What are some unique prompts you've encountered for college essays and how did you approach them?

These unique prompts can definitely feel tricky at first, but they’re also great opportunities to let your personality come through in ways standard essays sometimes don’t allow. I’ve seen prompts like “What advice would you give to your past self?” or “If you could invent a holiday, what would it celebrate?” Some colleges like UChicago are especially known for their offbeat, creative questions—one year they had, “How are apples and oranges supposed to be compared?”

For brainstorming, my first step is always to jot down the first ideas that come to mind—even if they seem silly or random. Weirdly enough, these initial gut reactions often contain something personal or memorable. For the historical figure advice prompt, I might start by picking someone I genuinely admire, then ask myself: what challenges did they face that parallel something in my own life? Maybe I’d choose Ada Lovelace, and write a letter about self-doubt as a woman interested in STEM, which ties back to my own experience joining the robotics team.

For roommate letters, I’d focus less on listing traits or favorite snacks and more on how I interact with people in shared spaces. For instance, I once wrote about how I like to hang up indie band posters and host impromptu tea parties—using anecdotes to quickly showcase quirks and values. If you’re naturally funny, don’t be afraid to use humor, but only if it feels genuine (forced jokes can fall flat). If a prompt invites reflection, honesty often wins—vulnerability, when handled thoughtfully, tends to resonate with readers.

My process always includes asking myself: what does this say about me that isn’t already in the rest of my application? I try to keep it focused on one or two vivid examples so my essay remains memorable. And trust your instincts—if an essay feels a little scary or exposes a truth about you, that’s usually a good sign.

Don’t be afraid to get creative, but anchor your responses in real experiences or honest insight. It’s not about choosing the most unusual angle, but about picking one that authentically reflects your voice. For example, describing how your habit of naming your plants after famous poets actually reflects your curiosity and love of language can be a fun and revealing answer!

Ultimately, unique prompts are invitations for you to surprise the reader—with creativity, self-awareness, or humor. Trust that being authentic and specific is what really makes your essay stand out.