5 Strategies for UChicago Quirky Essays: From Giraffes to Tartufo, How to Write with a Where Fun Goes To Die Mind

Published on May 14, 2026

Every August, when UChicago releases its supplement prompts, it is both the day I look forward to most and the day that gives me the biggest headache.

I look forward to it because UChicago's prompts are the most creative, most quirky, and most intellectually demanding supplemental essay questions in the United States. I get a headache because 80% of students read them and have absolutely no idea where to begin.

2024-25 UChicago Prompt #4 example:"Don't be afraid of the long, long word. It's a way of speaking. The longer the word, the more enthusiastic the speaker." Write an essay in defense of one specific, very long word. — Inspired by Tate Murch, AB'26

Or a classic example:"If a giraffe attends class on Mondays, Wednesdays, and Fridays, what does it study?"

A student's first reaction is usually: "Is this a real prompt? How am I supposed to write this?"

After 15 years of guiding UChicago applicants, my answer is always the same: UChicago quirky essays are not testing creativity; they are testing mind-on-mind quality. Can your mind open a five-kilometer-long trail of thought from an absurd proposition? This article uses 5 key strategies plus analysis of real 2024-25 prompts to show you how to make an admissions officer finish your essay and think, "This student's mind is fascinating. Admit."

1. What Are UChicago Quirky Essays: The Outlier Among Supplements

UChicago's supplemental essay structure:

The Extended Essay is UChicago's signature. Each year, 5-6 prompts are proposed by UChicago students and alumni, then selected by admissions. Their classic status in undergraduate applications is practically the Coachella of essay prompts.

The essence of the UChicago Extended Essay: it filters for a particular kind of mind: someone who can play with an absurd premise and still produce intellectual depth.

2. The Student UChicago Wants: Life of the Mind

UChicago's admissions culture can be summed up in one phrase: Life of the Mind: learning for the joy of it, treating argument as daily life, studying without reducing everything to utility.

The Extended Essay is UChicago's mechanism for filtering for this kind of mind. If a student writes it well, the admissions officer knows they belong here. If they write it poorly, the problem is not just that the essay is weak; it is that the whole person may not fit.

After 15 years in practice, I have found this: students who cannot write a UChicago Extended Essay would probably be miserable at UChicago too. This essay is a two-way filter.

3. Strategy 1: Choose the Right Prompt, the One That Matches Your Spike

UChicago gives 5-6 prompts each year and asks you to choose 1, plus Prompt 6, the "choose your own question" option (strongly not recommended, explained later).

Criteria for choosing a prompt:

Breakdown of the 5 UChicago 2024-25 prompts:

Prompt 1: "We're all familiar with green-eyed envy or feeling blue, but what about being 'caught purple-handed'?..."

• Best for: humanities / language / psychology / interdisciplinary spikes
• Ceiling: students who can show linguistic sensitivity

Prompt 2: "Lots of language has lost the spice it once had..."

• Best for: linguistics / history / philosophy spikes
• Ceiling: a short essay on the evolution of language

Prompt 3: "Despite their origins in the Gem State or the Garden State..." (the 2023 stereotype prompt)

• Best for: any spike; the key is argumentative ability
• Ceiling: writing something that reads like an op-ed in The Atlantic

Prompt 4: "Don't be afraid of the long, long word..."

• Best for: literature / language / cultural studies spikes
• Ceiling: defending a supercalifragilisticexpialidocious-level long word

Prompt 5: Usually a "Mash-up / interdisciplinary" prompt

• Best for: interdisciplinary spikes, double-major ambition, unusual combinations
• Ceiling: weaving 2 seemingly unrelated fields into one essay

Prompt 6: "Pose your own question..."

• Do not choose it. More on this later.

Rule: Within 24 hours of the prompts being released, write 5 brainstorm bullets for each prompt. The prompt for which you can produce 10+ bullets is your choice.

4. Strategy 2: Worldbuild Before Writing: Construct the Universe First

The biggest difference between the UChicago Extended Essay and the Common App PS: it does not want a narrative; it wants a universe.

The PS is a story. The Extended Essay is an entire mental world you want to bring the admissions officer into.

The first step when I guide students through the Extended Essay: Worldbuilding workshop.

