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Our Top 10 Most Mind-Blowing Supplemental Essay Prompts

One of our favorite things about this time of the year is tracking the release of supplemental essay prompts. (Check out our database for the most-up-to date list). While many schools stick to classical questions about academic interests and extracurricular involvements, others get a bit more creative and bold. Depending upon the particular college or university, students could find themselves creating personal hashtags, collecting the soundtrack of their lives, or even explaining how Olive Garden can possibly offer unlimited breadsticks.  

Many college admissions blogs have collected their favorite quirky supplemental essay prompts, but here at DC College Counseling, we like to write “outside the box”- just like we encourage our students to do. So in the spirit of creativity, we’re sharing our top 10 list of most mind-blowing supplemental essay topics.

Top 10 List

We’re so inspired by Wake Forest’s infamous ‘Top 10’ that we couldn’t help but answer their prompt in our blog today. For years, applicants have been challenged to create a top 10 list for the admissions team. Any theme, any topic, any concept goes! With no limitations, this prompt all-but-begs for creative risk-taking. A generic collection of favorite foods or best movies of all time won’t cut it here. Students have to stretch their imaginations if they want to move to the top of Wake’s list.

A Mouthful of Advice

UChicago is famous for its eccentric supplemental essay topics. In the past, applicants  have been asked to ponder deep questions like “Where is Waldo, really” and “​​What is square one, and can you actually go back to it?”  

So who comes up with these quirky topics? UChicago actually takes suggestions from its own student body to craft their five annual prompts. Although the essay topics change dramatically from year to year, one thing remains the same. Choice six, otherwise known as “choose your own adventure” allows applicants to select any essay prompt from a previous UChicago admissions cycle.

The 2023 prompts have just been released, and we think this one is a real mind bender: what advice would a wisdom tooth have?  Students better brush up on their personification skills if they want to get at the root of this question.

A geographic conundrum

If you follow us on social media, then you probably know by now that the University of Virginia completely overhauled their supplemental essay topics for the 2022-2023 cycle. Gone are the days of the 250 word essays. As part of the application, students are now required to choose from a list of 11 topics and write two- 50 word responses. Sounds easy, right? Well, not exactly. Some of the prompts are definite brain teasers. Just take a look at choice #9: tell us about a place you’d like to share with everyone, but also keep to yourself. Tackling an antithetical prompt like this one is going to be an exercise in irony and ingenuity, that’s for sure.

Ice cream, anyone?

Cleverly capitalizing on its location, UVM took inspiration from Burlington entrepreneurs Ben and Jerry for one of its supplemental essays. Last year, applicants had 500 words to reflect on the Ben and Jerry’s ice cream flavor- real or imagined- that best describes them.

This was definitely one of our favorite fun topics in the 2022 cycle, but we know it caused a brain freeze for some student writers. With over 100 Ben and Jerry’s flavors to choose from, many applicants were left wondering: what do caramel swirls and brownie bits really say about me?

Tell the truth!

What is the truest thing that you know? This has been Villanova University’s philosophical take on supplemental essays for the past few years. And yes, the truth will continue to prevail this admissions cycle. Applicants who select this prompt from the list of five choices will have to grapple with some deep concepts if they want to produce a meaningful response. What exactly is the truth? Where can you find it? And what do you do with the truth once you discover it? Then they’ll have to capture all of this contemplation succinctly in 250 words. 

So in conclusion, the truest thing we know is: this essay question looks deceptively simple, but it’s actually the most mind-blowing prompt on Villanova’s supplemental essay list.

Anything Goes!

Some schools have very structured topics and guidelines, but that’s not the case at The College of William and Mary. Here “anything goes” –well, anything except a boring response. For years, W&M  has prompted applicants to explain what makes them unique and colorful —and with “attitude.”  As if this isn’t enough of a creative challenge, the admissions team proclaims, “Inspire us, impress us, or just make us laugh!” 

To captivate their audience, student writers have to abandon their formal academic tones and inject their essays with much more character and flair! We know this is a real mindbender for those who haven’t thought much about writing style before, but there’s a lot of fun to be had in this personality-promoting essay.  Remember, anything goes–if W&M sticks with the same prompt this admissions cycle. Wait and see!

A picture is worth a thousand words

Rice University has a reputation for quirky traditions, and one just happens to appear in the admissions application. In addition to supplemental essays, applicants must also submit an image of something that appeals to them. This space is affectionately referred to as “the box.”

Now uploading a photo might seem much quicker and easier than writing another essay. However, many of our students have admitted to spending more brainstorming hours on this prompt than the essays themselves. After all, the picture has to speak for itself because no captioning is permitted. And it better say something truly original about the applicant!

Would you like fries with that?

Last year Pomona College posed a seemingly silly question to applicants: what’s your favorite way to eat a potato? Mashed? Hashed? Fried? The most mind-blowing part of this prompt for some might have been wondering why the admissions team thought applicants needed 50 whole words to answer it. However, for some, this became a deep and thoughtful question. Why, you might ask? Well, because every single supplemental question is a chance for applicants to reveal something deeper about themselves, no matter how you slice or mash it.

Have a little heart

In 2019, Notre Dame added a bit more heart to the standard ‘why this school’ supplemental essay.  For the past three admissions cycles, applicants have been asked: how do you hope a Notre Dame education and experience will transform your mind and heart? 

With a soulful side to the prompt, a powerful verb like transform, AND a strict word limit, it’s no wonder students have been stumped by the question. The wording can easily trick applicants into writing vague responses about critical thinking and kindness. Really, though, the heart of this prompt is still ‘why this school.’ In 200 words or fewer, students need to show they’ve done their homework on Notre Dame and understand how the school will help them grow personally and academically. This tricky prompt definitely requires a fighting Irish spirit to prevail, especially if it appears again on the application this year.

A Wonderful Essay

Did you know that Dr. Seuss is a Dartmouth alumni? The college is honoring the famous author this admissions cycle in one of its supplemental essay prompts: Dr. Seuss, aka Theodor Geisel of Dartmouth’s Class of 1925, wrote, “Think and wonder. Wonder and think.” What do you wonder and think about?

Studies have found that we have about 6,000 thoughts per day. So how does an applicant choose just one to discuss in their application essay? We’re guessing that the more student writers wonder about their thoughts for this prompt, the more thoughts they’ll continue to generate. And so the Dr. Seuss cycle goes…which doesn’t exactly make writing this 250 word essay easy. 


Need help with supplemental essays?

Book a session with us here. We have a team of essay coaches ready to help students craft strong, memorable responses!