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Do any of them strike you immediately as interesting or get you excited and thinking?
You may not have thought of anything like these questions before, but that's okay!
The UChicago supplements are a great chance for you to step back from the typical admissions process, think about something different, and express yourself creatively.
There's no wrong answer or incorrect approach for these prompts.
Be creative, use descriptive language, and have fun!
Remember though, it's more important to make a strong argument with clear thoughts than to write about every sport you've ever played or every place you've traveled.
For example, if I were writing Essay Question #2, I might write about how "I am I and I am my thoughts" and reflect philosophically (maybe include thoughts from philosophers), because I love philosophy (and wanted to study that at UChicago -- and did).If any of these interest you, explain why you think UChicago's flag grants, for example, would help you get a head start on your future research and career goals. Because you're quirky, you love to learn, you spend way too much time falling through the rabbit hole that is Wikipedia, you want to learn Econ from the masters, you...Let your sincere feelings about the college shine through!The second supplemental essay should be much easier than the first, but that doesn't mean you can slack off. Do your research and then explain why the unique aspects of the college make it your top choice.The admissions officers read hundreds of these essays and they see many of the same responses: The Core! The college admissions website is a great place to learn more about what makes UChicago special.The strongest essays will tell a clear story or develop an argument with evidence.The admissions officers will be learning about you by seeing how you construct this argument or how you incorporate characters and language to tell your story.Pick the essay topic that gets you the most excited to write, think, and creatively make an argument or tell a story.For example, I'm most excited about approaching Essay #1, because I love dissecting jokes and think I have some great starting ideas for it, so I would choose that prompt.For the UChicago supplement, you'll have to write two essays: one answering a quirky prompt and the second explaining why you want to go to UChicago. When you take a look at the uncommon essay questions, you should laugh.The essays are meant to be fun, creative, quirky, and thought-provoking.