101 thought-provoking questions to ask about life, love, and everything in between

Have you ever been asked a question that’s left you a little puzzled? A faint hum, followed by an “uhhh…” as the gears stop turning for just a second.

Thought-provoking questions can do that to you.

No, they’re not meant to stump you or leave you tongue-tied; that’s not their purpose. Rather, they exist to shake up your usual way of thinking.

But here’s the problem many of us face: According to Vanessa Van Edwards, a speaker for Science of People and the trainer for Mindvalley’s Magnetic Charisma Quest, we often slip into what she calls “accidentally negative” conversations—things like, “The traffic was terrible” or “This weather’s so hot.”

Now imagine the contrary: Instead of these typical complaints, asking interesting questions can push us to look deeper, consider new perspectives, spark curiosity, and even inspire action. Plus, they’re a great way to connect more quickly and meaningfully with others.

Next time you’re stuck in small talk (because, let’s be real, who actually wants to talk about the weather or traffic?), explore this list. There are 101 questions to truly get to know someone—choose one and see where the conversation takes you.

20 funny, thought-provoking questions

The misconception about thought-provoking questions is that they have to be serious so that they garner meaningful, insightful answers. But funny ones can be used as conversation starters as well.

In fact, research shows that humor not only makes interaction engaging but also helps people feel closer and find common ground. By sharing a laugh, you’re not just breaking the ice; you’re building a connection.

Looking for funny questions to ask? Here are a handful you can consider:

1. If animals suddenly gained the ability to use social media, which animal would go viral, and what would they post?
2. Imagine your life was narrated—who would be the worst choice to tell your story?
3. If your life was a movie, what would be the most embarrassing scene?
4. If you had to choose a theme song that plays every time you enter a room, what would it be, and why?
5. What’s the most ridiculous superpower you’d actually want to have, and how would you use it?
6. Would you rather your thoughts be broadcast for everyone to hear or have no inner voice at all?
7. What’s the most absurd rule you would make if you were suddenly in charge of the world?
8. If emojis were the only way you could communicate, what five would you use the most?
9. What’s the most ridiculous lie you’ve ever told, and did anyone believe it?
10. What’s the weirdest food combination you secretly love?
11. If you could banish one minor inconvenience forever, what would it be?
12. What’s a bizarre talent you have that’s almost useless but still impressive?
13. Imagine the most absurd reason you could get arrested—what would it be?
14. If you had to relive the same awkward moment forever, which one would it be?
15. Describe the warning label that best fits your personality.
16. Imagine you’re a flavor of ice cream—what flavor are you, and what toppings describe your personality?
17. If every time you laughed, something strange happened (like it started raining gummy bears), what would you want it to be?
18. If you could make one of your habits a new trend, what would it be, and how would people follow it?
19. What’s the strangest habit you think aliens would find confusing if they visited Earth?
20. Suppose you could swap your voice with any famous character’s voice—who would you choose?

20 thought-provoking icebreaker questions

There are times when we don’t have all the livelong day to get to know someone—networking events, speed dating, elevator pitches, workshops, seminars, community meetups, charity galas, or fundraisers… the list goes on.

Having a few thought-provoking icebreaker questions ready can be super handy. Not only that, but these questions can also add an element of surprise.

As Vanessa explains in her lesson, “Surprise creates dopamine. We love to be surprised… it keeps our brain engaged.” When we break away from the expected small talk, it keeps things interesting, keeps people curious, and makes interactions more memorable.

So, if they’re expecting talk about the weather or traffic, try throwing in one of these questions instead:

21. Is there a book or movie that’s influenced your perspective on life?
22. What’s a life lesson you’d say everyone should experience firsthand?
23. What’s an underrated quality you appreciate in others?
24. Who’s been a big influence in your life, and how did they shape who you are today?
25. Have you ever done something that totally surprised you?
26. What’s a small change you made in your life that made a big difference?
27. Is there a passion or hobby you’d love to explore more?
28. In your opinion, what makes a friendship truly meaningful?
29. How do you personally define success, and has that changed over time?
30. If you could start any career tomorrow, what would you want to do?
31. Is there something you wish people understood about you?
32. What’s one compliment you received that really stuck with you?
33. If you could have dinner with a historical figure, who would it be?
34. What’s the one belief or value that matters most to you?
35. If you could witness any historical event, which one would you choose?
36. Is there a goal you’re working toward that’s especially important to you?
37. If you could make one change in the world, what would it be?
38. What’s a skill you’ve developed at work that’s unexpectedly helped you in your personal life?
39. What keeps you motivated when things get tough?
40. What’s a moment in your life that totally changed how you see the world?

20 thought-provoking questions for couples

When you’re starting to get to know someone, it’s natural to be inquisitive. But, as many couples know, conversations can hit a wall.

Vanessa suggests asking yourself, “How do you want people to feel before, during, and after interacting with you?” Thought-provoking questions can help you set that tone—whether it’s a sense of excitement, warmth, or simply comfort—so that both of you walk away feeling closer and truly appreciated.

These questions help you move past the small talk and dive into more mindful communication that may just reveal things you didn’t know about each other.

