were told to other members of the family. His blabbering led to major scuffles between sisters and it kept most of the brother-in-laws too pissed at him to invite him to barbecues. He wasn't trying to cause problems, but he was just so excited to find out about things, that he burst with excitement and told everybody the most private of things in the most public of forums. You weren't surprised in the slightest to find out he was really into reality TV and celebrity gossip as well. Why did these "secrets" make him so excited in the first place?

6. When the phone rang, you knew that it was your brother. Who else would be calling at one in the morning? You also knew that it was an effort to get out bailed out of jail for a petty crime. Perhaps it was public urination this time or maybe destruction of public property. He'd had enough small offenses for a life sentence, but seeing as your dad had been on the force so long, he had an extremely long noose. He always called you, hoping your dad wouldn't find out first, but this time you wanted to let him stay there a couple of nights. Maybe that would teach him a thing or two. How will he endure his time in jail and will he ever learn his lesson that crime doesn't pay?

7. Sometimes you didn't know why your boss kept her around. She only had a few real responsibilities like getting the coffee and lunch orders, divvying out mail to the various employees at the office and re-directing phone calls from the main line. She couldn't get any of them right, ever. You also knew that she would never get fired because she was too beautiful and too nice. Your boss had a soft place in his heart for women worthy of the swimsuit edition of Sports Illustrated. She also didn't ever truly meet the standards of the company dress-code, but you had a tiny feeling that this was an intentional slip-up. When you finally sneaked a peak at her resume, you were astonished to find she'd attended an Ivy League university. What was the reasoning behind her constant flub ups in her work responsibilities?

8. She had a lot going for her in her professional life. She was an up and coming music producer and several of the acts she worked with were moving up in the scene. It was her day-to-day life that was an absolute mess. She frequently lost her phone, which subsequently lost her clients. She had been in several car accidents and now had to get other people to drive her around. She was frequently flustered and late to almost every part of her day and she had a difficult time planning ahead for anything due to her ever moving mind. Her busy job wasn't the cause of these constant problems as she'd been that way her entire life. Why were these issues cropping up and is there any way that she could put a stop to them?

9. All of his life he pictured himself falling deeply in love with the perfect woman and living out a fairy tale life. This image of his existence, however, didn't take into account how frequently he would say the absolute wrong thing to the people he dated. It wasn't a lack of tact or a gap in the understanding of social norms, it was simply a matter of being so nervous around the opposite sex that he could barely handle the act of conversation. His unintentional insults were so famous that they even inspired a website where girls he had dated would share their stories. This site propelled him into the public eye, which allowed him to begin pushing through the nervousness. What was it in the first place that made him so nervous around women?

10. By accidentally calling 9-1-1 during a secret high school party, she had unwittingly become known as the biggest screw-up in school. She was determined to change her image by throwing the biggest party the school had ever known. She had fantastic ideas but she rarely planned out all of the smaller details, such as how she'd get the band, food and drinks that she promised. Her and her best friend scrambled around the city the week preceding the party to find a way to provide for the several-hundred person guest list. Nothing was working for her and she hoped that her luck would turn around at the last second like it did in the movies. Does her party go off without a hitch and does she end up with the happy reputation boost ending she'd hoped for? 

Did you enjoy these character writing prompts? Check out a collection of 1,000 of them on Amazon

Done with Character Writing Prompts about Screw Ups? 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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