Questions to Ask to Get to Know Someone, From Easy to Deep

What are good questions to get to know someone?

Good questions are open, specific and easy to answer on the spot. "What have you been enjoying lately?" works better than "What are your hobbies?", because it sounds like a chat and not a form. Start with a question that fits how well you know the person, then let their answer pick the next one.

Jastado is being built around questions like these: money, family, lifestyle, values and long-term goals. If that's the kind of dating you want, join the waitlist for your city.

Why the right questions bring people closer

Researchers have tested this. In a 1997 study, Arthur Aron and colleagues paired strangers for 45 minutes of questions that slowly got more personal. Those pairs felt closer afterwards than pairs who spent the same time on small talk.

Asking also makes you more likable. A 2017 Harvard study of live conversations found that people who asked more questions, especially follow-up questions, were liked more by their partners. In the speed-dating part of that study, people who asked more follow-ups were more likely to get a yes for a second date.

Most of us also hold back for no good reason. In a 2022 set of experiments, people expected deep talks with strangers to be more awkward than they really were. The deep talks left them feeling more connected than the shallow ones did.

So the lesson is simple: ask, go one step deeper than feels comfortable, and follow up on what you hear.

Easy questions to start with

These work on a first date, at a party or with a new coworker. Still planning where to meet? Our first date ideas make the talk easier. They are easy to answer and still tell you something real.

1. What did you do this week that you actually enjoyed?
2. What's a perfect Saturday for you?
3. What are you into right now that you could talk about for an hour?
4. What's the best thing you ate recently?
5. Where did you grow up, and what was it like?
6. What's a small thing that always makes your day better?
7. What's something you're looking forward to?
8. Are you a morning person or a night person, honestly?
9. What's the last thing you learned just because you were curious?
10. What do your friends come to you for?

Questions about daily life

Daily habits shape a shared life more than big dreams do. These questions show how someone spends their time and energy.

11. What does a normal weekday look like for you?
12. How do you like to recharge after a long week?
13. Do you plan your weekends, or see what happens?
14. What's one routine you never skip?
15. How tidy are you, really, on a scale from one to ten?
16. Do you like a full calendar or lots of free time?
17. What's your favorite way to spend an evening at home?
18. How much time do you like to spend alone?
19. What's a chore you don't mind and one you avoid?
20. If you had an extra free hour every day, what would you do with it?

Questions about values

Values decide what someone does when life gets hard. Ask these once you've moved past small talk. For each heavy one, there's a lighter one you can use first.

21. Light: What's a cause or topic you'd happily argue about at dinner?
22. Deep: What do you believe that most people around you don't?
23. Light: Who's someone you really admire, and why?
24. Deep: What's a mistake that taught you something you still use?
25. Light: What makes a person a good friend in your eyes?
26. Deep: When have you been proud of a hard choice you made?
27. What does honesty mean to you in a relationship?
28. How do you like to handle disagreements?
29. What do you need from people when you're stressed?
30. What's one thing you'd never compromise on?

How someone handles closeness and conflict is also a pattern worth noticing over time. Secure attachment style explains what the research says about it.

Questions about money

Money is a topic many new couples skip. You don't need a budget talk on date three, but how someone thinks about money says a lot.

31. What's something you'd happily spend too much on?
32. What's something you refuse to pay for?
33. Are you more of a saver or a spender?
34. What did your family teach you about money, on purpose or not?
35. What's a purchase that made your life better?
36. Would you rather have more money or more free time?
37. How do you feel about splitting costs in a relationship?
38. Is there a money goal you're working toward right now?

Questions about family and friends

The people someone grew up with often shape what they expect from a partner. Go gently here, because family can be a painful topic for some.

39. Who in your family are you most like?
40. What was a family tradition you loved as a kid?
41. How often do you see your family now, and is that the right amount for you?
42. What's something your family does that you want to keep doing?
43. What's something you want to do differently from how you grew up?
44. Who are the friends you'd call at 2 a.m.?
45. How do you feel about pets?
46. How do you picture holidays: big family gatherings or something quiet?

Questions about the future

These questions show whether you want the same kind of life. They matter most once you're dating and want to know where it could go.

47. Where do you see yourself living in five years?
48. Is there a city or country you'd love to try living in?
49. How important is your career to you compared with the rest of your life?
50. Do you want kids someday, or is that not for you?
51. What does a good life look like to you at 70?
52. What's one thing you want to do before you turn 40, or the next big birthday?
53. How do you feel about marriage?
54. What's a dream you've kept quiet about?

Fun questions for any moment

Not every question has to be serious. These keep the mood light and still show how someone thinks.

55. What's a hill you'll die on that doesn't matter at all?
56. What's the most "you" thing you own?
57. Which fictional world would you live in?
58. What's a song you'll never skip?
59. What's the strangest job you've ever had?
60. If you could master one skill overnight, what would it be?
61. What's a food you loved as a kid and still secretly love?
62. What's the best trip you've taken, and what made it great?
63. What would your perfect day off look like, from start to finish?
64. What's something you're weirdly good at?
65. What's the last thing that made you laugh out loud?
66. Cats, dogs, or neither?
67. What's a movie you could watch again tonight?
68. What's a small risk you're glad you took?
69. What's something on your "someday" list?
70. What question do you wish people asked you more often?

How to ask follow-up questions

The list gets the talk started. The follow-up is where you actually get to know someone.

• Pick one detail from their answer and ask about it: "You said you hate planning weekends. What happened the last time you tried?"
• Ask how it felt, not only what happened: "What was that like for you?"
• Ask why it matters: "Why is that the one routine you never skip?"
• Share your own answer too, so it feels like a talk and not an interview.
• Match their depth: a one-line answer means stay light for now; a long, open one means you can go a step further.
• Let silence sit for a second; people often add the most interesting part after a pause.

If you want more ideas, you can also send us the question you wish people asked. Meeting someone from a dating app for the first time? Our trust and safety page has practical steps. Already dating someone? Try our questions to ask your girlfriend, sorted by how long you've been together. Meeting a man and unsure what to ask? Try our questions to ask a guy, split by just met, texting and getting closer. Have your eye on someone you have not dated yet? Start with our questions to ask your crush, which are light enough for a first chat or a text.

Summary

Start light, listen, follow up, and answer each question yourself before you move on. Not sure what you want from a partner yet? Our guide to relationship deal breakers helps you name it.

For more, read questions to ask your boyfriend, the stage-by-stage questions to ask your girlfriend, and first date ideas for where to meet.