Deep Questions to Get to Know Someone: 100 by Stage

The short answer: the best deep questions to get to know someone are open, personal without being intrusive, and matched to how well you already know each other. On a first meetup, “light-deep” questions such as “What’s something you’re proud of that most people don’t know?” work well. By the second or third meetup you can ask about values, turning points and what matters to them. The heaviest questions belong with close friends and partners. Below are 100 deep questions organised by stage, the questions to avoid early on, a note on the well-known “36 questions” study, and a worked example of how to go deeper without it feeling like an interrogation.

These work for dates, new friendships and old friendships you’d like to get closer in. The rule of thumb is simple: go one step deeper than the conversation you’re already having, answer your own questions too, and let the other person decide how much to share.

How to ask deep questions without it feeling intense

• Earn the depth. Start with lighter conversation first. If you need openers, our list of first date conversation starters has 60 easy ones. Deep questions land better 30 minutes in than in the first five.
• Go first sometimes. Sharing your own answer before asking (“I’ve been thinking about what I’d do differently if I moved again. Have you ever thought about that?”) makes the question feel like an exchange, not a test.
• Give an easy out. “You don’t have to answer that” or “pass if it’s too much” takes the pressure off.
• Follow up gently. “What was that like?” or “How did that change you?” usually gets you further than a new question.
• Don’t fix, just listen. If someone shares something difficult, you don’t need advice ready. “That sounds hard. Thanks for telling me” is enough.

Stage 1: first meetup (light-deep questions)

These are personal enough to be interesting but safe for someone you’ve only just met, whether it’s a first date or a first coffee with a potential friend.

1. What’s something you’re proud of that most people don’t know about?
2. What’s the best decision you’ve made in the last few years?
3. What did you love doing as a kid that you still enjoy?
4. What’s a small thing that instantly makes your day better?
5. What are you looking forward to at the moment?
6. Who has had the biggest influence on the way you see the world?
7. What’s a skill you’d love to master?
8. What would your closest friend say is your best quality?
9. What’s a place that feels like home to you, apart from your actual home?
10. What’s something you used to believe that you’ve changed your mind about?
11. What’s the best piece of advice you’ve ever been given?
12. What does a really good day look like for you?
13. Is there a book, film or song that changed how you think about something?
14. What’s something you’re curious about at the moment?
15. What’s a tradition from your family or hometown you’d like to keep going?
16. What’s one thing you’d like to do more of this year?
17. If you could live anywhere for a year, where would you go and why?
18. What kind of things make you lose track of time?
19. What’s a compliment you’ve received that stuck with you?
20. What’s something that always makes you laugh?
21. What job would you do if money didn’t matter?
22. What’s the most spontaneous thing you’ve ever done?
23. Which friend or family member are you most like?
24. What’s something you’re really good at that surprises people?
25. What’s the most interesting place you’ve ever been?

Stage 2: second and third meetups

Once you’ve met a couple of times and there’s some trust, you can ask about values, turning points and what someone wants from life.

26. What’s a turning point in your life that changed your direction?
27. What are you most grateful for at the moment?
28. What does friendship mean to you? What makes a good friend?
29. What’s something you’ve had to work really hard at?
30. What’s a value you’d never compromise on?
31. When do you feel most like yourself?
32. What’s a risk you’re glad you took?
33. What’s something you wish more people understood about you?
34. What did you learn from your first job?
35. What’s a goal you’re quietly working towards?
36. How do you like to recharge after a hard week?
37. What’s the kindest thing a stranger has ever done for you?
38. Who do you go to when you need advice?
39. What’s a mistake you learnt a lot from?
40. What would you like to be remembered for?
41. What’s something you’ve changed about yourself that you’re proud of?
42. What does home mean to you?
43. Which year of your life would you say was the most important, and why?
44. What’s a belief you hold that most of your friends don’t?
45. What scares you a little but excites you too?
46. What makes you feel appreciated?
47. If you could change one thing about how you grew up, what would it be?
48. What’s the hardest goodbye you’ve had to say?
49. What are you still trying to figure out?
50. How have your priorities changed over the last five years?
51. What does a meaningful life look like to you?
52. What’s something you’ve never told anyone you’d like to try?
53. Who in your life do you wish you’d thanked more?
54. What do you think you’ll care less about in ten years?
55. What’s the best thing about the stage of life you’re in?
56. When was the last time you felt really proud of yourself?
57. What helps you get through difficult times?
58. How do you know when you can trust someone?
59. What does a good weekend with people you love look like?
60. What would you do if you knew you couldn’t fail?

Stage 3: close friends and partners

These are the deepest questions on the list. Save them for people you know well and feel safe with, and make it clear they can pass on anything.

61. What’s something you’ve struggled with that you rarely talk about?
62. When have you felt most alone, and what helped?
63. What do you need from people close to you when things are hard?
64. What’s a regret you’ve made peace with?
65. What did your parents get right, and what would you do differently?
66. What’s the most important lesson a relationship (of any kind) has taught you?
67. What are you most afraid of losing?
68. What part of yourself are you still learning to accept?
69. How do you show people you care about them?
70. What does forgiveness look like to you?
71. What’s a moment that completely changed how you see yourself?
72. What do you think is your biggest blind spot?
73. What would you want to know about your future, if you could know one thing?
74. Is there anything you’ve always wanted to ask me?
75. When did you last cry, and why?
76. What’s a dream you’ve let go of, and how do you feel about it now?
77. What does being a good person mean to you?
78. What part of your life would you like more support with?
79. How do you handle conflict with people you love?
80. What’s something about our friendship (or relationship) you really value?
81. What’s one thing you’d like us to do together in the next year?
82. What’s a version of your life you sometimes imagine?
83. How has your idea of success changed?
84. What would you tell your younger self?
85. What are you proudest of overcoming?

