How to Improve Your Wit

Doing Your Research

Learn about types of wit. There are a couple related but different ways to think about the idea of wit, and many different ways to express it. Before you get started, consider what "improving your wit" means to you. A manner of speaking that is amusing because it is surprising and clever: Probably the most common use of the word today, this is what people generally mean when they speak of, “being witty.” One’s general intellectual faculties; ability to reason; mental capacity: As in, “to keep one’s wits about one,” “natural wit,” “to have the wit to,” or “dim-witted.” Facility with words; deft use of language: As in, "witty banter." Aphorism: A short saying that seem to encapsulates a general truth. Examples include, “Wise men don't need advice; fools don't take it” (Benjamin Franklin), and “Beauty is only skin deep, but ugly goes to the bone” (Dorothy Parker). Epigram: A short, clever, usually barbed statement; a short poem about a single subject, often ending with an unexpected or clever twist of thought. A famous Dorothy Parker epigram about Oscar Wilde is, “If, with the literate, I am/Impelled to try an epigram,/I never seek to take the credit;/We all assume that Oscar said it.” Repartee: A quick, droll response or comeback; witty banter. For example, in response to a witty comment made by the painter James McNeill Whistler, Oscar Wilde once remarked, “I wish I’d said that”; Whistler replied, “You will, Oscar, you will.” Quip: A general word for any witty remark; see “witticism.”

Observe witty people. Think of people you know who are particularly witty, and try to dissect why. What characteristics do they have that you find interesting or amusing? Be as specific as possible; when you’re learning something new, the first step is to break it down into smaller chunks in order to understand and replicate it.

Be curious. Witty people are constantly asking questions and learning—if you accept everything at face value without engaging your curiosity, you won’t have much to quip about. As Dorothy Parker wrote, “Wit has truth in it; wise-cracking is simply calisthenics with words." To say interesting things, one must be both interested and interesting. Indulge your obsessions. Find something about which you are passionate, and dive into it. Learn as much as you can. The more you know about something, the better equipped you are to say clever things about it. Listen to and take genuine interest in the people around you. You’ve probably known someone who was so preoccupied with thinking of his next joke that he never seemed fully present in conversation. Did this person seem particularly witty? Probably not. Most funny people are keen observers of the world around them. The people you talk to are like partners in an improve scene—if you’re not paying genuine attention to them, you won’t be able to respond in an engaging way. Think critically and creatively. Aristotle called wit “educated insolence,” and if you consider people like Louis C.K., George Carlin, Sarah Silverman, and Richard Pryor, you may find yourself in agreement. These iconoclastic comedians use unexpected barbed critiques of the status quo as a vital part of their humor. Think of an injustice in the world that rankles you, and try to find an original way to frame the problem.

Immerse yourself in wit. Oscar Wilde once quipped, “Quotation is a serviceable substitute for wit.” Ideally, exposing yourself to a wide array of witty media will help you learn about wit through osmosis; failing that, though, you can always follow Wilde’s advice, and store up some witty quotations as a substitute. Read books. A lot of history’s best examples of wit come from literature. Good places to start include Dorothy Parker, Vladimir Nabokov, P.G. Wodehouse, William Shakespeare, Jane Austen, Kurt Vonnegut, James Joyce, Voltaire, Gertrude Stein, George Elliot, Mae West, and Oscar Wilde. Watch standup comedy. Comedians make a living off being witty, and lots can be learned from observing them. Some particularly witty comics include George Carlin, Lenny Bruce, Richard Pryor, Sarah Silverman, Jerry Seinfeld, Mitch Hedberg, Maria Bamford, Ellen Degeneres, and Greg Proops. Watch movies and television. There is much to be learned about wit from watching funny television shows and movies. Some great examples are Anchorman, The Princess Bride, Monty Python, 30 Rock, Frasier, The Office, The Colbert Report, The Daily Show, Last Week Tonight, Dr. Strangelove, Strangers with Candy, The Importance of Being Earnest, In The Loop, and anything by Woody Allen.

Expressing Your Wit

Have respect for others. Some people think wit means being mean and sarcastic. While it’s true that there are plenty of examples of witty remarks made at the expense of others, being witty doesn’t have to mean being cruel. That said, there is a time and a place for backhanded comments and cutting rejoinders. A good rule to follow if you’re going to take shots at other people is to take at least as many shots at yourself. Tempering sarcastic comments about others with self-deprecating jokes will make you seem more fair, and less like an insult-machine. After all, if you alienate people, there will be no one to appreciate your wit.

Present the appearance of confidence. Of course, genuine confidence is always preferable to feigned confidence, but there are plenty of witty people who are plagued by self-doubt. If you fade into the background, however, or seem not to believe in your own jokes, it will be hard for other people to relax and appreciate your wit. It is certainly possible to be off-puttingly over-confident as well, and there are a number of witty people (like Woody Allen, Mitch Hedberg, and David Sedaris) who cultivate a persona that takes advantage of their neuroses for comedic effect. Even these people, however, know how to present their jokes with enough confidence that their audience is not too worried for them to laugh, or made uncomfortable by their discomfort. If you are not a very confident person, don’t fear. There is a lot to be said for faking it till you make it; if you present the appearance of confidence, you may find yourself becoming more genuinely confident with time. Stand up straight, speak slowly and clearly, and smile. This can go a long way toward making people receptive of your jokes. Remember: if you want to feel confident, you have to try things! Sometimes you will be amazing right away, and sometimes you will fall flat on your face. Confidence revolves around the idea that you can get through anything, even if it's tough.

