What Happened When I Posted 731 Writing Prompts Online (part 1)

(Also, here are 183 of those prompts!)

On January 1, 2020, I had no idea what a strange year was in store for us. But things were already plenty rocky and weird that winter, and I decided to distract myself by posting one original writing prompt a day on Twitter, with the hashtag #366prompts. (It was a leap year!)

I’m so glad I did. Especially once lockdown started, I had a community of writers participating either by posting things in response, or just writing on their own. Several published stories came out of it (cue my proud-mama weeping) and it was also just a lot of fun.

Image by the Canadian artist Barbara Moustafa

I did the same thing again in 2022, with 365 more. I’m going to post them all here, in four batches—so they’re finally all in one place, and so you can have a whole lot of weird writing prompts, if you want them.

I’m allergic to vague prompts (“Write about a time you were sad!” “What frightens you?”) and much more interested in extremely specific ones that get us writing about things we haven’t already said a hundred times. Also, my brain could generate fifteen of these an hour (thanks, ADHD!) and it was nice to have somewhere to put some of them.

One unsettling thing about assembling all of these* is that I start to see unexpected repetitions, things I didn’t know I was obsessed with: genies, bad teachers and people you went to school with, science fairs, politicians, and for some reason (you’ll see in subsequent posts) specifically Michael Dukakis. I think it’s because is name is fun to say.

(*shoutout here to my former assistant, Keaton, who salvaged these all from Twitter and put them in a literal spreadsheet)

Anyway, here’s the first quarter of them, with some responses that made me happy interspersed.

---

1. The creepiest teacher from your high school: You wind up on a plane next to him. He doesn’t recognize you. He’s allergic to the peanuts.

2. Put a fish tank in one of your preexisting story drafts. The fish have some kind of fungus.

3. There’s one typewriter repairman left in the state of Maryland.

4. Go to a museum near you (or go virtually to a museum far away). Walk around a room, and stop at the most disturbing thing you see. Make yourself stare at it for ten full minutes. Then write.

5. A garden party. A frog. A cracked pitcher of lemonade. Agnes is drunk. The UPS guy joins the party. His name is Jarvis. He’s up to something.

6. Take the boring adult conversation scene you already wrote, and put a kids’ sleepover in the basement, one they have to deal with every few minutes. If your characters don’t have kids, they’re babysitting.

7. Your uncle’s trick for slicing tomatoes.

8. Who is the richest person you know in real life? You wind up alone in this person’s bathroom, and no one will miss you for ten minutes. What do you do?

9. The Museum of Morality

10. Pick a character you’re already writing about. Give your character the stomach flu. No, it doesn’t mean they’re pregnant. It’s just the goddamn stomach flu.

11. Put a Magic 8 Ball in your story.

12. You live in the city, in a small duplex with a tiny backyard of dirt. A wealthy neighbor calls and says he wants to hire a gardener to make your yard a flower garden, because he can see it from his window and wants to look at something nice.

13. This is the hotel room where a famous comedian from your childhood overdosed and died.

14. Write the opening line of a novel. (You don’t have to write the novel.) The opening line has to contain an avocado and a fire hose and the letter Q.

    

    This one literally made me cry.

15. Make a list of every Sarah (or Sara or Sari or Zara) you’ve known in person. Describe them all in detail.

16. You’re in the international first class lounge at the airport by mistake.

17. How hard could it be to superglue a butter dish together again?

18. Meghan is your bartender. It’s Meghan’s last night.

19. The sociology professor hasn’t shown up to class for a full week now.

20. The chickens of Moscow

21. People who work in the drive-thru window at Starbucks get an inordinate number of bee stings.

22. Find your high school yearbook and open it at random. Slam a finger down, and write about the kid you’re pointing to.

23. The mother of the bride is drunk.

24. Take a central location in the thing you’re writing, and light it on fire.

25. What is your relationship to umbrellas?

26. Setting: Tae Kwon Do belt testing for small children.

27. There’s a language in which the words for “yes” and “no” are easily mistaken for each other, especially when whispered.

28. Dog church. It’s a church where you bring your dogs!

29. You thought you could just drop your kid off at this birthday party and leave, but apparently all the parents are staying and drinking wine while their kids watch the bubble guy perform.

