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The Definitive List Of Deep Conversation Starters

If you feel intimidated by deeper more open ended conversations, that's totally normal. Here's why you should trash that mindset and dive in.  08.02.24

two girls laying on old car talking

Why Even Have A Deep Conversation?

Relationships are a lot like plants, if left unwatered for a prolonged period, they die. They need to be nurtured and stimulated to grow. Deep conversations are based on vulnerabilities, curiosities, fears, and imperfections. They can showcase a side of us that's normally tucked away. We don't necessarily share these thoughts because the topics are never brought up in our everyday conversations. These are the things that are hard to talk about because we can feel uncomfortable. Topics like sex, death, finance, religion, and mental health. Philosophical questions that challenge the meaning of life and our purpose. Whether we talk about it or not, we humans all share the same questions about existentialism.

In our daily lives, we usually stick to small talk and surface-level subjects, because let's be honest, they're easier. "This weather today is amazing." or "Did you catch the game yesterday?" If you really want your bond to strengthen between you and someone else then this list of questions is a good starting point. Both deep and philosophical in their nature, they will help provoke conversations that are typically untouched. It's hard to say we actually know someone without exploring these thought-provoking questions.

couple looking out car at the ocean

The List

1. What's the meaning of life?
2. What are your passions?
3. What are your biggest fears and why?
4. Do you believe in a higher power?
5. Define happiness for you?
6. Can we really know anything?
7. Is it easier to love or be loved?
8. Do you love yourself?
9. What feels hard in your life right now?
10. What do you think about therapy?
11. When do you feel the most alive?
12. Are you an introvert or an extrovert and why?
13. What are three things you couldn't live without?
14. Does your family know the real you?
15. How do you value family?
16. What's your opinion on religion?
17. What does sexual fulfillment mean to you?
18. Why did your past relationships fail?
19. Can spirituality make you a happy person?
20. Are we a minuscule part of intelligent life in the universe | Do aliens exist?
21. For what in your life do you feel most grateful?
22. If lying is wrong, are white lies okay?
23. If money cannot buy happiness, can you ever be truly happy with no money?
24. What happens after we die | Is death a new beginning?
25. Do you want to have kids or not?
25. Is humanity doomed to head in a destructive direction?
25. Is torture ever justified? | Death penalty?
25. Has social media had a positive or negative impact on society?
25. Has the internet brought us closer together or further apart?
25. What is the difference between a good and bad person?
25. Are you happy?
26. Are people born with a specific personality, or are they the result of their circumstances?
27. What is time?
28. Is friendship necessary for happiness?
29. How can you distinguish art from something that isn’t art?
30. Is it ever okay to break the law? When?
31. Do animals have souls?
32. What makes you, you?
33. Do guns protect people or kill people?
34. Can memories be erased?
35. Is there really any completely selfless act of kindness?
36. How much does language affect our thinking?
37. Are people ethically obligated to improve themselves?
38. If everyone spoke their mind, would the world be a better place?
39. Are highly intelligent people less happy than individuals with average intelligence?
40. Does fate exist?
41. Does free will exist or are all events and actions predetermined?
42. How does one find purpose in life?
43. What's more important: doing the right thing or doing things right?
44. Is AI going to screw humanity over or is it a good thing?
45. How do you distinguish right from wrong in a subjective world?
46. What is human consciousness?
47. Can you describe a time you cried in front of another person?
48. Does luck actually exist?
49. Do computers have the ability to be creative?
50. What should the goal of humanity be?

guy and girl laying by river talking

Getting Deep With Strangers

Deep conversations aren't just for family and friends. You can strike up a conversation with a stranger and you might be surprised at how it will go. We tend to attach the word "awkward" to the idea of holding a meaningful conversation with someone we don't know. But as I said earlier, we are all human and all dealing with the same sh*t, right? You think that a stranger might not care or show any empathy, but more often than not, they do. On top of that, we can feel more interconnected with the world around us when we hold these conversations. It can all start from a simple hello.

In fact, according to a recent study published in the Journal of Personality and Social Psychology, they discovered just that: Conversations between strangers felt less awkward, and created more connectedness and happiness, than the participants themselves expected. It's like it's almost easier to go into depth because you know you may never see them again, so you're more likely to open up and show your vulnerable side. In turn, you get this little touch of joy seeing that you are not alone in this world.





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