How to Not Be Boring in Conversation

12 min readMar 18, 2021

Conversations aren’t boring if the people in them are not.

While you don’t need to be a master conversationalist or a comedian to be socially entertaining, being boring, bland, and not taking (some) social risks could see your conversations ending prematurely while the other person finds the quickest way out.

Here are a few changes you can make to stop being boring in conversation.

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The “Yes And…” Mentality

The “yes and… “ mentality means that you take their conversational thread and add something to it.

Think of it like playing tennis. For a tennis game to be fun, you need both players to keep hitting the ball back and forth. One person serves (starts a conversational topic) and the other hits the ball back (good reply) and they go back and forth building on each person’s reply.

If you take a look at any good, free-flowing conversation, both people are following this exact principle whether they know it or not.

Example of a “yes and…” conversation about sports:

A: Do you watch any sports?
B: Yeah I watch basketball.
A: Man did you see Kawhi’s game-winner against the Sixers?
B: That was awesome! They’re going all the way this year.
Conversation continues…

Notice how each person added to what the other person said? This would naturally continue until someone brings up another topic of conversation and they go again from there.

Of course in this example, the person had knowledge of the topic of conversation, basketball, but the same principle holds true even if one isn’t too knowledgeable about the topic.

Example of a “yes and…” conversation about sports but one person isn’t as knowledgeable:

A: Do you watch any sports?
B: I watch sports here and there but don’t really follow?
A: You should’ve seen it yesterday. Kawhi Leonard from the Toronto Raptors hit a game-winner against the Sixers in the last game of the playoff series. The ball was bouncing around the rim and finally went in and the crowd went crazy.
B: I wish I saw that. What happens now?
A: Now the Raptors play the Milwaukee Bucks.
B: Who do you think wins that?
Conversation continues…

The opposite of a “yes and…” conversation is when someone gives an answer that doesn’t add on to anything the other person mentioned and the burden of restarting the conversation goes back to the person who started the topic initially.

Once again, if you think of it as a tennis game, a fun, free-flowing conversation is a game where both people are hitting the ball back and forth after one person serves but a conversation where someone gives a boring, flat answer is like serving the ball… and no one’s there, so you have to run over to the other side of the court, pick up your ball, run back to your side, and serve again. That is a very lonely game that the person will leave sooner rather than later.

Example of a conversation that the other person doesn’t add to:

A: Do you watch any sports?
B: Not really.
A: What do you usually watch?
B: I don’t usually watch anything.

Reading this, you might be laughing at that example. But this type of conversation is extremely common. If it wasn’t such a big problem, I wouldn’t be writing this but I am because it is.

Be Knowledgeable

Conversations using the second example of the “yes and…” mentality is good for when you don’t know what the topic of conversation is about but if most of the conversation with the other person is like that, it will also become a boring conversation since it will seem like a one-sided explanation of various topics.

Most people like explaining and teaching things to people but not for the majority of the conversation or friendship.

Going back to our tennis analogy, a conversation where one person is knowledgeable and the other is not is like Roger Federer playing against an infant. Roger is going to blast 117mph serves and the infant isn’t going to hit any balls back so there is virtually no chance of fun back and forth.

Being knowledgeable doesn’t require you to be a walking-talking Google or have 5 doctorate degrees, but it means you know enough about what you’re talking about.

Ideally, you should have several topics you know inside out and then know about a wide range of topics.

The range of being knowledgeable include:

Being an expert on the topic: knowing the topic inside and out, you can explain virtually anything to anyone.
Being educated on the topic: knowing enough about the conversation to offer interesting perspectives and share information.
Being conversational about the topic: knowing enough about the topic to hold your own in a conversation.
Being ignorant about the topic: not knowing about the topic.

Common topics of conversation that it helps to be knowledgeable about can include:

Hockey
Basketball
American football
Baseball
Football (soccer)
Boxing/ mixed martial arts
Politics
World events
Movies and television shows
Video games
Books
Podcasts
Business
Career
Finance
Health and fitness
Music
The city/ town you live in
Food
Alcohol
Celebrities
Travel
Children
Restaurants
Cars
Coffee/tea
Cooking
Clothes
Shopping
Goals and habits
Social media
Self-improvement
Languages
Animals
History
Psychology
Law
Science
Religion
Dating/ sex

Be Funny

People connect very strongly over shared laughter. Think about all the best moments you’ve had with your friends, many of those moments involved you two laughing and enjoying yourselves right?

