50 Questions to Ask to Get to Know Someone (Without Awkward Small Talk)
Small talk has its place, but let’s be honest—it gets old fast. You’re sitting across from someone you actually want to know, and suddenly you’re stuck in that loop of “So, what do you do?” and “How’s work?” and “Crazy weather, right?” It’s safe, but it doesn’t really tell you who they are.
Real connection usually lives a little deeper than that. It’s in the stories they tell, the way their eyes light up when they talk about something they care about, and the tiny details that don’t usually come up in small talk. The right questions can gently move you past the surface without turning the conversation into a therapy session or a job interview.
These 50 questions to ask to get to know someone are meant to be soft, human, and easy to sprinkle into real conversations—on dates, with new friends, or even with people you’ve known for years but want to feel closer to.
How to Use These Questions (Without Making It Weird)
You don’t have to sit there and read these questions off like a checklist. Think of them more like a little menu you can keep in the back of your mind (or your Notes app). Pick one or two that fit the moment and the level of trust you already have with the person. Start lighter, and only move deeper if the conversation feels safe and mutual.
Also: answer some of these yourself. Real connection is a two-way street, not an interrogation. If you ask them about their fears or dreams, share yours back. You’ll usually get more honest, thoughtful answers if you’re willing to be a bit open too.
Alright, let’s get into the questions.
Light, Low-Pressure Questions to Open Things Up
These are easy, non-intense questions to ask to get to know someone without feeling like you’re suddenly doing a life audit.
1. What does a perfect slow day off look like for you?
This tells you a lot about their energy, priorities, and what “rest” means to them.
2. Are you more of a morning person, night owl, or “depends on the week” person?
Great for laughing about chaos, routines, and real life.
3. What’s your go-to comfort show or movie when you’ve had a long day?
Instant doorway into nostalgia, taste, and what makes them feel safe.
4. What’s a little thing that never fails to put you in a better mood?
You’ll learn what lifts them up—and maybe file it away for later.
5. What kind of music have you been into lately? Any repeat songs?
Super casual, but can turn into a whole conversation about feelings and memories.
6. Are you more of a planner or a “let’s see what happens” person?
This hints at how they move through life… and how they might handle change.
7. What’s your favorite way to spend time alone?
You get insight into how they recharge when no one else is watching.
8. Do you have any silly little routines or habits that make your day feel better?
Invites them to share quirks—those are often the cutest parts.
9. What’s something small you’re really into right now—like a snack, show, hobby, or app?
Shows you what’s currently lighting them up, even if it’s simple.
10. If you could instantly teleport anywhere for a weekend, where would you go and what would you do?
Light, imaginative, and secretly revealing about their idea of joy.
Questions for When You Want to Get a Bit Deeper
These questions are still gentle, but they start touching on feelings, values, and those “oh, you really get me” moments.
11. What’s something you’ve learned about yourself in the past year?
Invites reflection without demanding oversharing.
12. When do you feel most like yourself?
Their answer often points to the environments and people where they feel safe.
13. What’s a belief or mindset you’ve outgrown that you’re proud of letting go of?
This shows growth, self-awareness, and how they handle change.
14. What’s one thing you’re working on healing or improving in yourself right now?
Deep—but you can answer it too, so it feels balanced.
15. What kind of friend or partner do you try to be for the people you love?
Reveals their relationship values and emotional style.
16. What’s something you wish people understood about you more clearly?
Gives them a chance to share a side that’s often missed.
17. What’s a small decision you made that ended up changing a lot for you?
You’ll usually get a story that shows how they think and choose.
18. When you’re really stressed, what actually helps you calm down?
This quietly tells you how to support them, too.
19. What does “feeling safe” in a relationship or friendship look like for you?
A gentle way of asking about their needs—emotional, practical, or physical.
20. What’s something you’re quietly proud of that you don’t talk about often?
Helps them open up about strengths they usually downplay.
Questions to Ask on Dates (Without Making It an Interview)
If you’re dating, these questions to ask to get to know someone help you move past “What do you do?” and into “Who are you really?” And as you’re getting to know someone new, it helps to know what healthy love even looks like—these relationship green flags that actually make love last give you a calm checklist to keep in the back of your mind.
