Free Character Writing Prompts #24: Pirates

Yo ho ho and a bottle of 10 character writing prompts about pirates! When creating 100 categories of characters, I was bound to have a few categories that some might find to be extraneous. I don't consider pirates to be of that ilk due to the newsworthiness of the Somali pirates a few years ago and the success of the Pirates of the Caribbean movie franchise. Pirates can be used as a dastardly villain or simply a bit of comic relief in a sea adventure. While not all pirates will be as memorable as Captain Jack Sparrow, you are bound to find some enjoyable traits within these 10 scurvy dogs. 

Free Character Writing Prompts #24: Pirates

1. He was one of the most cunning pirates of all time according to the stories and his legend had grown hugely. This was, of course, far out of proportion with the truth. While people were being truthful when they spoke of him winning large battles with inconceivable odds, it was almost always an accident. He once tripped over a lantern, which allowed him to avoid a direct hit to his body and sent a cannon ball directly into the weapons cache of another ship, blowing it to smithereens. A similar incident allowed him to defeat 10 men when a rope he was nervously gripping ended up tripping the men and sending most of them overboard. Who is this man really and how does he react when he hears his legend?

2. He was a terrible captain and nearly all of his crews had mutinied on him. Almost being the operative world. His great charm knew no bounds. Even though he frequently sent them on the wrong course and put them in bad position, he was able to flatter each man in just the right way. He eventually had his first mate secretly give all the orders as he used his talents to get secrets from the men and women of local towns to score riches for all the men on his ship. His mother had always taught him the best way to speak to person was by first listening. Will his charm be enough to keep him safe and alive during the rest of his tenure as a captain and why?

3. She was bawdy and rude and in a game of chance she'd won her very own pirate ship. As she'd been looking for a change from her brothel life, she took a few of her girls and opted to become a woman of the sea. By leveraging the services of her women, she was able to gain the respect of her mostly male crew and to stage several successful attacks on local sea merchants. She loved this new life and within a few years she became one of the most feared pirates on the seas. What was the stickiest situation she ever got into as a female pirate captain and how'd she get out of it?

4. She didn't know the rules of the water and had disdain for pirates, yet when push came to shove, she could fight her way out of any situation. After a bloody battle, she inherited the position of first mate of a crew that could help her to achieve her goal of revenge. At first, a few of her fellow shipmates thought they could take advantage of her, but after one lost an ear and another an eye, the rest of the crew left her alone. She was even willing to act as bait for other ships as a "defenseless woman" trapped in a life boat. Once she boarded, she strategically rigged the ship to explode from a cannonball in the right place and dove off once her ship came near. She knew that eventually the ship she destroyed, would include the captain who killed her father. How did she learn to be such a fierce combatant?

5. He'd always had a difficult life on land. He was cross-eyed and was certainly lacking in the dental department. On sea, however, he was able to find camaraderie and power that dry land couldn't offer him. It turned out that pirate ships were often a group of people just like him with one or multiple deformities. Nearly everyone on the ship was willing to look past these if he worked hard and kept out of trouble. He even once spotted a ship in the distance that led them to a major score. He knew that this life was dangerous but his felt his happiness was worth it. How will his time on the ship change him when he returns home to visit his family?

6. He was a frustrated teen who was tired of the iron rule of his parents. He opted to stow away aboard a pirate vessel for hope of a change. He quickly found that as an errand boy for an entire ship of pirates, it was almost as if he had ten times as many chores. Now that he was hundreds of miles away from home, he began to appreciate what he had with his parents and he lamented his decision. Since the pirates considered him a slave, it was up to him to escape upon reaching the next town. Is he successful in his attempts or will he be a pirate slave forever?

7. She no longer wanted to live a life as herself and decided to elaborately hide her gender and take to the seas as a fisherman. Only a month into her journey, she was captured by pirates and only revealed her gender to prevent certain death. The pirates had recently lost their cook and assumed that finding a woman in the middle of the ocean was a blessing. She soon became one of the boys and she loved telling lewd and crude jokes with the kind of men who would appreciate her. She even found love with one of the pirates. What will the rest of this pirate cook's life be like and why?

8. She was the daughter of the king of the pirates, at least, until she killed him to take over. She was ruthless and showed little in the way of mercy, regardless of the situation. If any fellow pirates would ever cross her, she would quickly end their lives and so many of them were scared of her, there was hardly ever a peep of an uprising. She had determined that her and the pirates must attack and defeat an armada of ships from a nearby nation and she took them to war. There was something she wanted from them. What did she want and why was she willing to kill her father to gain the power to do it?

9. He was of little use to the rest of the crew aside from unintentional comedic relief. He had one glass eye because of a fishing hook mishap and an unfortunate cannon incident had left him perched on a wooden leg. No matter how tough the seas looked and how gloomy the men were, they could always count on this accident prone man to cheer them up. At first, he looked at it all as an unfortunate burden but as the time and laughter went on, he almost relished in the cheer he brought to the other pirates. Obviously, he'd never run or blink with his left eye again, but he was able to tell jokes no matter what his deformities. What is a typical joke he would tell and what other accidents might befall him during his lifetime?

10. When her son said he wanted to become a pirate, she agreed but with one condition. The condition being that she come along to keep an eye on him. The pirates on the first ship he sailed on laughed at him in the beginning, but they soon learned that his mother was no woman to mess with. She was able to stare down and guilt any man, woman or child and she would stop at nothing to make her child safe. She even once attacked and defeated a man who made fun of her son behind closed doors. This only added to her legend. It was unsurprising then that she eventually became captain and made her son first mate. How did this woman learn to become so strong willed? 

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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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