Humor is a way for us to laugh, enjoy ourselves, and connect, but it’s not that complicated. You don’t need to be a Dave Chappelle or a Kevin Hart who makes stadiums full of people laugh with every other sentence, a few funny moments throughout an interaction is all you need to be funny.

Rules of Humor

Humor, like anything else, is not by accident. There are certain rules that make humor funny.

Commit to the Humor

Something that makes people extremely funny without any knowledge of their jokes or the content of their words is their commitment to humor.

If you watch any good standup comedian, you’ll notice that when they’re telling a story or telling a joke, they are fully committed to the delivery. Everything from their vocal tonality, facial expression, to their body language is part of the joke.

What do people who aren’t funny do? They say their joke half-heartedly (or don’t even say it at all) which results in them not being funny. The difference between them and the Dave Chappelles of the world (aside from their talent), is vulnerability.

Comedians are being extremely socially vulnerable when they’re on stage. They are fully committed to telling a joke which if it falls flat and the audience doesn’t laugh, they can look like a complete fool on stage. They are willing to do this because they know that the full commitment to their joke is what makes the joke funny in the first place. People who aren’t funny hedge their bets by being duller and less enthusiastic, which unfortunately makes them less funny, if at all.

Being committed to your humor doesn’t necessarily mean you’re crazy, loud, and over the top, but it just means that you are telling the joke without hesitation, also known as being socially vulnerable. Kevin Hart is super crazy and over the top when he is committing to a joke or a skit, but Dave Chappelle is often pretty calm and relaxed, both are extremely funny people.

Don’t Overdo Humor

Overdoing humor can be just as annoying as not being humorous at all. Unless you can be funny without putting much effort into it or your personality is funny, don’t seek to overdo the humor.

Being constantly funny works great if the majority of the things you say are funny, which come with experience, talent, and a certain personality, but if you’re working on becoming funny, just worry about being funny a few times as opposed to trying to do a 1 hour Netflix comedy special.

Make Yourself Laugh

This can be referred to as self-amusement, but this is when you focus on making yourself laugh which invites the other person to laugh too. This reduces your need to be socially vulnerable although still is, because you’re not depending on the other person to make your joke succeed. You simply tell a story or joke which makes you laugh and enjoy yourself, then the other person can join in on your laughter if they find it funny too.

Make Them Feel Included

People love humor when they feel like they’re in on the joke, not when they’re the butt of the joke. You can be funny and be a complete asshole, or you can be funny and supercharge your connection.

The difference is who is at the butt of the joke. If either no one or you yourself are the joke, then it’s funny and inclusive since you two are laughing together, but if they are the victim of the joke, it becomes threatening and standoffish.

Jokes and stories which don’t have to do with the other person should be fine for the most part, but if you are going to joke about the other person, keep the humor either neutral or build them up, just don’t push them down.

If someone has messy hair today, you can joke that the hair makes them look more badass if they put on a really nice suit and pretend to be the boss anytime they enter somewhere (builds them up). Or you can say something like: they’re looking closer and closer to being the Joker with every passing day (neutral, depending on how it’s delivered). But if you say something like: it looks like someone shaved your hair and put a dead raccoon on your head, this is obviously quite insulting.

This is why self-depreciation is so effective, because it makes the joke teller the victim of the joke and the other people can laugh with you while you laugh at yourself. If the joke teller had messy hair, then saying something like: it looks like someone shaved your hair and put a dead raccoon on your head, could be pretty funny.

Self-deprecating humor works really well if the joke teller is someone who is confident and/or high status since the joke brings them down a notch and makes them feel more relatable, but if the person is already quite depressive, unconfident, or makes too many self-deprecating jokes, it can just be sad. Self-deprecating humor follows the other rule of humor, don’t overdo it.

If you do end up making a joke that does seek to put someone down, also known as a diss, roast, or tease, make sure to go about it in a socially intelligent way. This means be careful of what you joke about. Make sure you’re not laughing at the expense of their insecurities. Nothing will kill a potential friendship faster than their insecurity being laughed at, whether the person making the joke did it intentionally or not.

How to Be Funny

There could be an entire book or course created on how to be funny but we’ll outline three common humor tactics used by everyone from your funny uncle, famous comedians, to people like you and me.

Saying the Unexpected

When we’re being told a story or a joke, our brains naturally try and anticipate what is about to be said next, but saying the unexpected breaks that pattern which shocks our brains and makes us laugh as a result.

