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Funny Essay College

We’re not going to lie to you. College essays are scary. For most of our clients, writing their college essay is the most intimidating part of the application process. We get it, and we’ve been there, but we’re here to tell you that, while they might be scary, they’re also an amazing opportunity. So much of the college process is about covering everything in gold leaf and making yourself look as perfect as possible. Contrary to what so many (incorrectly) say, the college essay isn’t about pitching yourself as a perfect person; it’s about being yourself.

A Story

Last year, a student of ours wrote about messing up doing the dishes and got into Penn.

She is a really big people pleaser, almost to a fault, and is always looking for a way to go above and beyond. It’s helped her a lot in life and she came to us with great grades, strong scores, and a vision for her future. But it also made her super cookie cutter. Like you could take her name off of the application and switch in one of any of the other thousands of students with her academic profile and you wouldn’t be able to tell the difference.

The challenge was to show something about her through her essay that gave colleges a peek into what makes her unique – her character, her sense of humor, and her willingness to be the punchline if it’s a good enough joke.

It took a while to tease out a story for the essay, but the one we landed on is a doozy. One day, she was babysitting her brother and decided to go above and beyond by making him dinner. After that went fairly smoothly, she wanted to see the job through by doing all of the dishes. She loaded up the dishwasher, made sure everything was organized and fit right, reached up to the sink, and proceeded to pour dish soap into the detergent dispenser. The result, as you may have already guessed, was a complete and utter disaster. A fun bubble war from the overflowing dishwasher ended in an expensive renovation after soapy water found its way under the hardwood floors.

Penn didn’t love the essay because doing the dishes in inherently interesting or triggering a renovation is an exemplary illustration of collegiate brilliance. Quite the opposite. They loved the essay because the experience of doing the dishes is nearly universal and her mistake was honest and human, so the moment when she puts dish soap where the detergent is supposed to go is easy to visualize and guaranteed to make you cringe. The student was able to take something mundane and normal, and use it as a tool of humanizing herself, giving the admissions officers an opportunity to see behind the stellar grades and scores to the earnest, people pleasing, do-anything-for-family young woman underneath.

We love her as an example of a great essay because she pushed herself to be vulnerable and to be imperfect. She also did an amazing job of following our guidelines for writing an interesting, funny, and unique college essay, which automatically makes her one of our favorites.

Pick a Character Trait

The first step is to pick an aspect of yourself that you want the essay to highlight. For our dishwasher debacle student, the trait was her desire to not just do the job, but to go beyond what’s expected of her. That’s one option, but there are countless options to pick from. Now, it might seem like a fun challenge to try to sell yourself on pessimism and impatience, but this is not the time to try to make greed seem like a good thing. You could highlight kindness, sincerity, determination, persistence, or your passion for cooperative thinking.

If you’re stumped, try texting a few close friends. Ask them what three words they’d use to describe you and start from there. Sometimes what they say will surprise you and it might even give you insight into yourself that triggers an essay-worthy idea.

Don’t Try to Stand Out for the Wrong Reasons

You might think that this is the place to take an outlandish political stance or to try to differentiate yourself from the pack with an essay on how Kylie Jenner is a nuanced example of postmodern modern marketing (also, seriously though, what does that even mean?). We’re here to tell you that it’s not.

The reality is that trying to force depth into a vapid topic that is unrelated to who you are as a person doesn’t show colleges anything about yourself beyond an overestimation of your skills of persuasion. You don’t have a lot of space, so choose something that’s actually worth talking about, that’s personal to you, and that gives them insight into who you.

 Play with the Format

On the subject of space, you have 250-650 words. The only requirement you have to meet is that your essay fits into that space. Other than that you can do almost anything. You can write 40 haikus. You can write a screenplay, a lyric essay, or a poem. You can write a monologue or a comedy scene or a recipe. You can be playful, serious, funny, introspective, or all of the above. You can be like the kid who wrote “Black Lives Matter” over and over (but don’t actually copy that because it was only cool the first time).

