100+ Deep Icebreaker Questions

By: Naveen B

We’ve all been there. You’re having a conversation with someone on a date night, at work, at a party, or in a family setting and they say something that leaves you wondering.

But instead of asking them the deep icebreaker questions right then and there, you decide to wait until later.

But then later never comes because you’re too sensitive or too nervous to initiate that deep conversation.

 I’m a big fan of asking deep icebreaker questions in any social situation.

They can spark great conversations, help you understand your boyfriend, girlfriend, partner, family members, or coworkers’ perspectives, and make it easier to get to know people who might otherwise seem distant or intimidating.

Also read: 500+ Icebreaker questions for any social situation

I also like to ask questions that are fun, thought-provoking, and maybe even a little bit challenging. I’ve found that these kinds of questions can really get people thinking about their lives in new ways — which is something we could all use more of in our everyday life.

So here is a huge list of deep icebreaker questions that can help you make more interesting connections at any place.

Deep Icebreaker questions


The following lists are some amazing deep icebreaker questions to ask to build connections:

1. What is the worst thing about being a human?

2. What are you most grateful for in your life?

3. What do you think is the most interesting thing about yourself?

4. If you could have any superpower, what would it be and why?

5. If you could time travel back to any period in history, when would that be and why?

6. If you had to live one day over again in your life, which would it be and why?

7. What is the biggest regret in your life and how have you learned from it?

8. Which historical figure do you admire the most? Why?

9. If you could go back in time and meet anyone alive or dead, who would it be and why?

10. If there was a billboard above your head with one message for everyone who saw it, what would that message be?

11. What’s something funny that happened to you recently (that’s not too embarrassing)?

12. If you could invite anyone to dinner with no limitations on who they were or when they lived, who would come over for dinner and why?

13. What are you going to do with the rest of your life?

14. What would you do if you won the lottery?

15. Would you rather live in a world without music or without books?

Also read: 200+ Deep Conversation Starters (On deep topics to break the ice)

16. Who is your favorite historical figure?

17. What is one thing you know about me that I don’t know about myself?

18. Do you believe in karma? If so, how has it affected your life?

19. What is something you believe with all your heart but have no proof for it?

20. If there was a monster under your bed, what would you do about it?

21. If you had a time machine, where would you go and why?

22. If aliens came down from the sky and offered everyone on earth eternal happiness, would people accept their offer even if it meant giving up everything they have known beforehand (all their memories and experiences)? Why or why not?

23. What is one thing that has made a lasting impact on your life?

24. If you could go back and change one thing from your childhood, what would it be and why?

25. Why do plants need sunlight to grow but animals don’t even though they both come from the same source (which is energy from the sun)?

Also read: 900+ Questions to ask people (huge list of topics for deep conversation)

Deep icebreaker questions for adults


The following are some deep icebreaker questions for adults that make people think:

1. What causes global warming?

2. How much would it cost to build a Death Star?

3. How do you feel about the theory of relativity?

4. How do you feel about the Big Bang Theory?

5. What is your opinion on string theory?

6. What is your opinion on man-made climate change?

7. Do you believe in aliens or extraterrestrial life forms? If so, what kind of alien would you like to meet and why?

8. Do you believe in ghosts or paranormal activity? If so, what type of ghost would you like to meet and why?

9. Do you prefer sleeping alone or with someone you never met?

10. What is the purpose of your existence?

11. Why are you here?

12. What happens when we die?

13. Is there a God? If so, what is his or her name? What does he or she look like?

14. Is there an afterlife? What will it be like? Where do we go after we die? Are we reincarnated or just gone forever? Is there a heaven and hell and where are they located (if so)?

15. Can time travel be possible someday in the future (if not already)? If so, how does that work exactly and how can we get there as quickly as possible (and what about our friends and family who aren’t going)?

Deep icebreaker questions for work


Here is a list of deep icebreaker questions for work:

1. What do you love doing most in life?

2. What’s your biggest regret so far?

3. How would you describe yourself in three words?

4. If there were no limitations, what would you like to do more than anything else?

5. What has been the biggest challenge in your life so far and how have you overcome it?

6. Why does a car’s engine have to be so loud? It seems like it would be more efficient if it was quieter. But then again, I guess it could also be dangerous if it was too quiet.

7. Why do most people prefer cold water over warm water? Is there an evolutionary reason behind this preference? Or is it just because we grew up drinking cold water?

8. How come some people feel tired after exercising while others don’t? Is it because of how much we exercise or something else?

9. Why do people get sick when they travel but not when they stay home? Is it because their bodies are used to the germs in their own environment?

10. How did life begin on Earth billions of years ago and how did it develop from simple cells into more complex organisms like humans over millions of years of evolution (and why did it take so long for us to evolve)?

11. If aliens exist out there somewhere in the universe, how did they get here (and why haven’t we seen any signs of them yet)?

