20+ Deep Conversation Starters And Topics To Engage With Someone For Hours Upon Hours | Uncustomary

20+ Deep Conversation Starters and Topics to Engage With Someone for Hours Upon Hours

Do you hate awkward and uncomfortable silences? Most people squirm when the conversation stops and your mind goes blank. 

It’s not always easy to keep the conversation going with other people. Even when you’re surrounded by close friends or loved ones, conversation topics can falter.

Everyone gets bored with small talk after a while. Chatting about the weather or what you did at the weekend can get exhausting quickly too.

Are you eager to hear which deep conversation starters could keep you talking until the early hours? Check out more below!


1. Do You Consider Yourself a Spiritual Person?

More and more Americans consider themselves to be “spiritual but not religious.” In fact, around one-quarter of us say we’re spiritual without being a part of a religion.

By talking with other people about spirituality and what this means can keep your conversation going for a long time.

2. How Would You Spend Your Last Day on Earth?

You don’t imagine that you’re going to die tomorrow. But, if we lived as though every day on Earth was our last, how would it be different?

Would you spend time with your loved ones? What crazy thing would you get up to if nothing mattered anymore?

3. What is the Most Important Thing You Learned From Your Parents?

Many people are thankful for their upbringing. Your parents probably taught you a lot about the world. But, what was the most important lesson they gave you when you were growing up?

4. What Would You Change About Your Country?

You may think that your country is the greatest in the world, or that it has a lot to improve for now. But, even then, it’s never going to be perfect.

What needs to change to fast in your humble opinion can be a great way to explore other people’s views of the world.

5. Which Famous Person do You Idolize and Why?

Maybe your idol is a historical figure like Abraham Lincoln or a modern-day heroine like Meghan Rapinoe. Who is it and why? 

6. What do You Think is the Most Important Issue of Our Time?

Are you most concerned about global warming, poverty or disease? There are so many important issues to worry about. 

7. What is Your Biggest Weakness?

This is a trademark interview style question. But, people’s answers to this kind of question are so fascinating when you want to learn about someone.

8. What Did You Learn From Your First Love?

Many people say that there is something special about your first love. We all learn a lot from that relationship in high school or college. What did you learn?

9. Where in the World Would You Like to Visit?

Around 60 percent of Americans say they a particular destination in mind that they would like to visit.

Have you always dreamed of going on a safari in Kenya or having a city break in Paris? This is a great question for conversations.

10. What Are You Most Proud of?

People are proud of different things. Maybe you have experienced a successful career or you were a proud father or mother.

11. Do You Find it Hard to Live in the Moment?

Living in the moment isn’t always easy. But, some people find it easier than others. 

12. What is Your Biggest Fear?

Are you scared of death? Do you fear public speaking in front of a crowd? There are numerous things to fear in the world. 

13. What do You Value in Friendship?

Having no friends is awful. Friends make our lives happier and healthier. But, what do you look for in a good friend?

14. What Time in History Would You Like to Travel to?

Do you fantasize about living during ancient Greece? Are you romantic about the 1960s? This is a great question to learn about other people’s nostalgia.

15. What Would You Do if You Won the Lottery?

Who wouldn’t want to become a millionaire? Many people say they would travel the world or buy a huge house. It’s great to hear what others would do.

16. What Advice Would You Share With a Younger You?

Everyone makes mistakes during their youth. Imagine if you could go back to your younger self and share some wisdom.

17. Are You a Superstitious Person?

Over one in four Americans say that they’re superstitious. Whether you believe in master numbers or astrology, it’s interesting to hear about it.

18. If You Could Speak Another Language, What Would it be?

Many people only speak one language. But, what if you could instantly be able to speak another foreign language? Maybe you want to be able to converse in Chinese or have a chat in French.

19. What is the Best Book You Ever Read?

Most people have been inspired by a book in their lifetime. You can discover a lot about someone by hearing about their reading experience. 

20. What Makes You Laugh?

When we laugh, endorphins are released and we feel better. But, a sense of humor is an amazing thing.

But, people laugh at completely different things. You can talk endlessly about the most hilarious things that have happened to you.

Ideas for Deep Conversation Starters

Are you tired of small talk? If you want to really get to know someone, you need to be able to have a deep conversation together. 

That’s why it’s so important to have some ideas about the best deep conversation starters to use. From your favorite time in history to what you value in friendship, there are so many things to talk about. 

Do you want to discover more ways to live a happy life? Check out our website for much more!