How to Have a Witty Conversation
Being witty in conversation may seem hard, but by relaxing and practicing some basics, you'll find it easier. Start conversations at social events with small talk whenever you get the chance, since you can't be witty if you don't engage with other people. Try to introduce funny anecdotes into your conversation, like a humorous experience you had that fits with the other person's interests. You can also try to work in wordplay, like puns and portmanteaus. For example, “She had a photographic memory but never developed it” is a pun, whereas “Chrismukkah,” a combination of Christmas and Hanukkah, is a portmanteau. Try to relax during your conversations, since you'll seem wittier if you're enjoying yourself. Remember to pay attention to others when they speak rather than focusing on your next witty comment. This is important because your witticism will probably fall flat if it's not related to the conversation.
Put good conversation before witty conversation. Before you can be witty, you need to improve your "conversational intelligence." No matter how witty you are, launching into a conversation with a humorous story or a joke can come across as overbearing. Practice the "Observe-Ask-Reveal" method of being a conversationalist. Begin by making it clear that you're interested in conversation. In social situations, its important to look approachable by giving nonverbal cues, such as adopting open body language and smiling. Get a conversation going by engaging in strategic small talk. Every conversation needs to start somewhere. Begin with innocuous questions or comments about things around you to get a conversation going. Are you outside? What's the weather like? Are you at a party? What kind of food is being served? If you're speaking to a stranger, pivot from small talk to personal introductions and let the conversation develop from there. Ask questions. In order to know what the person you're talking to will find amusing, you need to know more about them. Most people are happy to talk about themselves, provided you give them the opportunity. Avoid "yes" or "no" questions. Instead, keep them open-ended. For example, when someone tells you their occupation, ask their favorite part of their job. When in doubt, ask "Why?" Let your conversation partner know you're genuinely interested in what they have to say by maintaining eye contact and subtle interjections like "Really?" "Yeah?" and "Uh huh." Avoid interrupting your conversation partner, even if you think of something to say. Pay attention. Too often, if you're trying too hard to be witty, you'll neglect to listen, because you're trying to think of your next comment. In order to be witty, though, you need to pay close attention to what your conversation partner is saying. Listen attentively to your conversation partner's words. Don't interrupt. Even if something your conversation partner says sparks an idea for a comment, don't speak until there's a natural break in the conversation. Even the best comments, if made in the form of an interruption, can come across as rude. Note the rhythm of the conversation. Witty banter depends on timing. Listen closely to understand your conversation partner's speech patterns so that you'll know when to jump in with a comment. If you miss the moment, an otherwise witty rejoinder will fall flat. Look for commonalities. Once you know more about your conversation partner, you can begin to decide what you have in common and what might be the best mutual topic of conversation. Think of amusing experiences you've had that relate to your conversation partner's interests. At the appropriate time, bring your experiences into the conversation. Sometimes, all it takes is one experience. For example, if the person you're talking to enjoys fishing but you've only been fishing once, think about what novice mistakes you made that your conversation partner might find amusing. Know your audience. British author Somerset Maugham once said “quotation…is a serviceable substitute for wit.” Indeed, cultural references — from books, songs, films, television, politics, etc. — can provide a shortcut to wit. However, in order to ensure your references don't fall flat, you need to know your audience. For example, if you're talking to a Baby Boomer, inserting a Beatles lyric into the conversation likely will be more effective than referencing a Taylor Swift song. Get anecdotal. Everyone enjoys a funny story. But it's hard to elicit laughs from a meandering or vague anecdote. Instead, you should strive to have several crisp, well-worded stories ready to tell at parties and other social events. Think of the most amusing or odd stories from your life. These should be your go-to stories in conversations. Consider the likely audience for your anecdotes. If your goal is to see witty in conversations at an accounting convention, stories related to accounting might be appropriate. However, if you're looking for witty stories you can tell anywhere, using common experiences such as school or parents or pets or children are best, since more people will be able to relate to them. Make it funny. The same basic story can either be confusing, boring, or gut-busting. In order to make sure your story brings the laughs, you'll need to polish it. To get an idea of what makes a story funny, study the humorous phrasing and selective exaggeration employed by autobiographical humorists like David Sedaris. Begin outlining your story. Try to remember details. Revise your anecdote crisp, clear, and humorous. Then work on memorizing and fine-tuning your verbal delivery so that it comes across as funny in person as it does on the page. Have good banter. If other people join the conversation, feel free to make fun of them. Make fun of celebrities, singers or politicians. Just make sure that the other person is not a great fan of the celebrity your choosing to pick on. Don't go over the top. Don't make fun of someone's appearance, family situations, sexuality or disabilities (if any) unless you know it is something they are quite open about. Even then, even though they make self-deprecating jokes, they might not want to hear it from other people. Play with words. Few things come across as wittier in a conversation than clever wordplay. Even if wordplay doesn't come naturally to you, you can improve with practice. Know your vocabulary. Most wordplay depends on having a wide vocabulary. Consider vocabulary-building books, smartphone apps, and games, like crossword puzzles, to improve your command of words. Know the types of wordplay. Spoonerisms (“It's roaring with pain” instead of “It's pouring with rain”), malapropisms (“dance a flamingo” instead of “dance a flamenco”), puns (“She had a photographic memory but never developed it”), and portmanteaus (“Chrismukkah,” a combination of “Christmas” and “Hanukkah”) can all be wittily inserted into conversation if used well. Study examples of good wordplay. Everyone from Shakespeare to George Carlin to Kanye West employs wordplay in their writing and performances. Keeping your audience in mind, consume examples of good wordplay to help you understand how to employ it yourself. Relax and be yourself. People often want to be witty because they think they aren't good conversationalists. But insecurity is the enemy of wit. Good delivery often is the difference between a comment eliciting a laugh and falling flat. If you seem nervous or timid, your witty comment will not come across as well. It's important to remember that your perception of yourself is often inaccurate. You're probably not as awkward as you imagine, and by letting yourself feel insecure, you're actually hampering your ability to be witty. Build your confidence with practice. Paradoxically, the only way to overcome insecurity in conversation is to have more conversations! The key is engaging in low-stakes interactions (banter with a barista while you're waiting for your latte) as often as possible so that in high-stakes conversations (talking with the coworker you'd like to ask out) you're able to be witty. If necessary, (temporarily) retreat to the web. If face-to-face interactions make you nervous, try practicing your stories, puns, and other newly developed wit skills on social networking websites. Giving yourself a chance to work on your wit when you have more time to think might help you build your confidence so that you can be more relaxed during in-person interactions. Quit while you’re ahead. As you become more confident, you'll not only be able to move on when an attempt at wit falls flat, you'll also know when to stop trying to be witty. Shakespeare said “Brevity is the soul of wit.” Once you believe you're witty, you won't feel the need to try to make every comment witty — an effort that is bound to annoy or bore your conversation partner. Likewise, as you gain more confidence in your wit, you'll learn when to quit. It's always best to end a conversation on a high note. 
Put good conversation before witty conversation. Ask questions. Pay attention. Look for commonalities. Get anecdotal. Make it funny. Have good banter. Play with words. Relax and be yourself. Build your confidence with practice. If necessary, (temporarily) retreat to the web. Quit while you’re ahead. 