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. [2] X Research source 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. [3] X Research source
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. “[4] X Research source Avoid interrupting your conversation partner, even if you think of something to say.
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.
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. [7] X Research source 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. ”[8] X Research source 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.
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.
To get an idea of what makes a story funny, study the humorous phrasing and selective exaggeration employed by autobiographical humorists like David Sedaris. [9] X Research source 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.
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.
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. [10] X Research source 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. [11] X Research source [12] X Research source [13] X Research source 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.
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. [14] X Research source 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. [15] X Research source
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.
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.
Shakespeare said “Brevity is the soul of wit. ”[16] X Research source 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.
