71 Open Ended Questions Examples for an Engaging Conversation

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Meeting a stranger for the first time can be awkward. Yet, we are all strangers until we really get to know each other better. Sometimes, the only way to really get to know someone is to ask questions.

That said, knowing which questions are appropriate and which will give you some insight into the other person can be challenging. I mean, there are only so many ways you can discuss the weather before you become bored… so diving in deeper can be the best way to really get to know someone.  Questions can be great conversation starters, and this list of open ended questions examples will help you get more than a “yes” or “no” answer, which doesn’t really reveal much about a person.

Open Ended Questions and Closed Ended Questions: What Are They and What is the Difference?

A question can have many answers, but some questions can only be answered with a “yes” or “no.” Questions that encourage conversation are open ended. Questions like “What did you want to be when you were a child?” and “What is your favorite food and why?” are open ended questions examples where your conversational partner is encouraged to explain their answer or reason about the question. This makes for a bonding experience and shared discussion that validates the other person

There are not many interpersonal benefits to asking a closed ended question. They are more designed for functional dialogue. Questions such as “Can you show me where the office is?” can start the connection or conversation, but it doesn’t tell you much about the other person. These questions typically have “yes” or “no” answers, or very brief and simplistic responses.

Open ended questions have the benefit of encouraging creative responses and real self-expression. With a conversation based on open ended questions, you keep placing the ball back in the other person’s court. 

Asking closed ended questions will lead to short and abrupt answers, unless you follow up with open ended questions examples like:

  • “Have you worked here for many years?” “What’s good about working here?”
  • “Wow, this gym is amazing! Do you come here often, and which of the trainers would you recommend?”

With open ended questions, you can learn more about the other person and keep things going as you discover each other and become friends. This is the beauty of real social exchange. 

Following up a closed ended question with an open ended question can help develop the conversation. I’m going to give provide you with a list of 71 comprehensive open ended questions to get the conversation going and keep it that way.  

Open Ended Questions Examples

To help you decide which questions are best to try out, I’ve divided these questions according to topics of conversation and unique settings. Have fun, be sure to listen to the answers, and build on these with more open ended questions. This is how conversations work and how you get to learn more about people. 

Questions for Social Settings 

Hanging out with people you don’t really know yet can be really challenging, and this is where you need a few ice-breaker questions. These are fun to use at social events like a game night or going out for dinner.

  1. What are your plans for the weekend?
  2. I’m planning on going to the mountain/park/beach soon; what are your favorite holiday destinations? What’s great about them?
  3. My pets are such a part of my family; what pets do you have?
  4. I love the food here; what’s your favorite dish?
  5. Have you always lived here in (city name), and what do you like about it?
  6. I just love Easter/Christmas/Halloween/Hanukah/Thanksgiving; which is your favorite and what does your family do over the holidays?

Questions for New Friends 

Once you know someone a little better, you move past the casual chat and start to really find out about them and what makes their world go round. Open ended questions examples are a great way to learn about them and become even better friends.

  1. When you were a kid, what were your dreams—what did you see yourself doing and why?
  2. What’s the thing that’s made you the most proud?
  3. I have a pet peeve; can you guess what it is?
  4. What is a huge hit in our society that really annoys you?
  5. What colors do you prefer to wear together?
  6. Do you have any pets, and what’s their story?
  7. If you could, which animal would you like to be?
  8. What is your favorite pastime?

Questions for New Colleagues

While you may not always become friends with your colleagues, it does help improve your ability to network and work with them when you know a little bit more about them and how they think. Having open ended questions examples to help you learn about your colleagues will help you build better working relationships, even if they are difficult people.

  1. Do you consider yourself a very organized person?
  2. What are your favorite things to have on your desk at your workspace?
  3. What’s the scariest work-related experience you’ve ever had?
  4. Who do you look up to in your life?
  5. Do you go away over weekends? Where do you go?
  6. Do you follow the news? What did you think about (an event in your area or country that is interesting but not political)?
  7. I love my coffee/tea/soda/water in the morning: what drink get you going in your day?
  8. If you could make something from a hundred years ago popular again, what would it be and why?
  9. What do you think is most important, honesty or caring for others?

Questions about Food and Flavor 

Food, drink, songs, and entertainment are the spice of life. Asking questions about these can really help you connect to other people and start conversations. It’s time to unplug and discover your senses.