30. The vending machine in the basement of the rec center.

31. There are thirty tiny polar bears living in the refrigerator.

32. Your niece wants to play horses with you.

33. The story starts with a lost retainer in a college cafeteria. It ends with someone crying about curtains.

34. Spend a paragraph describing a particularly ugly potato.

35. Find a boring scene you’ve written, and give a character a yoyo.

36. You get matched with someone on a dating app, and meet up. S/he does not remember that s/he was in your 8th grade class and incredibly mean to you, but you do.

37. Charmer’s Almanac

38. Put your character in a bad situation, and then make it worse. And then make it worse again. And then make it worse again. And then: Gladys shows up.

39. The doctor gives you a prescription, and when you go to pick it up it’s a genii in a bottle. The pharmacist asks if you have any questions.

40. Alex is visiting you from Florida, and has never seen snow before.

41. Open Shakespeare, or a religious text, or something Greek or Roman or mythological, at random. Copy down the first line or fragment that catches your eye. That’s your title.

42. No matter your gender, catalogue some of the ways in which you are sexist.

43. The story starts with someone making their own yogurt.

44. The worst shoes you ever owned.

45. Two people try very hard to have an affair, but find themselves physically incapable of consummating it.

46. You’ve gotten someone else’s paycheck in the mail.

47. Your character’s friend is involved in an essential oils pyramid scheme.

48. Take the story you’ve attempted, the one that isn’t working, and make it a Christmas story. Your characters don’t have to celebrate Christmas; it just has to be December 25th.

49. Your own face starts appearing on Missing posters in your neighborhood.

50. Whatever thing you’re working on, put a Monopoly game in there within the next three paragraphs.

51. It’s Jorge’s last day at the Butterball Turkey hotline, and he has nothing to lose.

52. Tornadoes can fully pluck chickens but leave them alive.
    [This is true.]

53. Every person you meet today within the context of their job (barista, Lyft driver, dental receptionist), ask them what’s the strangest thing that’s happened to them at work. Pick one to write about.

54. The story starts with someone window-shopping for cowboy boots, and ends with the funeral of a high school history teacher.

55. Write a story from the viewpoint of Vanna White.

56. You take a mail-in DNA test, and a week later the FBI calls.

57. What item of clothing have you owned the longest?

58. When you get to heaven, it turns out there’s a lot of exercise equipment involved.

59. Take a boring character in a thing you’re already writing, and reveal that they were a child oboe prodigy.

60. Setting: the 8th birthday party of a guy born on Leap Day 32 years ago. It’s 8-year-old themed.

61. The chiropractor has been murdered in his office. You were his last appointment of the day.

62. Strep foot. It’s a thing.

63. Click “random” on Wikipedia, click the most interesting hyperlink from that page, then the most interesting hyperlink from THAT page. Go eight levels in; the page you landed on is your subject.

64. Feuding ice cream parlors.

65. Describe eating a scented candle.

66. The grown siblings still play the arcane Frisbee game they invented as kids, every time they’re all together.

67. Self defense class for college freshmen. It’s taught by Walter the security guard.

68. It turns out that all this time, owls were a hoax.
    [I believe that at the time I wrote this one, the whole “Birds Aren’t Real” satirical conspiracy theory wasn’t really a big thing]

69. The mysterious cookies in the teachers’ lounge.

70. A celebrity starts a salad dressing brand. Not that celebrity. Another one.

71. What is wrong with your back?

72. Your elementary school bathroom. Describe it in detail.

73. The church youth group retreat is in the same hotel as a witch conference.

74. What color is the letter E?

75. That is not your granola.

76. St. Patrick’s less famous brother, Cormac the Mild

77. What ever happened to your prom date? (bonus prompt if you didn't go to prom: what'd you do instead?)

78. A wallet left on the sidewalk as a psychological experiment.

79. The story starts with three children finding a high school history textbook in the woods.

80. Saturdays are for inventory.

81. Write the first sentence of a story. It must contain a broken umbrella, a British monarch, and the letter X.

82. What is your relationship to stretch marks?

83. The jar of kimchi in the back of the fridge. You don’t know how old it is.

84. Go back to the last short piece you finished writing (but that you’re not happy with yet) and force yourself to add one more paragraph or stanza to the end. If things had to keep going, where would they go?

