So, in our last article in this set, we talked a bit about some strange essay prompts, and how you could deal with them.

So, in our last article in this set, we talked a bit about some strange essay prompts, and how you could deal with them. This time around, we're going to talk about some more, but with a bit more of a focus on just plain tough ones.

Sure, it can be a bit of a whopper when you encounter a question like, "How do cheese and play-dough factor into your decisions about college admissions?", but it can be just as much of an issue when you stumble into "Based on what Plato wrote in the 8th word of the 3rd line of the 10th page of Phaedo, please explicate the meaning of Winston Churchill when he said, 'I am fond of pigs. Dogs look up to us. Cats look down on us. Pigs treat us as equals.'" (Admittedly, that last one is pretty strange all on its own, but hopefully you catch my drift.)

Some questions are just difficult, and we're going to kit you out with the tools you need to crack 'em. 

If you want even more assistance, then you should check out EssayEdge, with its array of expert essay editors! 

French novelist Anatole France wrote: "An education isn't how much you have committed to memory, or even how much you know. It's being able to differentiate between what you do know and what you don't." What don't you know?
- Brown University

If you were to develop a Mt. Rushmore representing the 20th century, whose faces would you select and why?
- William and Mary

Sartre said "Hell is other people," while Streisand sang, "People who need people are the luckiest people in the world." With whom do you agree?
- Amherst College

It has been said [by Andy Warhol] that "in the future everyone will be famous for fifteen minutes." Describe your fifteen minutes.
- New York University

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These questions give you everything you need to answer them, really. They're clear, and precise, and intelligible. None of which does anything to ameliorate the fact that after reading them, you can still be sitting there, stumped, utterly unsure of what direction to take the question in. "What don't I know?" you'll be asking yourself. "Whose faces would go on the new Mt. Me-more?" "Who are the luckiest people?" "What would my fifteen minutes be?"

There's a key technique to help you knock out these questions: brainstorming. Just put your fingers on the keyboard (or, if you're old-fashioned, put pen to paper), and start writing some ideas. Don't worry about their quality; just get something out there. And once you've got a screen (or paper) full of ideas, then you can start whittling them down to your favorites. And then, once you've got your favorites, you can whittle some more, to the absolute best. And so on.


What would you do with a free afternoon tomorrow?
- Yale University

If you could balance on a tightrope, over what landscape would you walk? (No net.)
- University of Chicago

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Here, it's not about academic knowledge, or parsing nigh-inscrutable questions, or anything of the nature. It's all about you. These questions are designed to give you an opportunity to talk about yourself, albeit in an indirect way. That way, you can talk about yourself all you want without feeling awkward about it!

Of course, that's not an excuse to lose your wit. What's going to make you stand out in these questions is tackling them cleverly and uniquely. The questions are about you, after all; so make them really about you, down to every word. Not an easy task, but if you can pull it off, it'll pay off in spades.


UChicago professor W. J. T. Mitchell entitled his 2005 book What Do Pictures Want? Describe a picture, and explore what it wants.
- University of Chicago

Spanish poet Antonio Machado wrote, "Between living and dreaming there is a third thing. Guess it." Give us your guess.
- University of Chicago

University of Chicago alumna and renowned author/critic Susan Sontag said, "The only interesting answers are those that destroy the questions." We all have heard serious questions, absurd questions, and seriously absurd questions, some of which cannot be answered without obliterating the very question. Destroy a question with your answer.
- University of Chicago

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Tough questions, these. They sound like they're simple enough when you read them to yourself, but then you think about them and realize that it's a bit more complicated. How do you figure out what a picture wants, or what is between living and dreaming? How the heck do you destroy a question?

The brainstorming tip from above still applies, but these questions have less to do with just coming up with a list of possible answers and whittling down until you get to your favorites. What these questions are really about, most likely, are how you answer, and not necessarily as much what you answer.

You obviously can't throw out a silly or empty answer, so don't disregard the "what". But whatever you choose to answer with, explain yourself and your reasoning cogently and coherently. That's the key with these questions. Make sure that your reader will understand not only exactly what it is you're saying, but why it is that you're saying it. And if you can, make it a fun read, while you're at it. That's extra points.


Science, math and society are filled with postulates, laws and theories like the Ninth Commandment, PV=nRT, Occam's Razor and H.R. 3541. Warm air rises. Good (English) grammar requires "i" before "e" except after "c." So pick a law, any law, and explain its significance to you.
- Tufts

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Simple tip here. Don't pick the obvious. Brainstorm (just like the earlier tip! These things actually come in handy!) and come up with a whole of mess of possibilities for a question like this. When you're narrowing your list, keep in mind that originality can do a whole lot to make your essay memorable and enjoyable. For the question above, you have every law ever written, from science to government to math to ANYTHING. Don't limit yourself here. Go with what feels right to you, and of course choose something you can actually write about. But pick something that's really going to represent you. 


Elvis is alive! Okay, maybe not, but we have been persuaded that recent Elvis sightings in highway rest areas, grocery stores and laundromats are part of a wider conspiracy involving five of the following: the metric system, the Mall of America, the crash of the Hindenberg, Heisenberg's uncertainty principle, lint, J.D. Salinger, and wax fruit. Construct your own theory of how and why five of these items are related.
- University of Chicago

The late William Burroughs once wrote that "language is a virus from outer space." We at the University of Chicago think he's right, of course, and this leaves us wondering what else came here with it. Could this finally explain such improbable features of modern life as the Federal Tax Code, non-dairy creamer, Dennis Rodman, and the art of mime? Name something that you assert cannot have originated any other way. Offer a thorough defense of your hypothesis for extraterrestrial origins, including alternate explanations and reasons for eliminating them from consideration.
- University of Chicago

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Story time! These last two questions are asking for nothing so much as they're asking for you to tell a fun, fascinating, and well-written story. And that last point is probably the most important: well-written. Yes, you need to construct an entire piece that fits together well, but at the same time, the questions themselves are pointing at fun and humor. So have fun with them, while still bringing all of your intelligence and writing skill to bear. 

Got any good college essay questions you've encountered? Or any good tips for people writing college essays? Share with us on our Facebook page!