80 Deep Questions To Ask To Spark Long Conversations

Are YOU looking for fun topics for your next late-night dinner party?? Then read on! We've collected a list of penetrating, thought-provoking conversation starters, middles, or endings.

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They're great for when you're just getting to know someone or when you decide suddenly that you want to learn more about your friends. Some of these will really make you think, but don't be afraid. There are no wrong answers!

1.Which do you trust the most: your heart, your brain, or your gut?

2.If you had three wishes in life, what would they be?


3.Where is the scariest place your mind can wander?

4.Does everything happen for a reason?

5.What's your biggest pet peeve?

6.If you had all the resources, time, and land available to build whatever you want (a house, a park, a monument...), what would you build?

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7.What version of yourself would you love to see in 10 years?

8.Where's your favorite spot to cry?

9.Do you think animals have souls?

10.Is it better to go with the flow or fight the current?


11.Do you think you could be happy if you were always single?

12.On the whole, do you think people are good?

13.What fictional character do you relate to the most?

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14.Do you think plants have feelings?

15.What is your biggest regret?


16.Are we born with inherent personalities, or is it entirely the result of our experiences and circumstances?

17.Do you think it's necessary for some people to lose in life so that others can win?

18.What do you find most important in life and why?


19.What does happiness mean to you, and do you think you've found it?

20.How do you define success in your life?

21.What is your most cherished memory, and what makes it so special?

22.Should everyone on the planet be striving toward a common goal? If so, what would that be?


23.What do you think is the purpose of life, if there is one?

24.If you had a million dollars to donate, what charity would you donate to and why?

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25.What are your core values, and how do they guide your decisions?

26.How do you handle failures or setbacks in your life?

27.What is your favorite childhood memory?


28.What is your biggest fear and how does it influence your choices?

29.What is something you wish you could forget?


30.What role does empathy play in your interactions with others?

31.What is the best thing about your personality?


32.Can you recall a moment that completely changed your perspective on something important?

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33.What do you think makes someone your best friend rather than just your friend?


34.How do you see the relationship between love and vulnerability?

35.What constitutes a meaningful life for you?

36.If you could swap bodies with someone for 24 hours, who would it be?


37.What are you most grateful for in your life right now?

38.If you woke up tomorrow and you were a dragon, what do you think you'd look like?

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39.How do you handle regret, and do you have any regrets that have had a lasting impact on you?

40.If you could spend 24 hours inside the world of any painting, which one do you choose and why?


41.What are some qualities or characteristics you value most in people?

42.When was the last time you sang to yourself? To someone else?


43.How do you think your upbringing has shaped who you are today?

44.What do you think is the key to maintaining a strong and healthy relationship?

45.How often do you apologize?

46.What is the most beautiful or awe-inspiring thing you've ever witnessed or experienced?

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47.If you could teach the entire world just one concept, what would it be?


48.What is your perspective on the concept of legacy and the mark you want to leave on the world?

49.What are your thoughts on the balance between individuality and collective responsibility?

50.How do you approach the pursuit of knowledge and wisdom in your life?

51.How do you find meaning and purpose in challenging or mundane tasks?

52.What’s the hardest you’ve ever laughed?


53.How do you think technology is shaping human relationships and society as a whole?

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54.What does emotional connection mean to you?


55.How do you navigate ethical dilemmas and moral gray areas?

56.Who are three of the most important people in your life?


57.What is your approach to dealing with regret and moving forward from mistakes?

58.Do you think every situation has a silver lining, or are some things just completely negative?

59.What role does personal growth and self-improvement play in your life?

60.How do you see the intersection of science and spirituality in your life?

61.What is your perspective on the concept of "good" and "evil"?

62.How do you cope with the pressures and stresses of modern life?

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63.Would you like to be famous? In what way?


64.Have you ever experienced a moment of profound clarity or insight? What was it about?

65.How do you define integrity, and why is it important to you?

66.What do you think is the most significant issue facing humanity today?

67.What is your philosophy on forgiveness, and has forgiveness played a role in your life?

68.What's the first thing you think of when you wake up most days?


69.What role does self-love and self-compassion play in your life?

70.How do you handle uncertainty about the future?

71.If the universe is expanding, what is it expanding into?

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72.Do you believe in fate or that people have control over their destinies?

73.What's the most significant lesson you've learned from a challenging experience?

74.How did you meet your best friend?


75.How do you find purpose and fulfillment in your daily life?

76.How do you envision your ideal future, both personally and for the world at large?

77.If you could get any question answered (other than what is the meaning of life), what would it be?


78.What’s keeping you up at night?

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Jacob Wackerhausen / Getty Images

79.What went right with humanity? What went wrong?


80.If you could go back in time and give your younger self one piece of advice, what would it be, and why?

This post contains contributions from Anjali Patel and Natalya Lobanova. This post was enhanced using AI-powered creativity tools. Take our new AI-powered quizzes here.