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How to have a witty conversation
Being witty is a good way to use your intelligence and knowledge to amuse people and enliven conversations. It can also be an impressive flirting tool! Everyone loves being around a person who has their wits about them, and it's especially effective if you're witty enough to make others feel witty as well! We'll show you a few ways to do that.
Steps
1: Listen well. Start by paying attention to what somebody is saying to you, and reflect it back to them in your own words. It shows that you've not only processed their ideas, it shows you actually considered them.
In being witty, however, you're going to reflect their words in a different way—strike a comparison to something else, ideally something that you and your conversation partner are both familiar with.
You'll be implying that you understand them by comparing their statement to something else. The more well-read, the more of that "something else" that you know, the more comparisons you can make, and the wittier you can be.
2: Use creative and vivid exaggeration. This has a way of not only providing a platform for your wit, it can also frame a discussion.
Let's say your friend is telling you how cross-eyed his teacher is. You can say, in response, "She's so cross-eyed that when she cries, the tears run down her back!"
3: Use puns. Take a word or phrase that the other person just used, and use it in a different way that still ties into the conversation.
Let's take the example from the previous step: "...the tears run down her back." If you're feeling witty, and there happen to be a stethoscope laying around, because you always carry around a stethoscope with you, hold it up mimicking a doctor and say "Evidently a case of bacteria!"
If you have to say "get it... back-tear-ia?" then you need to work on your delivery.
Wittiness means keeping the context clear. If there wasn't any medical context to the conversation, that response would be totally random, and not very witty.
You can also use a word in a sentence in a way that more than one of its meanings are relevant.
Read Shakespeare & Oscar Wilde. Their use of puns in dialogues are highly regarded.
Study the characters of the television show "M*A*S*H". An average episode can provide several examples of witty puns, as well as some of the pitfalls in overusing them.
Other masters come from satirical programs like Mock the Week. In particular, look for Frankie Boyle, Hugh Denis, and Dara O'Briain.
4: Use metaphors. Let's say someone says, out of the blue, "It's 6 o'clock!" You can say "Thank you, Big Ben!" ("Big Ben" is a nickname for a giant bell in a clock in London.) This is a particularly sarcastic example, because you're also implying (by saying "thank you") that you're obviously not thankful!
Not all metaphors have to be sarcastic. Describing your son's messy room, for instance, as the site of Hurricane Bob, is a witty and creative way to say it's quite messy, and Bob's responsible. You can also use witty metaphors to compliment or admire someone.
See How to Write a Metaphor for more insights.
5: Respond with a relevant quotation from a movie, book, or significant figure. The more obscure the reference, the wittier the statement—but the greater the confusion if the person you're talking to doesn't know what you're referring to.
If someone says "I'll try" and you say "Do or do not; there is no try," they may, or may not, realize that you're making a Star Wars reference. If they wittily respond with "The force is strong in you," you'll know they got it.
6: Reply quickly and nonchalantly.The wittiness is not only in how creatively you can link ideas and draw comparisons, but also in how quickly. And keeping your witty remarks in a casual tone makes it look like it was so easy. A playful smile and a raised eyebrow can also add a nice touch!
7:Think about everything before it happens! If you already have a response to something before it happens then when (and if) it happens it will seem like it was easier for you to think of a response. Just make sure that you pay attention to what actually happened and if your response makes sense before you say or do it.
Warnings!
Use your wittiness sparingly. If suddenly everyone hears the same references over and over again, they will start to doubt your wittiness and intelligence, and may just think you're a jerk.
Some aggressively witty individuals may take your use of wit in a conversation as an invitation to engage in a battle of wits. While this can be an enjoyable and engaging activity, it also has the potential to seem personal. Be prepared to set your limits and respect the limits of others to avoid hurt feelings.
There is such a thing as being too witty—there is indeed a fine balance between making witty conversation and just showing off and alienating the person (or people) you're talking to.
Using your wittiness to put people down without them realizing is low. It's moralistically "low" and also figuratively "low" because you put someone down.
If the person you're having a conversation with isn't grasping your wittiness, you might come off as a snob, or just plain weird. In that sense, it's a good way to see if you've met your intellectual match.
Be aware of the other person's feelings or emotions when saying something witty.