21. What kind of moments make you think, “Oh wow, I really like my life right now”?
Shows you what contentment looks like for them.
22. When you think about the future, what feels exciting—not just impressive?
Distinguishes between what they truly want and what sounds good on paper.
23. What’s your love language—or, if you don’t know, how do you naturally show people you care?
Great entry point into emotional needs without sounding clinical.
24. What’s your favorite kind of date or hangout—chill at home, going out, little adventures?
Helps you see if your “fun” matches theirs.
25. Are you more likely to text first, call randomly, or show up with snacks?
A playful way to talk about communication styles.
26. What’s one green flag you really appreciate in other people?
Their answer often hints at how they want to be treated too.
27. Is there a lesson from a past relationship or friendship you’re grateful you learned?
Lets them share history without turning it into an ex-rant.
28. How do you like to handle conflict or misunderstandings when they come up?
Huge insight into emotional maturity.
29. What makes you feel genuinely appreciated in a relationship?
Opens the door to expectations in a soft way.
30. What kind of partnership or friendship energy are you working toward these days?
Invites them to name the kind of dynamic they’re hoping to build.
Questions to Get Closer to Friends (Old or New)
These work beautifully with people you already know, but want to know better—friends, coworkers, even family.
31. What’s something you’re really looking forward to in the next few months?
Future-focused, but still warm and personal.
32. What’s a core memory from your childhood that still makes you smile?
Gives you a sweet glimpse into their past.
33. What’s something you’ve gone through that changed how you see the world—for better or worse?
Can get deep, so match your own vulnerability.
34. How do you like people to show up for you when you’re going through a rough time?
Good to know if you want to be a better friend to them.
35. What kind of friend do you hope you are to people?
Helps them share their intentions, even if they’re still learning.
36. What’s a dream or goal you don’t talk about a lot, but still quietly hope happens one day?
Lets you cheer them on in a more meaningful way.
37. If we had a tradition together—like a monthly thing we always do—what would you want it to be?
Playful, and might give you an idea for an actual plan.
38. What are you unlearning about relationships or friendships right now?
Shows you where they’re growing and shifting.
39. What’s something you wish more people asked you about?
Then, you get to be the one who asks.
40. What kind of people do you feel most at home with?
Reveals what makes them feel seen and accepted.
Cozy Late-Night or Text Conversation Questions
These are perfect for voice notes, long chats, or those “we’re both still awake, so let’s talk” nights.
41. What’s something that’s been on your mind a lot lately, in a good way or a confusing way?
Gives them room to vent or share excitement.
42. What’s a risk you’re glad you took—even if it scared you at the time?
Always comes with a story.
43. If you could send one message back in time to your younger self, what would you say?
Opens the door to vulnerable, meaningful reflection.
44. What do you think you’re underrated at, as a person?
A soft way to ask about strengths and hidden talents.
45. What does “home” mean to you, beyond just a place?
Can get beautifully emotional and layered.
46. When do you feel the most calm and okay in your body?
Brings in nervous system and safety without sounding clinical.
47. What’s a small moment from this past year that you don’t want to forget?
Helps them pull up something tender and important.
48. What are you learning to forgive yourself for right now?
Very deep—so you’ll want to share your own answer too.
49. What do you hope people quietly think or feel after spending time with you?
Their answer says so much about their heart.
50. If we’re still in touch a year from now, what do you hope we’re looking back and laughing or smiling about?
Future + connection + a bit of softness, all in one question.
A Quick Note If You’re Shy, Socially Anxious, or Overthinking It
If you’re reading all of this and thinking, “I could never just ask someone that,” breathe. You don’t have to transform into the world’s smoothest conversationalist overnight. You can ease in—maybe save just three or four of these questions to your phone and test them out with someone you already feel relatively safe with.
Remember: most people are actually craving deeper, more honest conversations. They’re just waiting for someone else to go first.
And if part of your hesitation comes from past experiences where someone made you feel like you were in competition with their past, this breakdown of clear signs he’s comparing you to his ex might help you trust your gut sooner next time.