Be brief. Perhaps history’s most famous quote about wit comes from Shakespeare’s Hamlet: “Brevity is the soul of wit.” The contemporary writer George Saunders elaborated slightly on this theme when he wrote, “Humor is what happens when we’re told the truth quicker and more directly than we’re used to.” The best witty quips are short and pithy; don’t belabor the point. Your wit should be a pleasant addition to a conversation, not its primary focus.

Study vocabulary. A large part of being witty is the appearance of cleverness; improving your vocabulary can only help in this regard. There are a number of “word a day” style apps for your phone that can help with this. Alternatively, flip through a dictionary and make a list of words you would like to add to your active vocabulary (“active vocabulary” refers to words you use in your day-to-day speech, as opposed to “passive vocabulary,” which refers to words you recognize upon reading or hearing, but do not personally use) and make flashcards to quiz yourself.

Practicing Creative Thinking

Play lateral thinking games. Lateral thinking is the ability to solve problems by making connections between seemingly disparate things, and is essentially what fuels creativity. Not everyone is comfortable thinking laterally, but it is a skill that can be strengthened with practice. Grab a pen and paper, and think of five random, unrelated nouns. Spend 30 seconds or so generating a list of things you can do with each object. Be creative; don’t just list their most obvious uses. Now pick two of the items on your list, and use the list of uses for them you brainstormed as a jumping-off point to write an original joke. An example of a joke written this way by comedian Max Matterson is, “In what way are pencils and judges the same? They pass sentences, always have the last word, and are wright all the time.” Don’t worry if you struggle at first; with practice it will become easier. With a friend, brainstorm a list of random objects. Write each one down on a piece of paper, fold them up, and put them in a bowl. Draw a piece of paper at random, and set a timer for 1 minute. Come up with as many uses for that object as you can before the timer goes off. Read them aloud, crossing out the uses that the other person also listed. Whoever has the longest list at the end of this process wins. Think of a random word, and have a friend do the same. On the count of three, both of you say the word you are thinking of, at the same time. Count to three again, and this time both of you try to say a word that is somehow between the two words you said in the first round. Continue doing this, with the goal of eventually both saying the same word. This will strengthen your ability to draw connections between things that are not obviously related.

Do lateral thinking puzzles. These are designed to improve your ability to connect seemingly unconnected ideas, and will help you learn to be creative on the spot. Generally lateral thinking puzzles take place as a dialogue of yes-or-no questions between a quizzer and a solver, but you can try to puzzle these classics out on your own, and then follow the links provided to find the answers when you think you’ve got it. Take your time; these are designed to be ambiguous, and may take you a while to puzzle out. Try reading one in the morning, and then turning it over in your mind over the course of the day. If you come up with an answer that works but is different than the canonical answers provided, give yourself a pat on the back! You are definitely thinking creatively. (If you enjoy these puzzles, there are many more like them on the internet—just Google “lateral thinking puzzles.”) A man lives on the tenth floor of a building. Every day he takes the elevator down to the ground floor to go to work, or to go shopping. When he returns he takes the elevator to the seventh floor and walks up the stairs to reach his apartment on the tenth floor. He hates walking, so why does he do it? Click here for the solution. A man walks into a bar and asks the barman for a glass of water. The barman pulls out a gun and points it at the man. The man says “Thank you,” and walks out. Why? Click here for the solution. There is a large wooden barn that is completely empty except for a dead man hanging by his neck from the middle of the central rafter. The rope around his neck is ten feet long and his feet are three feet off the ground. The nearest wall is 20 feet away from the man. It is not possible to climb up the walls or along the rafters. The man hanged himself. How did he do it? Click here for the answer.

Play improv games. These are designed to force you to think on your feet without judging your ideas or getting in your own way. If you don’t have friends who are interested in playing improv games with you, check online if there are any improv classes in your area. Remember, the most important rule in improvisation is to say, “yes, and…” If your improv partner starts a scene in which she tries to return something to a store, don’t respond with, “What are you talking about? This isn’t a store!” It may seem like a funny response at first, but it will make your partner feel foolish, and leave you both with nowhere to go. Instead, accept her premise, and build on what she has established. Park bench: Begin with two chairs side-by-side. Start with one person sitting in one of the chairs. A second person enters, sits on the chair beside the first person, and begins a scene that takes place on a park bench. The goal of the second person is to scare away the person originally sitting on the bench. When he has done so, he moves into their seat, and another person enters and invents a new scene, with the goal of scaring off the person already on the park bench. Questions only: This is a very straightforward game, in which two participants act out a scene using only questions. When someone messes up and fails to speak in the form of a question, they are out, and another member of the group replaces them. Alphabet: Also very straightforward, this game involves two people acting out a scene in which the first word of every sentence begins with the next letter of the alphabet. So the first person might say, “A very fine day we’re having,” to which the second person might say, “Bit chilly for me.” The first person would respond with something like, “Can you go two minutes without complaining?” and the second might reply, “Don’t start with me.” When someone messes up or gets stumped, a new player replaces them, and the game starts over at “A.” Belief to Delusion: Start with an established fact, like “pizza tastes good,” or “dogs are cute,” and then act out a scene where this fact is no longer true. Boring: Start with a boring task, and play out a scene in which this task becomes the goal of an epic quest.

Pour yourself a drink: This is certainly not a requirement, and you don’t want it to become a crutch, but drinking a little alcohol can help you relax, making it easier to think creatively. According to Benjamin Errett, author of Elements of Wit: Mastering the Art of Being Interesting, having a couple drinks can help, so long as you don’t overdo it. “To a point I've done some science,” he says, “and decided that people are at their wittiest after two drinks. Any more and you lose perspective on yourself.”