How to keep a conversation alive (and actually interesting)


How to keep a conversation alive (and actually interesting)

A major fear that I usually faced was encountering the big awkward silence whenever I spoke to someone. It was like there was an imaginary creature in my head asking me how long I can keep the conversation going.

How to keep a conversation alive

The fear of the awkward silence is so vast in our society that it’s one of the main reasons people and introverts alike prefer staying to themselves. (Introverts love silence when they’re by themselves.)

I usually assumed the reason I often came across awkward silence was due to how boring I was. This led me to a few books that opened my eyes to understand my flaws and mistakes and what I learned changed my life. It wasn’t the fact that I was too boring to speak to, but because there’s actually an art to keeping a conversation alive and healthy.

How to Keep a conversation alive

I already went through in great length on the best ways I built my social skills and became a boss at making associates (or friends as some would prefer.) If you’d like to catch up on that, I recommend reading it Here. But to save you ten minutes of reading a simple point, speak to more people to open up more doors of opportunity.

But while it may be easy to simply walk up to strangers and introduce yourself, it brings up the next question of, “What next?” Once you reveal what happened in your day and heard their own story, it conjures up the biggest question. That question is: What should I say next?

Forcing a conversation does nothing more than make that awkward silence more bothersome once it approaches you again. But just standing in front of someone as if you’re in a staring contest isn’t going to help either. In the long run, whether you’re an introvert or extrovert, you want to learn how to keep a conversation alive. It overcomes your shyness and defeat those bothering barriers. (You might even make a new friend.)

This doesn’t mean keeping a pack of index cards with you that has conversation topics on them. In the next nine minutes, we’re going to hack your brain to ensure you keep a conversation going organically. And hey, if this doesn’t work for you, don’t think of it as the end of the world. I have several popular topics on the art of mastering your conversation skills that goes into great detail.

1. 12 Ways to Become a Skilled Conversationalist

2. The 10 Laws that Conversationalists use to Win People Over

Anyway, I hate beating a dead horse with a stick (I think that’s how the phrase goes. Correct me if I’m wrong.) Let’s get straight to the point and rewire your brain. Here are the 3 major points that can help you keep a conversation alive and somewhat entertaining.

1. Pretend to be a Detective

how to keep a conversation alive

To get the conversation started, ask questions. Dig into their life. Even if you’re not interested in Billy’s baseball card collection, ask questions to dig deeper into that subject. Most of the time you have conversations with people, you’re not doing it to discover Samantha’s love for Britney Spears. You’re doing it to gain that human interaction feeling that feeds into your brain.

Ask open-ended questions that forces someone to answer you with more than just a one word response. Examples would be, “Why are you into baseball cards?” “Why do you like Britney Spears?” “When did you start listening to Britney Spears?” “When did you start collecting Baseball cards?’

Get it? Do you want to dig even deeper into this subject? We’re going to play a game called, Detective. Imagine yourself to be your own version of Sherlock and your goal is to deduce someone’s life. Whoever the person you speak to, you must define and break down their general interests to the smallest details. Learn when they started doing something, why they started doing something, and ways it impacted their life.

Humans are creatures that enjoy speaking about themselves once they’re given the opportunity. Before turning to those big questions such as, “How was your weekend” let yourself inquire the elementary problems such as, “What was the story of your weekend?”

Once they do provide you with a response, break their answer into bits and dig deeper into any of those areas. For example, suppose Ashley responded to me with, “It was okay. I went to the Zoo and bought some clothes.

I can nod my head to Ashley and tell her I don’t care. But that’s not going to help anyone. Instead, I have the opportunity to dig deeper into either her time at the Zoo, what made her go there, what animals stood out to her, or my own personal experiences at the Zoo.

If I wanted to dig into her adventure in buying clothes, I would ask her what she got, what store she shopped at, or the reason she bought those clothing.

Don’t be afraid of drowning someone with questions because in most conversations where you ask questions, the other person tends to do the same. They naturally pick up what you’re doing because it’s working and keeping the conversation alive.

Even if you have to pretend, act genuinely interested in what they have to say so they’ll talk even more. You don’t have to be a conversationalist genius so long as you know how to ask the right questions and provide the right responses and expressions.

2. Don’t Limit Your Topic of Interest

how to keep a conversation alive

Never get it twisted in your mind that you must watch out for everything you say. Oftentimes, people are more focused on what they should and shouldn’t say in a conversation to keep a good appearance. I know this because I constantly did this too. When I spoke to anyone, all I thought about was, “What can I say to look cool?” “Will she like me if I say this or that?” “What can I say to make her like me?”

The “can I say this” game is too troubling to deal with and it happens to more people than you think. It’s probably occurring in the person’s head you’re speaking to also. So save you both the trouble by not being afraid to actually say what’s in your mind.

