How to Have a Conversation

Conversation. It’s a gift and a skill. Remember when we bestowed the honor of “good conversationalist” on friends, family, and even strangers who looked us in the eye and practiced the art of give and take in conversation?

As digital content pervades our lives, we’ve lost the magic of conversation. At the airport, on the bus, even at a party. Maybe it’s just me, but talking to people can be hard!

If you struggle with making conversation or meeting new people, here is an extensive list of questions you can use to show your interest in people, get to know them better, and make friends!

If you were to be reborn again, whom would you like to be and why?

Has there been any incident in your life, which you think has had an impact on the way you think or live your life?

If you were granted a wish to become any of the superheroes, which one would it be and why?

What is the weirdest and craziest thing you have ever done in life?

If you could star in any movie, what movie would it be?

How should success be measured? By that measurement, who is the most successful person you know?

What is your guilty pleasure?

What benefit do you bring to the group when you hang out with friends?

What do you fear is hiding in the dark?

What do you do to improve your mood when you are in a bad mood?

What three adjectives would you use to describe your childhood?

What do you think about death? What do you believe happens after we die?

For what in your life are you most grateful?

If you could travel back in time to any point in your childhood and give the younger version of you a message, what message would that be and how old would you be?

What are the biggest stresses that you’re currently facing in your life today? What keeps you up at night that I may not know about?

Who can you count on these days as a real source of support for you?

What bothers you most about other people?

Tell me about a coworker you really got along with, and why you think you got along so well?

What’s something you can teach me?

Where do you feel most at peace and ease in the world?

If someone gave you enough money to start a business—no strings attached—what kind of business would you want to start?

If you ran your own company, what kind of people would you hire?

How would your parents describe you?

When you think about the future, what do you imagine?

What could a person do to make you feel supported?

At what point in your childhood did you feel the happiest?

If I could spend a typical day in your shoes, what would I experience?

If you were going to write a book, what would it be about?

What was the last positive thought you had about me?

What was your favorite class in high school?

Which of your friends is most like you? How?

Do you ever wish I could read your mind? When?

What is the grossest thing you have ever had to do?

What did you learn new today?

What are you really excited about right now?

What is the nicest thing anyone ever did for you?

What makes you sad?

What makes you feel joy?