To illustrate the point about anticipation, pretend you’re in this conversation:

You: Hey Mark how’s it going?
Mark: I’m doing well, what’s up with you?
You: Just reading this great book on leading a social life. Did you catch that basketball game last night?
Mark: Yeah! That game-winning dunk was crazy.
You: I can’t believe how tall people in the NBA are.
Mark: Yeah, I heard some people breed with giraffes in an attempt to make their kids taller.

Wasn’t that funny? When you said “I can’t believe how tall people in the NBA are”, you were expecting Mark to respond with something along the lines of tall people in the NBA, but nope… he was talking about human baby giraffes. Obviously, Mark isn’t being serious but his saying the unexpected would’ve made anyone laugh.

For another example of saying the unexpected delivered by a person far funnier than me, let’s turn to Dave Chappelle from his Netflix comedy special Sticks and Stones. (Transcribing comedy makes comedy sound way less funny since you can’t capture their tone or expressions well.)

Dave Chappelle speaks about the poverty mindset:

*David acting like his dad*: Just don’t think about how cold you are David.
David: And I said this. I didn’t say it to him but I said it in front of him so he could hear.
I said, “I HATE BEING POOR!”
And my dad got really upset. He didn’t scream or holler, that wasn’t his way. He just threw his newspaper on the floor and said: “David David David, you are not poor”
He said “poor is a mentality”
He said “it’s a mentality that few people ever recover from. Don’t you forget it son”
…
“You… are broke”

Exaggeration

Exaggeration is when you take something either normal or slightly funny and blow everything out of proportion. The joke is in the exaggeration of the original topic. This is funny because it also is unexpected but also because exaggeration makes things sound ridiculous.

Examples of exaggeration could be:

My coffee doesn’t taste very good today.

Yeah, I don’t think the slaves who were used to harvesting the beans cared if it tasted good or not. (Dark humor, but still funny)

The Seahawks are going to the Super Bowl this year!

Yeah, I think they’ll win more than one game! (Understatements are a form of exaggeration.)

I died laughing at that movie.

Same! My mom was about to call the coffin store telling them they were about to get a new customer.

Playing a Character

This one is my favorite to do. Playing a character is either when you imitate somebody or something to make an example, to exaggerate something the other person said, or even to say the unexpected.

The key to playing a character is to make your vocal tonality different when you play the character so the other person knows that you’re switching roles. If you’re going to play a character well, make sure you commit fully to playing the character. If you’re going to imitate a movie character, for example, commit fully. You don’t want a half character, half-real person. This ruins the whole point of being a character.

It would be extremely difficult to write out playing a different character but watch pretty much any comedian since they play different characters many times during their shows. Notice their commitment to the character.

Not Just Questions

If you keep bombarding the other person with questions, it may start feeling like a corporate job interview more than a fun conversation.

Mix it up by making statements instead of constant questioning. Statements give the other person an opportunity to add into the conversation at their own will which could lead to them investing more in the conversation and/or bringing up some new perspectives.

Examples of turning questions into statements can include:

Instead of asking them what they’re going to do this weekend, share what you will do.
Instead of asking them what they do for work, share something cool that you do.
Instead of asking them a question to get over an awkward silence, make a comment on something.

Storytelling

One alternative to talking in questions and statements is to tell a story. Humans are designed to be fascinated by stories, connect over-sharing stories, and learn very well through stories.

You may or may not remember facts, but you certainly will understand them if it’s told in an interesting story to go along with it. This is also the reason why you love to read stories, watch movies and TV shows, and play video games because they all are variations of stories. Everything from Thomas the Tank Engine to Assassin’s Creed video games are stories.

Pretty much all stories share the same general pattern. Stories can be of varying lengths and what you include in each part is up to you but they’re all similar in this sense:

Introduction: Introduce the people involved and the context.
Build up: build up the details and tell the story leading up to the main point.
Climax: this is the main point of the story. The big, dramatic moment of the story or the main idea you want to get across.
Alternatively, the anti-climax. An anti-climax is when the listener has been built up and is expecting a big climax but instead the climax turns out to be something insignificant and/or unexpected, which can also make for a great story.
Wind down: this doesn’t happen for all stories but after the climax, you can start to close the open gaps and prepare the listeners for the conclusion.
Alternatively, repeat the build-up. Some stories don’t just have one main point. If there are multiple, they can repeat the build-up after the first climax.
Conclusion: this is where you let the listener know the story is over.