This doesn’t mean spitting out crazy things that will get you hurt or exiled from society. Tell someone your honest opinion about what you think about a party, what they’re wearing, or if you really like Game of Thrones.

But I’m nice. (Or at least I like to think I am.) So I’m going to break down some hard case examples on how I ignore my fear of saying the wrong thing.

Whenever I approach someone, whether it’s a stranger, associate, or friend, I normally start off with a proper greeting. From there, I like to describe a recent experience I went through that was stranger than usual. For example, I can tell Ashley about a restaurant I ate at that I haven’t been to for years. (It was Burger King for those wondering.)

Now Ashley does have the right to only nod her head and not contribute anything to the conversation. But there’s a little thing known as Common Sense that tells people to say something in relation to my recent event at Burger King. She could tell me she like it, never heard of it, or they hate it. In this case, she mentioned she enjoyed it and haven’t been there in a while either.

Rather than changing subjects, I stick to the topic of Burger King and tell her about a new food item known as the Chicken Fries. I have no interest in knowing if she enjoy eating Chicken Fries or not, but I want to see where this conversation will lead us.

That’s when she told me she never had it before and as a response, I give a shock reaction. This adds emotion into the conversation and I then ask her what restaurants she enjoy eating at if she doesn’t eat at Burger King that often. This turns the conversation to either the restaurants she like and my own opinions about them. Or it can take us to her love for cooking and digging deeper into those subjects.

The solid point is this: Don’t sweat about what topic you bring to someone. Only focus on ways you can dig deeper into it. There’s no reason telling someone you like Burger King if that’s the only time you plan to mention it. This is how conversations turn into a game of hot potato of just passing useless facts to each other with no purpose other than filling the air with noise.


3. Be Witty and Funny When Possible

how to keep a conversation alive

Who doesn’t like a comedian? You’d be surprised how often a comedian is invited to a celebrity’s home because they’re pleasant to be around. They release other people stress and help them temporarily forget life worries.

Being witty isn’t a skill that’s easily acquired because it requires being spontaneous and clever on the spot. You have to combine being aggressively bold and humorous elements into one mixture that relates to a current event. Say the wrong thing and you can turn an entire crowd against you. But say the right thing and you’ll make them addicted to you.

Examples of witty comments are:

“Give a man a match, and he’ll be warm for a minute, but set him on fire, and he’ll be warm for the rest of his life.”

“Expecting the world to treat you fairly because you are good is like expecting the bull not to charge because you are a vegetarian.”

“Advice for the day: If you have a headache, do what it says on the aspirin bottle: Take two, and KEEP AWAY FROM CHILDREN.”

“Never interrupt your opponent while he’s making a mistake.”

“Friendships last when each friend thinks he has a slight superiority over the other.”

“I love deadlines. I especially like the whooshing sound they make as they go flying by.”

“If you don’t like the way I drive, stay off the sidewalk.”

“Basic Definitions of Science: If it’s green or wiggles, it’s biology. If it stinks, it’s chemistry. If it doesn’t work, it’s physics.”

“I talk to myself because I like dealing with a better class of people.”

Do you have a general understanding how being witty works? What you want to do is take a serious topic and twist it towards a funny perspective. Those who take life too seriously are rarely worth following because we all deal with that sort of environment everyday. That’s why when they find someone who knows how to turn a serious topic into something amusing, they instantly fall in love with them. (Not romantically, of course.)

Other methods to mastering your own form of wittiness is pushing off one of your own personal stories and turning it into a joke. Avoid complaining about something bad happening to you and turn it into a humorous tale.

Last week I was stung by a bee and that was freaking painful. My index finger looks like it forgot to follow the Jenny Craig diet and I couldn’t even bend it. But I didn’t complain about it to my friends. Instead, I told them about my experience and the awkwardness I dealt with while trying to determine if was I allergic and do any bees contain poison. (Yep…getting stung by a bee mentally scarred me.)

Of course you’re going to need practice before you get this skilled under your control. I recommend making witty comments to yourself when you’re alone. Make a joke out of what could have been an irritating situation (such as waiting in a long line at Wal-Mart.) Learn to laugh at yourself and make a punch line out of your bad experiences.

In final thoughts…

Hope you had a great time having your brain rewired. Have any personal tips or strategies you use to keep your conversation alive? Feel free to share them by either comment or with other users in the Chat Room.

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Like this article, check out

12 ways to become a skilled conversationalist

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How To Easily Keep a Conversation Going As an Introvert


About Author

Besides being random and dealing with ADHD from time to time, Michael Gregory II is the CEO of the Self Development Workshop. He's traveled to over a dozen countries, counselled a variety of people, and continues furthering his knowledge in self-development, depression, and mastering your happiness. On his lazy days, he enjoy watching people, reading in Starbucks, and speaking to random strangers. (Yeah, he’s weird.)

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