Bizarre Writing Prompts: College Essay Edition

If you've gone through your college essays, you know that some are the boring "Tell me about yourself." Well, that's not this list.  I've looked around for some of the weirdest prompts I could find that could make some really interesting stories.  All of the questions in this first set come from The University of Chicago, which is renowned for its really creative (and weird!) questions. 

Also, if you have a prompt idea, submit it to me by email and you could be included in Volume III (with your name as credit and a link to your website of choice!).  Feel free to submit prompts for any genre.  I'll be making many more lists of prompts for romance, horror, contemporary, etc.!  

The Prompts

1. Dog and Cat. Coffee and Tea. Great Gatsby and Catcher in the Rye. Everyone knows there are two types of people in the world. What are they?

2. "A man cannot be too careful in the choice of his enemies." –Oscar Wilde.

Othello and Iago. Dorothy and the Wicked Witch. Autobots and Decepticons. History and art are full of heroes and their enemies. Tell us about the relationship between you and your arch-nemesis (either real or imagined).

3. How did you get caught? (Or not caught, as the case may be.)

4. Chicago author Nelson Algren said, “A writer does well if in his whole life he can tell the story of one street.” Chicagoans, but not just Chicagoans, have always found something instructive, and pleasing, and profound in the stories of their block, of Main Street, of Highway 61, of a farm lane, of the Celestial Highway. Tell us the story of a street, path, road—real or imagined or metaphorical.

5. The hero's great deeds are actually performed by his/her imaginary friend.  Go.  

6. University of Chicago alumna and renowned author/critic Susan Sontag said, “The only interesting answers are those that destroy the questions.” We all have heard serious questions, absurd questions, and seriously absurd questions, some of which cannot be answered without obliterating the very question. Destroy a question with your answer.

7. Have you ever walked through the aisles of a warehouse store like Costco or Sam’s Club and wondered who would buy a jar of mustard a foot and a half tall? We’ve bought it, but it didn’t stop us from wondering about other things, like absurd eating contests, impulse buys, excess, unimagined uses for mustard, storage, preservatives, notions of bigness…and dozens of other ideas both silly and serious. Write an essay somehow inspired by super-huge mustard.

8. If you could balance on a tightrope, over what landscape would you walk? (No net.)

9. How do you feel about Wednesday?

10. You are hosting a brunch of historical, literally, or other disreputable persons (think: Mad Hatter’s Tea Party). What is your menu? Who are your guests? In answering this question, imagine a scenario: We want some exposition, serious or silly, we would accept some dialogue, and we are willing to trust you to respond in such a way that your brain power, your imagination, your sense of taste, and your capacity to tell a story reveal something true about you.   [[A personal favorite, because this was the one I wrote about in my essay!]] 

Happy writing!


What are some college essay questions that would make great stories?  

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