Iron rule: Before you write the first word, you need 3 lines of answers for each of these 7 questions. An Extended Essay without enough worldbuilding cannot reach 1,000 words. You will get stuck at 400 words because your mind has no material.

Example: A student chose Prompt 4, defending a long word. The word was "Floccinaucinihilipilification" (from Latin, meaning "the act of estimating something as worthless"). The worldbuilding looked like this:

• Etymology: a 17th-century Latin booklet from Eton College
• Anti-logic: using a 29-letter long word to describe "worthlessness" is itself a contradiction
• Personal touchpoint: the student's father is an accountant who often judged the student's interests as having "no practical value"
• Interdisciplinary cousins: the economic idea of "negligible quantity," and emptiness in Buddhism
• Pushed to the extreme: how would society function if everything were subject to floccinaucinihilipilification?
• If it disappeared: without this act, everything would be "worthwhile," which is also absurd
• 2026: in the age of AI, human judgment of "value" is being reshuffled

These 7 answers are already enough for a 1,200-word essay.

5. Strategy 3: Don't Be Afraid of Weird: What the Tartufo Essay Teaches Us

One of the most famous Extended Essays in UChicago history is The Tartufo Essay.

In 2014, a student admitted to UChicago chose the prompt "Where's Waldo, really?" She wrote a 1,200-word essay about Tartufo, the Italian truffle dessert, beginning in her grandmother's kitchen in Naples, winding into Italy's postwar economy, then into language (why truffles are called tartufo in Italian), then into a melted piece of Tartufo in her family's suitcase when they moved to the United States.

The essay never mentioned Waldo once. But by the end, the admissions officer understood: Waldo is not in a particular place on a map. Waldo is in the process of looking for him.

What this essay teaches us:

Iron rule: By the middle of your Extended Essay, you should start to feel afraid: "Is it really okay to write this?" That fear is a signal that you are writing in the right direction. If you finish the essay and feel no discomfort at all, it is probably too safe, and the admissions officer will not remember it.

6. Strategy 4: End with a "So What" Insight: The Wisdom of Landing the Essay

The most common failure mode in UChicago Extended Essays: the beginning is weird, but the ending turns into a lecture.

A student writes 1,000 words of imaginative thinking about a giraffe attending school on Mondays, Wednesdays, and Fridays, and then the last paragraph says:

"Ultimately, this thought experiment teaches us that creativity requires us to think outside the box and embrace the unexpected. In college, I hope to continue exploring such ideas..."

That is an immediate rejection.

UChicago's "so what" insight must meet these standards:

Side-by-Side Example

Bad ending:

The giraffe attending Monday-Wednesday-Friday classes teaches us that learning happens in unexpected ways. I look forward to bringing this curiosity to UChicago.

Good ending:

The giraffe doesn't go to class Tuesdays and Thursdays because his neck is too long for the lab benches. Sometimes the answer to a question isn't pedagogical—it's architectural. Maybe the question we should be asking isn't what the giraffe studies, but who designed the room so that he couldn't.

The difference: the good version brings the essay's weird thinking back to a concrete physical problem and opens a genuinely intellectual observation: our blind spots around accessibility are structural, not individual.

7. Strategy 5: Keep Your Voice Consistent: Do Not Pretend to Be Someone Else

Because the UChicago Extended Essay can run 1,000+ words, voice consistency is a life-or-death issue.

Iron rule: After you finish, read it aloud. If any sentence makes you feel, "This does not sound like something I would say," delete it.

One student I worked with, R, who was ultimately admitted to UChicago Class of 2027, wrote her Extended Essay on Olive Garden breadsticks and the paradox of finite matter in the universe. Across 1,300 words, her voice was so consistent that after reading it, you wanted to know where the Olive Garden near her house was. That is the kind of voice that got her admitted.

8. Sample Angles for Real 2024-25 Prompts

Using the 2024-25 Prompt 1 ("caught purple-handed"), here is what a brainstorm of possible angles might look like:

Prompt 1: "We're all familiar with green-eyed envy or feeling blue, but what about being 'caught purple-handed'? Or some other color we don't usually associate with a particular emotion? Create a color-emotion pairing, and tell us what kind of situation might give rise to it."