  1. What is your favorite end-of-the-month food to eat?
  2. If you could meet one band, who would you meet and what would you say to them?
  3. What sport did you participate in as a child, and what is your favorite sport to watch now?
  4. If an alien landed here from another planet, and they laid out a feast of strange food and drinks, would you eat it and how do you imagine it might taste?
  5. What food didn’t you like to eat as a child, and do you eat any of this today?
  6. If you could only eat one thing for the next year, what would it be?
  7. What food would you never want to eat again in your life?
  8. How important is it to smell your food, and what smell is your favorite?

Questions for Awkward Situations 

When you are caught in an awkward situation, you will need to talk to the other person. At times, using humor can really help you learn about the other person while bridging awkward situations. 

  1. What do you fear was hiding under your bed as a child? What’s hiding there now?
  2. Do you curse often? What is your choice phrase for challenging situations?
  3. Have you ever had someone save your life? Did you ever save someone else’s life?
  4. Do you think guilty pleasures are important? What’s your guilty pleasure?
  5. If you could change your name, what would you call yourself?
  6. How much time do you spend online in a day? What is your favorite online site to visit?
  7. What do you want to accomplish before you die one day?
  8. What’s the craziest pet name you’ve ever been called, and how would being that pet be the solution to your current dilemma?
  9. Name the worst possible or most embarrassing skill you’ve perfected and explain why you’re proud of that skill.
  10. What TV series do you see yourself living in one day when you are sucked into your TV?
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Out-of-the-Box Questions 

When you’re stuck at a boring meeting or party, you may find an opportunity to use a perfectly random question that is so out of the box that it enlivens the group and makes for interesting discussions.

  1. Which celebrity or historical figure would you want to be stuck in an elevator with? Who would you absolutely hate being stuck in an elevator with?
  2. What traditions or strange beliefs have you seen with some people?
  3. Will you show me a strange or weird talent you have?
  4. If you could be anything on earth except a human and an animal, what would you be?
  5. Which characteristics of a cartoon character do you wish you had?
  6. Do you believe movies have the power to change the world? Do you perhaps believe books have more power to do so?
  7. What is the power of music? Describe what you think our world would be like without music.
  8. Do you think robots will take over the world one day, or will we live better because of robots?
  9. Do you have an embarrassing piece of clothing in your closet at home?

Questions for Age Differences 

Age can divide or unite us. By asking about someone’s age, you can either offend them or draw them into interesting conversations. It all comes down to how you ask, not always what you ask. Try these open ended questions examples and be amazed by the answers:

  1. What was your favorite age to be and why?
  2. What’s the best thing about getting older?
  3. Describe what you miss most about being young/younger?
  4. Tell me about the most outrageous thing you’ve ever done and how it felt? Now that you are older, would you do it again?
  5. Which words of wisdom would you say to your younger self? What would your younger self say to you now?
  6. Would you choose immortality or living a shorter but fuller life?
  7. When you see yourself retiring, what do you want to do when you stop working professionally?

Questions for Lovers and Partners

This may seem really tricky, and while the obvious questions for a lover and partner may include whether they’re safe and if they love you, there are some other non-sexual questions you can also start your pillow talk with. 

  1. What’s the most exciting evening you’ve ever had?
  2. What is the most romantic gift you’ve ever received? What do you like to give as a romantic gift?
  3. How important is love to you when it comes to relationships?
  4. What is your favorite post-love-making activity to do?
  5. Which are your favorite body parts, and what would you replace them with if you were a machine?
  6. Is being faithful more important than being reliable in a relationship?
  7. If you had one last breath left, what would you say with that breath, except “I love you?”

Questions about Life and Death 

Finally, life and death are topics that we are always aware of. Asking people how they feel about these and think about life and death will give you a deeper insight into their beliefs, feelings, fears, and convictions. Be sensitive when you ask and how you respond to these topics as people are all entitled to their own views and beliefs. 

  1. What do you think is waiting on the other side of death?
  2. If you had to live your life again, what would you change? What would you keep the same?
  3. What do you think is your reason for living?
  4. Each of us leaves or would like to leave a legacy when we die. What is yours?
  5. What did you enjoy most about living? What do you fear about dying?
  6. If you had to choose how you died, what would you choose?
  7. What would be said at your eulogy?

Final Thoughts on Open Ended Questions Examples

Asking questions is how you learn about people, and it allows people to open up and share. Communication doesn’t always come easily to everyone, but with a couple of great questions, you can survive any situation… no matter how awkward. 

Learn to have conversations that reveal a person’s true self and let them get to know you, instead of manipulating people into artificially liking you. 

Finally, if you want to ask better questions, then watch this short, 20-minute course to learn how to have a great conversation with virtually anyone.

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71 Open Ended Questions Examples for an Engaging Conversation