85. You drive past your old house, and the new owner is taking out the lilac bushes.

86. Set a story at a mountain resort that hasn’t changed in a hundred years.

87. Your character puts on last spring’s light coat for the first time in eleven months, and finds a love note someone slipped in there last year.

88. Take a scene you’ve already written and put it in a hotel room. The couple in the room next door is having way too much fun.

89. What did the Spanish teacher get fired for?

90. Go back to a recent draft and add five different smells. At least one of them must be wretched.

91. That nice young couple from the cruise.

92. Whatever you’re writing, find a way to get your character to a religious service. Especially if it’s one they’re uncomfortable with.

93. The thing you know a weird amount about because you did a report on it in grade school.

94. This picture:

95. What were the wild spaces of your youth? (Not the lovely park, necessarily, but the weird mint patch behind your grandmother's house, the sewage ditch where you threw rocks, the dirt pile...)

96. What is the first political election you remember in detail? What are the physical details of your memories? (The TV you watched on, what was for dinner, etc.)

97. There's a turtle on the pitcher's mound. It's definitely Carson's fault.

98. Click through Facebook (friends of friends) until you find a first-and-last name combo that sounds like a great character. Post the name here, if you want; we probably don't know them.

99. You know those letters they sometimes make you write your future self from camp, and then they mail them ten or twenty years later? It's time for your main character to get one of those.

100. What your story really needs right now is a Carmelite nun.

101. Give your main character an obsession with a dead movie star. Ideally one you yourself are obsessed with.

102. Write about the worst (in a benign way) sex that your character ever had.

103. A character in your work-in-progress looks disturbingly (to everyone else) like Henry VIII.

104. What do you know how to cook better than most people? Put it in your story. It's actually kind of wildly fun to watch characters cook, plus I'm hungry.

105. April, 1995.

106. Bart Shingledecker, Jr.

107. Write the first line of a story about the mafia (or about a group of friends playing mafia). It must contain a pair of sewing scissors, a yellow purse, and the letter Z.

108. The wax museum of serial killers.

109. Your worst birthday

110. Give your character a houseplant. One with issues. Make it important. Make it weird.

111. The most famous person who went to your high school comes back for a visit.

112. Write story or a poem that's an angry letter to the worst teacher you ever had.

113. Margot was not invited to this party and yet here she is, and she brought her very small dog.

114. Your friend and his new girlfriend don't realize their Venmo transactions are set to public, and you're learning way too much about their sex life.

115. Write about the fact that Sirhan Sirhan is still alive, watching the altered timeline he created play out.

116. Your top five memories of shopping malls.

117. Whatever you're writing, put a skunk in there. I don't care if it's a novel set in space or a sonnet about you grandmother. Put a skunk in, I dare you.

118. Build a shrine to your work-in-progress. Photos, objects, related books, candles, stuff you find on walks. Add some things you like but that have nothing to do with with story yet. Eventually, they will.

119. Write a paragraph about your childhood dentist. Not the office, but your actual dentist.

120. The LEGO store at the mall, three days before Christmas.

121. There's a chipmunk in the bathroom.

122. Write a paragraph about your first part in a school play or talent show. (I was a merchant, and I was supposed to be hawking pastries, so the moms on the prop crew gave me a tray of unfrozen Eggos.)

123. The story starts with a character giving a dog a bath, includes a discussion of the Siege of Antwerp, and ends with an election party gone wrong.

124. Thirteen Ways of Looking at Yoko Ono

125. Go into a scene in you work-in-progress that's falling flat. Find an excuse to get one (only one) character drunk. What are they going to blurt out? And what's the fallout?

126. Write a paragraph about the feeling of getting pool water up your nose.

127. Write a story, poem, or essay called "Al Capone Gets 11 Years"

128. A single mother in Detroit finds a genii in a jar of peanut butter.

129. You are drinking your morning coffee and watching the news cover an outdoor press conference live. As you're watching, the president dies. How does he die, and what do you do next?

130. There aren't enough short stories/essays/poems that center around a single karaoke night. Please write one.

131. Write a story, poem, or essay called “Controlled Burn.”

132. Write a horror story set at a highway rest area. OR Write an ode to a highway rest area.

133. The story starts with a chance celebrity encounter, includes sidewalk chalk, and ends with a pie-eating contest.

134. The most popular kid in 5th grade.

135. Write the first line of a story or novel. It must contain a frog, the letters J and K, the pledge of allegiance, and a pasta-based simile.