No matter the format, your essay needs a beginning, middle, and an end that tells the reader something about yourself that they aren’t getting somewhere else in your application – but part of that ‘telling them about yourself’ can be in the way the essay looks. So have fun with it and give yourself permission to try things that are out of the ordinary, because part of standing out in a positive way is doing something different.

Don’t Use Words You Don’t Use in Real Life

While you’re playing with the format, please please please don’t open up a thesaurus. Seriously, we’re begging you. If you’re trying to say table, say table, and if you want to say “a lot,” say “a lot.” Please don’t pull out plethora, glut, surfeit, or profusion as if you throw them around at lunch.

One reason is that big words that are not in a normal vocabulary are a red flag for essay reviewers. They’re on the lookout for students who are trying too hard and not being their most authentic selves, and dropping ‘superfluity’ like it’s normal is like waving your arm around in class yelling “Me me me! Pick me!” Does that work in class? Probably not. Will it work with your college essay? Same answer.

The second reason is that just because a word comes up as a synonym doesn’t mean that it is perfectly analogous. A good example is the word ‘enigma’ – a current favorite of overachieving college applicants everywhere. As word nerds, we’re the first to admit that it’s a pretty cool word, but it’s also a really complicated word with a nuanced definition that goes beyond ‘confusing’ or ‘puzzling’, the two words we most often see it being substituted in for. Basically, calling yourself, someone else, or something an enigma isn’t going to make you seem fancy in a good way. Keep it simple, clear and use words that you might actually say in a normal conversation.

Want more examples of words you should never use?

Be Who You Are

Even when you’re pushing yourself out of the expected essay format, it’s important to stay true to who you are. We know, we know, taking off the mask is terrifying. You’re never going to get into college if you are honest because who you are is boring and they’re going to see that and everything is going to go wrong and this is a crisis and the world is ending and you should just go hide in a bunker underground. We’ve been there and we’ve gone on that downward spiral, so we’re serious when we say that you’ve got this.

Sometimes, it can take a little practice to get your voice to come out on the page. If you want to show your sense of humor, read some David Sedaris, Mindy Kaling, or Aziz Ansari and see how they land punch lines on paper. If you are more interested in being introspective, re-read your favorite memoir. But even if you look to outside sources for a little inspiration, remember that everything that you need to write a stellar, funny, impressive, and interesting college essay is in you right now. Whether you’re an Ivy League legacy or a first-generation college student, you have it in you tell a powerful, captivating, and admission-winning essay.

 Don’t Put Yourself Down Before You Even Start

Blank pages are scary, but the best way to make them less scary is to fill them with words. Writing is about iteration and patience, and you need to give yourself room and time to explore. Don’t stick yourself in a corner with a simple topic before you’ve even started, and give yourself time to write until you find a subject that clicks. Obviously, this means not waiting until the last minute (we see you procrastinators), but it also means giving yourself permission to not be perfect the first, second, or third time around.

When you make art, not every piece is a masterpiece. The Blue Room is one of Picasso’s most famous pieces, but did you know that it’s actually a painting over a painting? Using fancy modern technology, we know that he actually started off by painting an image of a man in a bowtie. When he decided he didn’t like where it was headed, he let himself start over. What he ended up making is one of his greatest works, and it’s on top of the piece he’d labeled a failure.

Most of us will never be as good at anything as Picasso was at painting, but we can use him as inspiration when it comes to writing. It’s possible that Picasso would never have gotten to The Blue Room if he hadn’t started with that ghostly man, and you’re never going to write a stellar essay if you don’t let yourself start somewhere. 

Take Risks

If you haven’t noticed, there’s a trend to all these tips. The biggest piece of advice that we can give you is that you need to let yourself take risks. You need to be ok with being a little uncomfortable at the beginning and you have to give yourself permission to struggle at first. Writing good essays isn’t easy. It is was, everyone would write one. Writing good essays about yourself is even harder. But you’ve got this; all you have to do is to let yourself get started.