41. What’s one thing you’ve always wanted to try together but haven’t yet?
42. What’s something you’re really proud of but don’t share with others often?
43. If we could live anywhere in the world for a year, where would you choose?
44. What do you think is the most important quality in a strong relationship?
45. Is there a book, movie, or song that makes you think of us? Why?
46. How would you describe the perfect day together?
47. If you could change one thing about the way we handle conflicts, what would it be?
48. What’s a small thing I tend to do that makes you feel loved?
49. Is there something about your childhood you’d like me to understand better?
50. What do you think our life will look like in 10 years?
51. If you could accomplish one big goal this year, what would it be?
52. What’s a moment in our relationship that made you feel truly loved?
53. How do you like to feel more supported during tough times?
54. What’s one thing you want us to focus on more in our relationship?
55. What do you think our biggest strength is as a couple?
56. How would you describe your ideal future for us?
57. What’s one value or lesson you hope we pass on to our kids (or future generations)?
58. Is there a part of your life you feel I don’t know much about yet?
59. How would you define “home,” and how does it feel with us?
60. What’s a tough experience that you feel made you a stronger person?

20 thought-provoking questions for kids

It’s no secret that kids are naturally curious. Parents know this all too well, facing an endless stream of questions about everything and anything.

“What is this?”
“Why does it do that?”
“How does this work?”

While answering these questions can be a handful, asking them back some can be just as powerful. Research shows that thoughtful questioning can spark curiosity and help children build on what they already know, guiding them to new ideas and understandings.

By asking your little ones questions that make them think, you can give them a chance to explore, imagine, and develop important skills—while having fun, too.

61. Imagine you could have any animal as a pet, even a wild one. Which would you choose, and why?
62. I’m curious—what’s one thing you’d love to learn more about?
63. What’s the most amazing thing about being human?
64. A time machine appears in front of you. Do you go to the past or the future? Why?
65. Can you think of the nicest thing someone has done for you, and how it made you feel?
66. Imagine you could invent something to make life easier. What would it do?
67. Is there something you’d like to teach others?
68. Tell me about one thing that always makes you laugh.
69. Picture yourself spending a day with any famous person. Who would you choose, and what would you do together?
70. What’s something you’ve done that makes you really proud?
71. What’s something you’d love to try, even if it seems a little scary?
72. Describe your idea of the perfect day from start to finish.
73. Suppose you could only eat one food for a whole week. What would you choose?
74. Imagine you could change one thing about the world. What would it be?
75. Let’s create a new holiday. What would it be all about?
76. Tell me about a big goal you have and what might help you reach it.
77. A friend is feeling sad. What would you do to cheer them up?
78. Can you think of something you learned recently that surprised you?
79. What’s something you think adults don’t understand about kids?
80. In your opinion, what makes someone a good friend?

21 thought-provoking questions about life

Chances are, you’ve asked or been asked, “How’s life?” … to which the response is typically, “Okay.”

Riveting. (Sarcasm, obviously.)

But, as Vanessa points out, “when you’re asked about things that make you feel excited, you actually produce dopamine.” These questions get a person’s brain off of “autopilot” and instead dive into ideas they might not normally consider.

For example, instead of asking, “How’s life?” try something like, “What’s been on your mind lately?” This can be a great way to start a conversation that feels fresh and meaningful.

With that in mind, here are a handful of deep questions to ask if you want to skip the usual small talk.

81. Think back to a belief you held strongly in the past—how did it change, and what shifted your perspective?
82. Tell me one thing that people often assume about you but isn’t true.
83. What’s the best piece of advice you’ve ever received?
84. Imagine having a conversation with your future self—what’s the one thing you’d be eager to know?
85. Picture yourself spending a day in complete silence. How do you think it would affect your thoughts?
86. What’s something you wish people would ask you about more often?
87. Describe a risk you didn’t take but still think about now and then.
88. Looking back, is there something in your life that felt like a mistake but turned out to be a blessing?
89. What would you say has been the biggest “plot twist” in your life so far?
90. Imagine telling a single story from your life to a stranger. Which story would you choose, and why?
91. Share a moment you look back on now with gratitude, even if it was challenging at the time.
92. If someone retold your life as a myth or legend, what would be the main lesson in the story?
93. In your opinion, what’s one way technology could redefine what it means to be human?
94. What do you see as humanity’s greatest challenge for the future?
95. How do you think artificial intelligence will shape human relationships in the years to come?
96. Which traditions or customs do you hope future generations will carry on?
97. Looking to the future, what’s something you think future generations might wish we’d done differently?
98. If you could share one piece of wisdom with the next generation, what would it be?
99. Picture yourself living anywhere in the universe—where would you go, and what would you hope to find?
100. Choose one mystery of the universe you’d like to instantly understand. Which one would it be?
101. What’s your greatest hope for humanity’s future?

Spark conversations that matter

We’ve all been there—stuck in a chat that’s going nowhere or recycling the same old “What’s up with this weather?” or “How about that traffic, eh?”

Thankfully, you now have this list of 101 thought-provoking questions that can change that and open doors to conversations that matter. And when you want to take your conversationalist skills up a notch, you can add to them by downloading Mindvalley’s The Connection Kit. 

This beautiful and colorful deck isn’t just for deep thinkers; it’s for anyone who wants to bond, whether you’re chatting with family, friends, a new love, coworkers, or even kids and teens. As Vanessa points out, these questions help you “sub out autopilot questions for dopamine-producing ones.”

So, ready to say goodbye to awkward silences (or, at least, superficial interactions)? Download your free deck and bring on the meaningful conversations.

Welcome in.