136. Write a thank-you note to someone who was mean to you in high school.

137. The Christmas tree is still up.

138. Find the eeriest stock photo you can. Either write a poem about it, or work it into a piece of prose in progress.

139. “Mr. Ungrateful”

140. The story starts with a neighbor’s dog showing up, includes a strawberry pie, and ends at the middle school basketball championship.

141. Write an obituary for a lamp.

142. The story starts with a skunked bottle of wine, includes a battery crisis, and ends with Malcolm setting something on fire.

143. "Swallowed a Fly"

144. "Left-Hand Man"

145. "The Lookout Girl"

146. "Your Cousin and Your Cousin's Cousin"

147. "Alice the Maid and Sam the Butcher"

148. Write at least 100 words about the first news story that filled you with rage.

149. Make a list of twenty-five things that you're angry about.

150. The story starts in a doctor's office waiting room, where your character makes a life-changing discovery in a year-old issue of People Magazine. It includes strawberry ice cream, and it ends on a delayed flight home from Moscow.

151. The story starts with an overdue library book, includes someone mansplaining quail eggs, and ends with an international incident. It's called "Envelope, Envelope."

152. Put a 12-year-old neighbor in your story.

153. Put the smell of burned popcorn in your story.

154. Put a FitBit in your story.

     

155. Put the Greek mythological torturer Procrustes in your story.

156. Write a noir detective mystery, but the client is Winnie the Pooh. Like, the detective is sitting there in his office, and in walks Winnie the Pooh with a gruesome murder for him to solve.

157. Invent an absolutely obnoxious kids' television show and put it in the background of your story or novel. Make up song lyrics for it, too.

158. Find the absolute oldest thing in your bathroom. It's probably in your medicine cabinet, but it might be a very old lipstick. Hold it in your hands for two minutes, and then start to write.

159. The story starts with a blackmail note, includes a visit to Chicago’s Museum of Surgical Science, and ends with a fight about road kill.

160. Give your character a memory about tennis. The memory involves a raccoon, a lollipop, and a girl whose nickname was Squawk.

161. Whatever you’re working on, put a stale rice cake into it.

162. The utopian grocery store.

163. Go somewhere you've never been via Google Street View. Then go on Wikipedia and find out the history of the place as precisely as you can. Your character's date or college roommate or mother is from this place now.

164. The story starts with a trick deck of cards, includes a story about a tiger tamer, and ends with Gretchen taking a vow of chastity.

165. Pretend that in your life you have known two very different people both named Leslie Sutter. Write about both of them.

166. Stick an incredibly irritating housefly in a scene that needs one. The fly is not symbolic.

167. The absolute weirdest kid you went to high school with.

168. Set an entire story in a shoe store. Include a deck of flashcards and some origami. It starts with the word "credit."

169. Make yourself a really, really, really good piece of toast. Slather it with butter and salt or whatever you love. Eat it very slowly. Write about how it tastes.

170. Give a character suspenders to wear.

171. Give your main character a signature dish that they're amazing at, even if they don't know how to cook anything else. Then go read some very specific tips/watch videos about how to make it. Then either write about it or quit writing and become a chef.

172. Write a full paragraph about dandelions.

173. Write the first line of a story or poem. The line must include the word "flagrant," a glass of vodka, a porcupine, and a sense of ennui.

174. Start a story in a Starbucks bathroom. I mean, start your scene there, do not actually go to the Starbucks bathroom to write.

175. Go on Zillow and pick out a house for your character. Take screenshots.

176. Set an entire story in a laundry room. OR Write an essay about a laundry room. OR Write a poem about a laundry room. OR Do your actual laundry.

177. Your butter keeps vanishing.

178. You're meeting Robocop's girlfriend for the first time, and you're nervous.

179. The story starts with someone discovering an antler. It includes SAT prep and a broken toilet bowl, and it ends when the Duran Duran poster finally comes down.

180. Write about a camera shop called Hocus Focus.

181. Write a poem or essay about what you're going to wear to vote this November.

182. Set an entire story in an IKEA. You know you miss it.

183. Your main character's computer breaks down completely mid-story. Sad Mac and everything. All documents lost. How does this destabilize the story?

     Stay tuned for parts 2, 3, and 4… And if you’re a paid subscriber, please feel free to share any prompt responses in the comments!