12. Who are the three most important people in your life right now? (not family)

13. If you could live anywhere in the world, where would it be?

Also read: 750+ Conversation starters on topics for any situation (Your ultimate questions list)

Deep icebreaker questions for small groups

These are some deep icebreaker questions for small groups:

1. What is the point of living?

2. What is going on in the human brain when we dream?

3. Why does time seem to pass at different speeds?

4. Is there any limit to how much information the universe can hold?

5. What is consciousness, and can it ever be quantified?

6. Is there such a thing as a “universal language”?

7. Are humans more alike or different from one another?

8. How did life originate on Earth?

9. How do we define intelligence, and what are its limits?

10. Does free will exist — or is everything predetermined by outside forces?

11. Do we have an innate sense of morality (and if so, how did it develop)?

Deep icebreaker questions for dating


Here is a list of the best deep icebreaker questions for dating:

1. “What is your idea of a perfect date?”

2. “Do you believe in soulmates or twin flames?”

3. “What is your opinion about the concept of love at first sight?”

4. “Would you rather be rich or happy?”

5. “Which do you prefer: having sex or making love?”

6. “How do you feel about cheating?”

7. “Is there anything that would make you leave me?”

8. “What kind of relationship do you want to have with me?”

9. “Do you think it is possible to fall in love with someone after just one meeting?”

10. “Are you afraid to fall in love again because of past breakups/heartbreaks/relationships that ended badly for you?”

11. “If I ask where your ex lives and what he/she does for a living, will it upset you if I say I want to meet them someday?

Also read: Dating Questions 101: Conversation starters topics for online, first & second date nights

Deep icebreaker questions for couples


These are some good deep icebreaker questions for couples:

1. How do I know if he/she is the one?

2. Why do some people cheat on their spouses?

3. How long do most marriages last?

4. Is it okay to get a divorce?

5. What are simple ways to save your marriage?

6. If a man has an affair with another woman and then comes back to his wife what do you think makes his return?

Is it because he wants to be with her or because he wants a home and kids or both? Or something else entirely?

7. Do you feel like there is someone out there who is meant for you?

8. Do you believe in twin flames? And what do you think is the purpose of a twin flame relationship?

9. What are the pros and cons of being in a  relationship?

10. Is it possible to have more than one twin flame at the same time?

11. Can people be reincarnated as another person or animal from their past lives? How long does it take for two people to fall in love with each other?

12. Why do some people stay together for so long while others struggle through life alone despite having everything they need or want in their lives already

13. Do you believe in soulmates?

14. What makes you happy?

15. Is there a reason why we are here?

16. Are we alone in the universe?

17. Is war inevitable?

18. How do you define success?

19. What is the most important thing you have learned in your life?

20. If money was not an issue, what would you do for a living?

Also read: 200+ Questions for couples (Build long-lasting deep relationship)

Deep thinking icebreaker questions

Here is a list of deep thought icebreaker questions

1. What is the meaning of life?

2. What is the purpose of life?

3. Do you believe in God? Or anything else greater than yourself?

4. Can you explain the difference between right and wrong?

5. Why do we have to die?

6. Is there an afterlife? Can you prove it to me?

7. How do you know that you are right and I am wrong? (If they say “because I just do” ask them why they think that)

8. Does God exist outside of your mind, or is he just a construct created by your mind?

If so, why do you believe in him/her/it so strongly if he/she/it doesn’t exist outside of your mind? If not, how can he/she/it be real if there is no physical evidence for his/her/its existence?

Why does it matter what someone else thinks about God when it has no impact on reality whatsoever?

9. If you had to choose between a house that was haunted or a house that had a secret room, which would you choose?

10. What do you want to ask me but don’t know how or why?

Icebreaker Deep talk questions

These are some great icebreaker deep talk questions:

1. How do you define loneliness?

2. If you could go back in time and kill Hitler, would you do it?

3. When was the last time you had a bad day?

4. What are your biggest regrets in life?

5. What would you do if you knew you couldn’t fail?

6. If money were not an issue, what would you want to do with your life?

7. Do you think we are alone in the universe or are we surrounded by extraterrestrial beings that don’t want to be discovered yet? (This is a fun one!)

8. If you could go back in time and give yourself advice when you were younger, what would it be?

9. What’s something about yourself that others wouldn’t know just by looking at you/talking to you for five minutes/etc.? (This question can be really fun to talk about because people often reveal things about themselves that they don’t usually talk about.)

10. If you had the choice between being famous or being rich, which would you choose?

Photo of author
Experienced Psychology and philosophy Writer, self-help and relationship Coach and thought influencer. He has 7 years of experience in Personal development industry. His expertise as a self-help and relationship Coach has been highlighted through his articles in medium and substack to name a few. To be updated with his latest work, connect with him by following his social media accounts.

Leave a Comment