How to Improve 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.^[16] 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.^[17]
• Confidence revolves around the idea that you can get through anything, even if it's tough.^[18]

Be brief. Perhaps history’s most famous quote about wit comes from Shakespeare’s Hamlet: “Brevity is the soul of wit.”^[19] 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.^[20] 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.

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.