Angle 1 (linguistics): Why does English use "red" for anger ("seeing red"), while another culture might use green to signal infidelity or shame? Invent a color-emotion pairing: pale beige = misunderstood achievement. Write a beige moment: you win silver at a science fair, your whole family celebrates, but you know the judges misread your chart.

Angle 2 (science): Colors outside the visible spectrum for the human eye, such as infrared and ultraviolet, correspond to emotions the human brain cannot quite perceive. For example, "infrared feeling" is unspeakable shame, while "ultraviolet feeling" is regret for something that has not happened yet.

Angle 3 (family history): Your grandmother had a habit of using 6 different apron colors for 6 moods. Every color had a story. You invent the 7th: ochre = wanting to cry but not crying, because it was the color of her final apron, the one she never had the chance to wear.

Angle 4 (philosophy): Color perception is culturally constructed (Homer had no word for "blue"), so are emotions culturally constructed too? Invent an emotion: "homerness": the longing for a feeling that has not yet been named.

Angle 5 (self): You are colorblind. The "green" you see is not the green other people see. What color, then, is your "green-eyed envy" to everyone else?

These 5 angles: any one of them could become an outstanding Extended Essay. But if you can choose the one closest to your spike, you win.

9. Prompt 6, Choose Your Own Question: Why You Should Not Choose It

Every year, UChicago's final prompt is: "Pose your own question and answer it."

This prompt looks free, but it is actually a trap.

Why?

Exception: if your essay idea absolutely cannot fit into prompts 1-5, then you may choose Prompt 6. But among the 200+ UChicago applicants I have advised over 15 years, only 3 truly needed Prompt 6.

Conservatively choose 1-5. They are the stage UChicago has designed for you. Go dance on it.

10. Word Count Strategy: How Long Should It Be?

The UChicago Extended Essay has no word limit. The most common student question is: "Will 1,500 words be too long?"

Answer: Length itself does not matter. Density does.

Density test: Does every 100 words contain 1 specific image / fact / quote? If not, the writing is watery.

11. Voice Example: What Does a Strong UChicago Essay Sound Like?

Look at the opening of a real UChicago Extended Essay. The student chose the prompt: what can actually be divided by zero?

Division by zero is the mathematical equivalent of asking a five-year-old to tell you about her day. The question is well-formed; the inputs are valid; and yet the answer expands without bound, swallowing the entire afternoon, the cat's name, and a story about Hanna who took her glitter pen at recess. Mathematicians call this "undefined." My mother calls it Tuesday. >I want to defend the proposition that one thing can, in fact, be divided by zero: a Wednesday afternoon at my grandmother's apartment in Kaohsiung. I have evidence. The first piece of evidence is the smell...

Breakdown:

• Sentence 1: connects an abstract math concept to a concrete mundane scene, a five-year-old talking
• Sentence 2: gives specific details, the cat's name and Hanna's glitter pen
• Sentence 3: contrasts two systems, mathematician vs. mother
• Sentence 4: smash cut to the thesis, Wednesday at grandmother's apartment
• Sentence 5: promises evidence to come, hooking the admissions officer

The voice of the whole passage: smart, self-deprecating, culturally bilingual, structurally loose but precise. This is the kind of mind UChicago wants to see.

12. Conclusion: UChicago Is Built for People with Weird Minds

After 15 years in practice, this is the final reminder I give every UChicago applicant:

When writing the UChicago Extended Essay, do not try to "get into UChicago"; try to "think like a UChicago student."

UChicago does not want well-rounded, polished, perfectly safe students. They want people who are a little weird, a little sharp, a little obsessive, and a little lost in a particular idea.

If the admissions officer finishes reading and thinks, "This student will tear apart Plato's argument in the first Hum 110 class," you have won.

Do not fear weirdness. Do not fear digression. Do not fear making the admissions officer think in paragraph three, "Wait, what are they writing about?" As long as you can bring it back, that is the UChicago essay.

Hidden inside 1,200 words is a life of the mind. Where fun goes to die, actually means where fun goes to evolve.

Further Reading:

• How to Write the 650-Word Common App Personal Statement
• How to Research a School for a Strong Why University Essay
• How to Write Stanford's Roommate Letter
• How to Write MIT's Short Answers
• How to Use Additional Information Effectively
• Complete Profile of UChicago, the University of Chicago