Reflective “what if” questions (any stage)

Hypotheticals are a gentle way to get to deeper answers, because they feel playful even when the answers aren’t.

86. If you could relive one day of your life, which would it be?
87. If you could have dinner with anyone, living or dead, who would you choose?
88. If you had a year off with no money worries, how would you spend it?
89. If you could master one instrument, language or craft overnight, what would it be?
90. If you could ask your future self one question, what would it be?
91. If you had to move to a new country, which would you choose and why?
92. If you could change one thing about the world, what would it be?
93. If you wrote a book about your life so far, what would the chapters be called?
94. If you could keep only three possessions, what would they be?
95. If you could be famous for something, what would you want it to be?
96. If you could solve one problem in your community, which would you pick?
97. If your friends planned your perfect birthday, what would it look like?
98. If you could swap lives with someone for a week, who would it be?
99. If you could give everyone one piece of advice, what would it be?
100. If we met again in five years, what would you hope to tell me?

Questions to avoid early on

Deep doesn’t mean invasive. These are better left until someone chooses to bring them up, or until you know each other well:

• Detailed questions about past relationships or why they ended.
• Questions about money, debt or salary.
• Health conditions, mental health history or family trauma.
• “Where do you see this going?” on a first or second date.
• Anything that sounds like a test (“What’s your worst trait?”).
• Questions about their body, weight or appearance.

If someone does share something personal, that’s a gift. Thank them, don’t push for more, and don’t share it with anyone else.

What about the “36 questions” study?

You may have heard of the “36 questions to fall in love”. They come from a 1997 study by psychologist Arthur Aron and colleagues, published in Personality and Social Psychology Bulletin. Pairs of strangers took turns asking each other 36 questions in three sets of 12, which became more personal as they went on, spending roughly 15 minutes on each set. Pairs who worked through the closeness questions reported feeling closer to each other than pairs who made small talk.

Two things worth knowing: the study was about creating closeness between strangers in a lab, not a guarantee of romance, and the authors themselves noted it was unlikely to produce the commitment or loyalty that take longer to build. The underlying idea is still useful in everyday life, for friends as much as dates: gradual, mutual self-disclosure (you share a bit, they share a bit, and it slowly goes deeper) is how closeness tends to grow.

A worked example: going one step deeper

Here’s how a light question can turn into a meaningful conversation at a second meetup, without anyone feeling put on the spot.

Maya: What are you looking forward to at the moment?

Tom: Honestly, my sister’s moving back from Melbourne next month. I haven’t lived in the same country as her for six years.

Maya: Oh, that’s huge. What’s that been like, having her so far away?

Tom: Harder than I expected. We’re close, but the time difference meant we mostly sent voice notes.

Maya: I get that. My best friend moved to Dublin and it took us ages to work out how to stay close. What do you think you’ve missed most?

Tom: Just the boring stuff, really. Popping round. Having someone who remembers everything about you.

Maya: That’s a lovely way to put it. Is that what makes a good friend, for you? Someone who remembers?

Maya never asked a “heavy” question out of the blue. She started light, followed up with genuine interest, shared something of her own, and only then asked a values question that grew naturally from what Tom had said.

Deep questions for friends vs dates

Nearly every question here works for both. A few tips:

• With a new friend, focus on interests, values, friendships and what they want from the place they live. Questions like “What does friendship mean to you?” are a great signal that you’d like to be friends.
• With a date, the same questions work, but skip anything that sounds like you’re assessing them as a long-term partner on the first meeting.
• In a group, stick to the “what if” questions. They let several people answer without anyone having to share something private in front of others.

A note on comfort and safety

Deep conversations happen most easily when both people feel relaxed, so it’s worth getting the basics right for early meetups: a public place, a friend who knows where you are, and your own way home. Our guides to first date safety tips and meeting someone from the internet safely cover the essentials. And be wary of anyone who pushes for very personal details (where you live, your finances, your past) far faster than you’re comfortable with. Depth should be mutual and gradual.

Turning good conversations into regular plans

The best deep conversations usually happen on the third or fourth meetup, not the first. That means the real skill is making sure there is a third or fourth: suggesting the next plan before you say goodbye, keeping it low-key (a walk, a coffee, a quiz night) and following through. MeetNow, our own app (see our disclosure), is built around exactly that kind of plan.

Want to turn this into an actual plan? MeetNow is a free app for meeting people in person: a host posts a plan at a public place, says who pays (host pays, split, pay your own or free) and picks who joins. It is live on the web now, starting in Malta, with the phone apps on the way: open MeetNow and see the plans near you.

FAQ

What are good deep questions to get to know someone?

Open questions about experiences and values, such as “What’s a turning point that changed your direction?”, “When do you feel most like yourself?” or “What does friendship mean to you?” Match the depth to how well you know each other.

How do you ask deep questions without being awkward?

Start with lighter conversation, share your own answer first sometimes, give people an easy way to pass, and follow up on what they say rather than jumping to a new heavy question.

Are deep questions okay on a first date?

Light-deep questions are, such as “What are you proud of?” or “What’s the best advice you’ve been given?” Save questions about past relationships, trauma, health or money for later, or for when the other person brings them up.

Do the 36 questions really make people fall in love?

Not exactly. The 1997 study by Arthur Aron and colleagues found that pairs of strangers who asked each other increasingly personal questions felt closer than pairs who made small talk. It showed how closeness can grow through mutual sharing, not that it guarantees romance.

What questions should you avoid asking someone new?

Detailed questions about exes, money, health or family trauma, anything about their body or appearance, and questions that feel like a test of their character or suitability as a partner.