Still stumped? Give us a call, we’re good at this, trust us. 80% of our kids get into their #1 school. We sort of know what we’re doing.

Here’s another one of Dan’s essays. As I got to know Dan better from our almost daily e-mail exchanges, I soon discovered that he had a very sharp sense of humor, in addition to great sensitivity. I encouraged him to take a seemingly mundane event from his life and expose it to his analytical humor. As you’ll see here, he followed my suggestion magnificently:

* * * *
Haircuts and Other Aviation Disasters

I felt the wheels of a cold 747 touch down on my head. I jumped and ran frantically to the bathroom. As I saw the familiar face peering back at me, I felt my stomach sink. There, peering from behind the mirror was Dan, with a brand-new airplane landing strip right down the middle of his head. Another crash landing.

The thing I dislike most in the world is long hair. I don’t mean I dislike the style of long hair or people with long hair. I just dislike long hair on myself. I have very thick, curly hair that lends itself to certain discomforts. Sleeping causes my hair to lodge between the pillow and my skull, which incessantly tugs on my scalp all night long, leaving me with a sore head the next day. Combing proves futile since the comb hooks onto my curls like Velcro and the force required to break through the snarled mass is beyond my pain threshold. Styling products give me headaches. So, I prefer just to crop it all off, as if I’m in Navy boot camp.

This manner of hairstyle seems like a pretty good solution to end all my troubles, doesn’t it? Nope, it’s just a tradeoff. The shorter my hair is, the faster it grows. My hair grows so fast that every two weeks I need another trim just to maintain a bearable length. All I need is someone willing to take five minutes to turn on the clippers and do a few passes over my head. Solution: I let my mom cut my hair.

Having my mom cut my hair is like flying on an airplane. Sure, it’s risky with potential deadly results, but it gets me where I want to go in a short time. But as my mom and the airline industry have proven, out of the many flights from Chicago to New York, there always are a few memorable crashes.

One Sunday morning four years ago, I sat on the barber-chair bucket in the garage for my usual biweekly buzz. The clippers humming above my head sounded like a benign turboprop cruising at 30,000 feet. The gentle buzzing assured me that I wouldn’t have to endure long hair any longer. Everything seemed routine until I felt the sting of what felt like a whirling propeller. My hand instinctively reached toward the trauma site and found a small bare spot. I sprinted to the bathroom mirror and took a small hand mirror from the drawer, angling it so I could see the back of my head.

“And I have school tomorrow!” I shrieked. My mind raced, searching for some covert plan to feign my own death or hitchhike to Canada. After my fanciful plans died in committee, I sequenced some objective logic: “How can I repair this? My hair is black. A ballpoint pen would take off more skin than it would blacken. I need something like . . . a felt marker!” Thus, I proceeded to apply several artful layers of permanent magic marker to my bare spot, and-voila-no more annoying spot.

No one noticed the canyon on the side of my head during the two weeks that it took my hair to grow back. Somehow, I imagined that this experience would serve as an experiential warning and avert future haircut disasters. I was wrong.

This past winter, I once again stood in front of that mirror gazing at yet another calamity. This clear-cut strip would have pleased even the most maniacal lumberjack. It was way too large to repair with markers. So, to compensate, I was forced to shave the rest of my head, since I didn’t really care for the inverted-Mohawk look. Besides that, the Sahara was too far for my coin jar to take me.

That winter I walked around in my big, warm wool sweater complemented by my glistening shaved head. This time, though, EVERYONE noticed. Such is life at Dan’s Barber Shop Airlines.

* * * *

Tip: Titles can lend heft to an essay if they are carefully thought out. After you have finished your final revision and you’re satisfied that your essay can’t get much better, reread it one more time. Look for one or two key aspects that you may be able to work into a title. You can see the results of my title prompting in some of the samples included here.

By the way, Dan was admitted to Yale in April. Bulldogs!

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