How do you write a letter to a friend that shows you’re a good candidate for the University of Pennsylvania? What reading list will help the Columbia University admissions committee understand your interdisciplinary interests? How can you convey your desire to attend Yale by inventing a course description for a topic you’re interested in studying?
These are the challenges students must overcome when writing their supplemental essays. Supplemental essays are a critical component of college applications—like the personal statement, they provide students with the opportunity to showcase their authentic voice and perspective beyond the quantitative elements of their applications. However, unlike the personal essay, supplemental essays allow colleges to read students’ responses to targeted prompts and evaluate their candidacy for their specific institution. For this reason, supplemental essay prompts are often abstract, requiring students to get creative, read between the lines, and ditch the traditional essay-writing format when crafting their responses.
While many schools simply want to know “why do you want to attend our school?” others break the mold, inviting students to think outside of the box and answer prompts that are original, head-scratching, or downright weird. This year, the following five colleges pushed students to get creative—if you’re struggling to rise to the challenge, here are some tips for tackling their unique prompts:
University of Chicago
Prompt: We’re all familiar with green-eyed envy or feeling blue, but what about being “caught purple-handed”? Or “tickled orange”? Give an old color-infused expression a new hue and tell us what it represents. – Inspired by Ramsey Bottorff, Class of 2026
What Makes it Unique: No discussion of unique supplemental essay prompts would be complete without mentioning the University of Chicago, a school notorious for its puzzling and original prompts (perhaps the most well-known of these has been the recurring prompt “Find x”). This prompt challenges you to invent a new color-based expression, encouraging both linguistic creativity and a deep dive into the emotional or cultural connotations of color. It’s a prompt that allows you to play with language, think abstractly, and show off your ability to forge connections between concepts that aren’t typically linked—all qualities that likewise demonstrate your preparedness for UChicago’s unique academic environment.
How to Answer it: While it may be easy to get distracted by the open-ended nature of the prompt, remember that both the substance and structure of your response should give some insight into your personality, perspective, and characteristics. With this in mind, begin by considering the emotions, experiences, or ideas that most resonate with you. Then, use your imagination to consider how a specific color could represent that feeling or concept. Remember that the prompt is ultimately an opportunity to showcase your creativity and original way of looking at the world, so your explanation does not need to be unnecessarily deep or complex—if you have a playful personality, convey your playfulness in your response; if you are known for your sarcasm, consider how you can weave in your biting wit; if you are an amateur poet, consider how you might take inspiration from poetry as you write, or offer a response in the form of a poem.
The goal is to take a familiar concept and turn it into something new and meaningful through a creative lens. Use this essay to showcase your ability to think inventively and to draw surprising connections between language and life.
Read More About the UChicago Essays
Harvard University
Prompt:Top 3 things your roommates might like to know about you.
What Makes it Unique: This prompt is unique in both form and substance—first, you only have 150 words to write about all 3 things. Consider using a form other than a traditional essay or short answer response, such as a bullet list or short letter. Additionally, note that the things your roommate might like to learn about you do not necessarily overlap with the things you would traditionally share with an admissions committee. The aim of the prompt is to get to know your quirks and foibles—who are you as a person and a friend? What distinguishes you outside of academics and accolades?
How to Answer it: First and foremost, feel free to get creative with your response to this prompt. While you are producing a supplemental essay and thus a professional piece of writing, the prompt invites you to share more personal qualities, and you should aim to demonstrate your unique characteristics in your own voice. Consider things such as: How would your friends describe you? What funny stories do your parents and siblings share that encapsulate your personality? Or, consider what someone might want to know about living with you: do you snore? Do you have a collection of vintage posters? Are you particularly fastidious? While these may seem like trivial things to mention, the true creativity is in how you connect these qualities to deeper truths about yourself—perhaps your sleepwalking is consistent with your reputation for being the first to raise your hand in class or speak up about a cause you’re passionate about. Perhaps your living conditions are a metaphor for how your brain works—though it looks like a mess to everyone else, you have a place for everything and know exactly where to find it. Whatever qualities you choose, embrace the opportunity to think outside of the box and showcase something that admissions officers won’t learn about anywhere else on your application.
Read More About the Harvard Essays
University of Pennsylvania
Prompt: Write a short thank-you note to someone you have not yet thanked and would like to acknowledge.
What Makes it Unique: Breaking from the traditional essay format, this supplement invites you to write directly to a third party in the form of a 150-200 word long letter. The challenge in answering this distinct prompt is to remember that your letter should say as much about you, your unique qualities and what you value as it does about the recipient—all while not seeming overly boastful or contrived.
How to Answer it: As you select a recipient, consider the relationships that have been most formative in your high school experience—writing to someone who has played a large part in your story will allow the admissions committee some insight into your development and the meaningful relationships that guided you on your journey. Once you’ve identified the person, craft a thank-you note that is specific and heartfelt—unlike other essays, this prompt invites you to be sentimental and emotional, as long as doing so would authentically convey your feelings of gratitude. Describe the impact they’ve had on you, what you’ve learned from them, and how their influence has shaped your path. For example, if you’re thanking a teacher, don’t just say they helped you become a better student—explain how their encouragement gave you the confidence to pursue your passions. Keep the tone sincere and personal, avoid clichés and focus on the unique role this person has played in your life.
Read More About the UPenn Essays
University of Notre Dame
Prompt: What compliment are you most proud of receiving, and why does it mean so much to you?
What Makes it Unique: This prompt is unique in that it invites students to share something about themselves by reflecting on someone else’s words in 50-100 words.
How to Answer it: The key to answering this prompt is to avoid focusing too much on the complement itself and instead focus on your response to receiving it and why it was so important to you. Note that this prompt is not an opportunity to brag about your achievements, but instead to showcase what truly matters to you. Select a compliment that truly speaks to who you are and what you value. It could be related to your character, work ethic, kindness, creativity, or any other quality that you hold in high regard. The compliment doesn’t have to be grand or come from someone with authority—it could be something small but significant that left a lasting impression on you, or it could have particular meaning for you because it came from someone you didn’t expect it to come from. Be brief in setting the stage and explaining the context of the compliment—what is most important is your reflection on its significance and how it shaped your understanding of yourself.
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Stanford University
Prompt: List five things that are important to you.
What Makes it Unique: This prompt’s simplicity is what makes it so challenging. Stanford asks for a list, not an essay, which means you have very limited space (50 words) to convey something meaningful about yourself. Additionally, the prompt does not specify what these “things” must be—they could be a physical item, an idea, a concept, or even a pastime. Whatever you choose, these five items should add depth to your identity, values, and priorities.
How to Answer it: Start by brainstorming what matters most to you—these could be values, activities, people, places, or even abstract concepts. The key is to choose items or concepts that, when considered together, provide a comprehensive snapshot of who you are. For example, you might select something tangible and specific such as “an antique telescope gifted by my grandfather” alongside something conceptual such as “the willingness to admit when you’re wrong.” The beauty of this prompt is that it doesn’t require complex sentences or elaborate explanations—just a clear and honest reflection of what you hold dear. Be thoughtful in your selections, and use this prompt to showcase your creativity and core values.
Read More About the Stanford Essays
While the supplemental essays should convey something meaningful about you, your values, and your unique qualifications for the university to which you are applying, the best essays are those that are playful, original, and unexpected. By starting early and taking the time to draft and revise their ideas, students can showcase their authentic personalities and distinguish themselves from other applicants through their supplemental essays.
Originally posted on Forbes.
