Writing the college essay
How do you write a letter to a friend showing that you are a viable candidate for the University of Pennsylvania? What reading list will help Columbia University’s admissions committee understand your interdisciplinary interests? How can you express your desire to attend Yale by inventing a course description for a subject you want to study?
These are the challenges students must overcome when writing their supplemental essays. Supplemental essays are an important part of college applications—like the personal statement, they provide students with an opportunity to showcase their authentic voice and perspective beyond the quantitative elements of their applications. Unlike the personal essay, however, supplemental essays allow colleges to read students’ responses to targeted prompts and evaluate their suitability for their respective institution. Because of this, supplemental essay prompts are often abstract and require students to get creative, read between the lines, and abandon the traditional essay format when composing their responses.
While many schools simply want to know “why you want to attend our school,” others break the mold and ask students to think outside the box and respond to questions that are original, confusing, or just plain weird. This year, the following five colleges asked students to get creative—if you’re struggling to rise to the challenge, here are some tips for handling their unique questions:
University of Chicago
Prompt: We all know envy and sadness, but what about being “caught red-handed”? Or “overjoyed”? Give an old, colorful 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 essay topics would be complete without mentioning the University of Chicago, a school known for its enigmatic and original themes (the most famous of which is probably the recurring “find x” theme). This topic asks you to invent a new color-based expression and encourages both linguistic creativity and a deep dive into the emotional or cultural connotations of color. It’s a topic that allows you to play with language, think abstractly, and show your ability to make connections between concepts that aren’t normally linked—all qualities that also demonstrate your preparation for UChicago’s unique academic environment.
How to answer the question: While you may be easily distracted by the open-ended nature of the question, remember that both the content and structure of your answer should provide insight into your personality, perspective, and characteristics. Start with this in mind by thinking about the emotion, experience, or idea that most resonates with you. Then let your imagination run wild and consider how a particular color might represent that feeling or concept. Remember that the question is ultimately an opportunity to show your creativity and original way of looking at the world, so your explanation doesn’t have to be unnecessarily deep or complex—if you have a playful personality, express that playfulness in your answer; if you’re known for your sarcasm, consider how you can incorporate your biting wit; if you’re an amateur poet, consider how you might get inspiration from writing poetry or provide an answer in the form of a poem.
The goal is to transform a familiar concept into something new and meaningful through a creative lens. Use this essay to demonstrate your ability to think inventively and make surprising connections between language and life.
Harvard University
Prompt: The three most important things your roommates might want to know about you.
What Makes It Unique: This prompt is unique in both form and content—first, you only have 150 words to write about all 3 things. Consider using a form other than a traditional essay or short response, such as a bulleted list or short letter. Also, keep in mind that the things your roommate may want to know about you won’t necessarily overlap with the things you’d normally tell an admissions committee. The goal of the prompt is to get to know your quirks and weaknesses—who are you as a person and as a friend? What sets you apart outside of academic achievements and accolades?
How to answer the question: First of all, you can get creative in answering this question. As you write a supplementary essay and, therefore, a professional piece of writing, the question will prompt you to share more personal qualities, and you should try to demonstrate your unique characteristics in your own voice. Think about things like: How would your friends describe you? What funny stories do your parents and siblings tell that embody your personality? Or consider what someone would want to know about living with you: Do you snore? Do you have a collection of vintage posters? Are you particularly meticulous? While these may seem like trivial things, the real creativity lies in how you connect these qualities to deeper truths about yourself—perhaps your sleepwalking fits with your reputation for always being the first to raise your hand in class or standing up for a cause you care about. Perhaps your living conditions are a metaphor for how your brain works—even though it looks like chaos to everyone else, you have a place for everything and know exactly where to find it. Whatever qualities you choose, take the opportunity to think outside the box and highlight something that admissions officers won’t see anywhere else in your application.
University of Pennsylvania
Prompt: Write a short thank you message to someone you haven’t thanked yet and would like to thank.
What makes it unique: This supplement breaks from the traditional essay format and asks you to write a 150-200 word letter directly to a third person. The challenge in answering this particular 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 without seeming overly boastful or contrived.
How to respond: When choosing a recipient, think about the relationships that most shaped your high school years. Writing to someone who played a big role in your story will give the admissions committee insight into your development and the meaningful relationships that guided you along the way. Once you’ve identified the person, craft a thank-you letter that’s specific and heartfelt. Unlike other essays, you’re invited to be sentimental and emotional in this prompt, as long as it authentically expresses your gratitude. Describe the impact this person had on you, what you learned from them, and how their influence 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. Make sure your tone is sincere and personal, avoid cliches, and focus on the unique role this person played in your life.
University of Notre Dame
Prompt: What compliment are you most proud of and why does it mean so much to you?
What makes it unique: This prompt is unique in that it asks students to share something about themselves by reflecting on another person’s words in 50-100 words.
How to answer it: The key to answering this prompt is to not focus too much on the compliment itself, but instead focus on your reaction to it and why it was so important to you. Note that this prompt is not an opportunity to brag about your accomplishments, but rather to show what really matters to you. Choose a compliment that truly expresses who you are and what you value. It could be about your character, work ethic, kindness, creativity, or another quality you hold in high regard. The compliment doesn’t have to be grand or come from an authority figure—it could be something small but significant that left a lasting impression on you, or it could have special meaning to you because it came from someone you weren’t expecting it. Be brief when setting the stage and explaining the context of the compliment—what matters most is your reflections on its meaning and how it shaped your self-image.
Stanford University
Prompt: List five things that are important to you.
What makes it unique: The simplicity of this prompt is what makes it so challenging. Stanford requires a list, not an essay, which means you have very limited space (50 words) to say something meaningful about yourself. Additionally, the prompt doesn’t dictate what those “things” must be—it 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 the question: Start by brainstorming what matters most to you—this could be values, activities, people, places, or even abstract concepts. The key is to choose things or concepts that, when considered together, provide a comprehensive overview of who you are. For example, you might choose something tangible and concrete like “an antique telescope given to me by my grandfather” alongside something conceptual like “a willingness to admit mistakes.” The beauty of this question is that it doesn’t require complex sentences or lengthy explanations—just a clear and honest representation of what matters to you. Think carefully about your choices, and use this question to showcase your creativity and core values.
While supplemental essays should convey something meaningful about you, your values, and your unique qualifications for the university you are applying to, 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 show their authentic personality and stand out from other applicants through their supplemental essays.
