17 of the Most Fun College Essay Prompts of the Past Year

You’re sitting at an interview for your dream job, rattling off the various awards you’ve won and strengths you would bring to their company. Suddenly, the interviewer pauses and asks, “What’s the craziest thing you’ve ever seen on TV?” In this serious moment, you’re given a chance to let your hair down and show a little bit more of the “real you” – which is exactly what these creative, sometimes even outlandish, college essay prompts do. These 17 essay prompts gave applicants a chance to get inspired and think outside of the box, and that’s why they’re some of our favorites from the past year.

It can be tricky to figure out how much fun to have with these prompts – after all, you’re still trying to impress the college admissions counselor! Making yourself stand out is crucial… but it’s got to be for all the right reasons!  At the The Enrichery’s College Admissions Workshop, our coaches will help applicants write their main essay and strike the perfect balance with their quirkier supplemental essays. Reserve your spot ASAP!

University of Chicago

Who does Sally sell her seashells to? How much wood can a woodchuck really chuck if a woodchuck could chuck wood? Pick a favorite tongue twister (either originally in English or translated from another language) and consider a resolution to its conundrum using the method of your choice. Math, philosophy, linguistics… it’s all up to you (or your woodchuck).

Dartmouth College

In The Painted Drum, author Louise Erdrich ‘76 wrote, “… what is beautiful that I make? What is elegant? What feeds the world?” Tell us about something beautiful you have made or hope to make.

Yale University

You are teaching a Yale course. What is it called?

Tufts University

From recognizing break dancing as a new Olympic sport, to representation in media, to issues of accessibility in our public transit systems, what is something that you can talk about endlessly? What do you care about and why?

Chapman University

What song should we be listening to while reading your application?

University of Georgia

The college admissions process can create anxiety. In an attempt to make it less stressful, please tell us an interesting or amusing story about yourself from your high school years that you have not already shared in your application.


You’ve got a ticket in your hand — Where will you go? What will you do? What will happen when you get there?

California Institute of Technology

Caltech students are often known for their sense of humor and creative pranks. What do you like to do for fun?

Stanford University

Virtually all of Stanford’s undergraduates live on campus. Write a note to your future roommate that reveals something about you or that will help your roommate—and us—get to know you better.

Notre Dame

Defend an unpopular opinion you hold.

Texas Christian University

TCU values individuality and believes that students are more than just a GPA and test score. To help us get to know you even better, consider this opportunity to further express yourself. The only limitations are the boundaries of your imagination. Please upload an essay, poem, work of art or a URL that showcases another side of you.

Elon University

If asked to write a 150-word tweet to tell the world who you are, what would you say?

University of Virginia

We are a community with quirks, both in language and in traditions. Describe one of your quirks and why it is part of who you are.

University of Southern California

If your life had a theme song, what would it be?

Wake Forest University

As part of our “Voices of Our Time” series — which allows students, faculty, and staff to hear from some of the world’s leading thinkers — Wake Forest has hosted Ta-Nehisi Coates, Michelle Alexander, Eboo Patel, and Thomas Friedman. If you could choose the next series speaker, whom would you pick, and why?

University of North Carolina at Chapel Hill

What do you hope will change about the place where you live?

University of Michigan

If you could only do one of the activities you have listed in the Activities section of your Common Application, which one would you keep doing? Why?