How to Keep a Conversation Interesting

  • Post last modified:April 27, 2020
  • Post category:Self Improvement
a boy and a girl sitting down writing in a notepad; the girl is laughing really hard

Imagine having the most interesting conversation of your life.

How does that look like? You’re laughing hard, giggling uncontrollably, completely engrossed in the conversation, constantly smiling.

We all have conversations we wish could just be a tad more interesting. Maybe you’ve met someone you like and you’re wondering how to strike an interesting conversation. Maybe you want to improve on the quality of your conversations. 

Most at times after the initial “hello, how are you doing” our conversations come to a screeching end; you just don’t know what to say after the initial greeting. Now you are bugged with the question “how do you keep your conversations interesting or entertaining?”. The answer is a simple one: by arming yourself with interesting questions that evoke interesting answers. 

Personally, there have been many times when my conversations have ended because we run out of things to talk about. Thus, learning to keep a conversation interesting has been both a great tool and a relief for me in my relationships. 

Learning to keep a conversation interesting becomes even more important when it’s someone you’d like to get to know better. The ultimate way to have the best conversation is to ask interesting questions while being genuinely interested in the answers; it works extremely well with people you like since you are most definitely interested in whatever the person has to say. 

Having interesting conversations will light up your life and keep things exciting; it will also make sure people remember you fondly. The following are questions that you should always have at the back of your mind or tucked away somewhere, so you can easily access them whenever you want to take your conversations to the next level. 

Questions To Keep a Conversation Interesting

  • What would you do if you won a million dollars?

This question stimulates the best conversations; it employs an important factor that motivates most people: money. I have used this question on several occasions and the answers I get are always interesting. I also get to ask follow-up questions that keep the conversation going. Whenever I’m stumped for conversation fodder, this question is my go-to question. 

  • Tell me something most people would never guess about you.

This question always brings up interesting answers that you’d never expect. It also allows you to get to know another side of the person you conversing with. 

  • Tell me about a movie/book you’ve seen or read more than once.

We all have a favorite movie or book we could talk about hours on end. This question draws your conversation partner strongly into the conversation.

  • What’s the best surprise you’ve ever received?

Good surprises always engender positive feelings. Inviting the other person to talk about these good surprises keeps the conversation interesting and on a positive note.

  • What’s your favorite thing to do?

This helps you get to know the other person better; their hobbies, likes and stuff they are passionate about. 

  • What are the top places you want to visit?

Every loves to talk about their dream vacation destinations. Use this question to start lively conversation.

Other Interesting Questions

  • What’s the neatest surprise you’ve ever planned and pulled off for someone else?
  • Who is the most famous person you’ve met?
  • What’s the most memorable meal you’ve eaten?
  • What’s the most unforgettable coincidence you’ve experienced or heard about?
  • What’s your favorite thing to do alone?
  • If the world was ending, who or which people would you wish to be around you? Why?
  • What would you like to come back as in your next life?
  • If you could replay any moment in your life, what would it be?
  • If you had three wishes, what would they be?
  • What/Who makes you happy?

Interesting Books To Read To Stimulate The Best Conversations

Books are the best sources of interesting knowledge; however, the average person reads just about 4 books per year. If you want to greatly improve conversation skills, reading interesting books is a surefire way to do that. Some of these books defy conventional wisdom and give you a fresh—sometimes controversial—perspective of the world we live in. Here are my top five interesting books to read:

  1. Captivate

The Science of Succeeding With People

By Vanessa Van Edwards

This is excellent book for anyone who wants to improve their social skills; I can’t recommend it enough. It offers fresh ideas and hacks that will help you level up your career, improve your relationships and increase your income. This book is a must-have for everyone ready to take his social life to the next level.

2. Your Pinkie Is More Powerful Than Your Thumb 

And 333 Other Surprising Facts That Will Make You Wealthier, Healthier and Smarter Than Everyone Else 

By Mark Di Vincenzo

An incredible book, full of bizarre facts that will leave you awe-inspired. The facts in this book are educative in a fun way; you will find yourself absorbed in the book, constantly anxious to discover the next exciting fact. You can share these fun tidbits with friends and family, leaving them gasping with ‘oohs’ and ‘aah’s’. 

3. 1000 Places To See Before You Die

By Patricia Schultz

So many people dream of traveling to exotic places all the time; engaging someone in a conversation about travels always engenders a lively and animated chatter. 1000 places to see before you die is filled with enormous information about so many wonderful places around the world that you’re bound to be overwhelmed by the sheer amount of information offered. Whenever you’re stumped for a travel destination idea, you could skim through the book for literally 1000 ideas.

“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”

Mark Twain

4. Blink

The Power of Thinking Without Thinking  

By Malcolm Gladwell

The lessons in this book are so inspiring yet controversial in a sense. Malcolm Gladwell explores that explores the power of our intuition—arguing that our rational minds can sometimes land us into trouble. He says, “The key to good decision making is not knowledge. It is understanding.” This book is an exciting book that will challenge whatever notion you have of rational thinking and good decision making.

“When making a decision of minor importance, I have always found it advantageous to consider all pros and cons. In vital matters, however, such as the choice of a mate or a profession, the decision should come from the unconscious, from somewhere within ourselves. in the important decisions of personal life, we should be governed, I think, by the deep inner needs of our nature.”

Sigmund Freud

5. Freakonomics

A Rogue Economist Explores the Hidden Side of Everything 

By Steven D. Levitt and Stephen J.Dubner

This is a book written by a remarkable economist and a journalist. The ideas in the book will shock you most of the time. The authors explore everyday topics from a unique perspective coupled with a genuine curiosity to learn the real truth. This book feels like an attack on conventional wisdom, and how much blind faith we have in it. The authors write, 

“The conventional wisdom is often wrong. Crime didn’t keep soaring in the 1990s, money alone doesn’t win elections, and—surprise— drinking eight glasses of water a day has never actually been shown to do a thing for your health. Conventional wisdom is often shoddily formed and devilishly difficult to see through, but it can be done.”

This book is full of so many interesting questions and answers that have been beautifully written. After reading this book, you will have a different outlook on the world, and you will start to question just how much of the conventional wisdom you’ve been taught to believe is true.

Other activities that keep a conversion interesting;

Sharing riddles, playing games like truth or dare, sharing jokes and stories, are also other ways to keep a conversation very interesting. The spontaneous inclusion of these activities into your conversation keeps things more interesting

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