60 Deep Questions to Ask Someone to Strengthen Your Bond

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Questions to Get to Know Someone Better and Build a Stronger Connection

Deep Questions to Ask Feature image man and woman smiling behind books

Perhaps you just met someone whom you’d like to know on a deeper level. Or maybe you’ve been with someone for a while and you want to strengthen your bond even further. Whatever stage you are in your relationship, these questions will help you discover new things about each other and build a stronger connection.


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Deep Questions to Ask Someone When You’re Just Getting to Know Them


Deep Questions to Ask Pinterest image woman sitting alone in a restaurant


1. What makes you laugh?

2. How important is work-life balance to you?

3. If money isn’t an issue, what would you do for a career?

4. What’s your relationship like with your parents?

5. What’s your favourite film/book, and what do you like about it?

6. How do you usually respond to criticism?

7. What frustrates you?

8. What’s your motto in life?

9. Who do you look up to?

10. How do you deal with setbacks?

11. What does “success” mean to you?

12. What moves you?

13. What qualities do you value in a true friend?

14. What’s the best thing you remember from your childhood?

15. How do you deal with disagreements and conflicts?

16. What’s one thing you want to improve about yourself?

17. What’s something that you like to do, but suck at?

18. What’s something you know it’s bad for you, but have a hard time giving up?

19. Do you consider yourself a curious person? Why or why not?

20. What three words would you use to describe yourself?

21. What are some common misconceptions people have about you?

22. What’s your definition of a good life?

23. If you have the whole day to yourself, what would you do?

24. How do you cope with stress?



Deep Questions to Ask Someone to Further Strengthen Your Bond


Deep Questions to Ask Pinterest image man looking back at a smiling woman


25. When you think of the word “home”, what images come to mind?

26. What’s your biggest fear in life?

27. What do you think is life’s purpose?

28. Who made the most impact on you when you were growing up?

29. How do you show someone you love them?


30. What makes you feel loved and appreciated?

31. If you could go back in time and meet yourself from 10 years ago, what life lessons would you share with your younger self?

32. When was the last time you had to make a hard decision, and how did you make your decision in the end?

33. What’s the biggest challenge in your life right now?

34. What was the scariest moment in your life so far?

35. How much control do you feel you have over your life?

36. What’s something you wish you had done differently?

37. What kinds of compliments do you like to hear the most?

38. What’s an opportunity you feel you missed?

39. How have you changed in the past decade?

40. When was the last time you cried?


41. What’s the most beautiful thing in the world you can think of?

42. What’s an irrational thought that crossed your mind lately?

43. What would you do if you only had one month to live?

44. When was the last time you felt envious or jealous of someone?

45. How satisfied are you with your life right now?



Fun Deep Questions to Ask Someone to Get to Know Them Better


Deep Questions to Ask Pinterest image man and woman holding a sparkler


46. What superpower do you want to possess the most?

47. What’s the craziest thing you’ve ever done?

48. If you could have only one kind of food for the rest of your life, what would it be?

49. If you were given the ability to travel in time, would you go back to the past or go forward to the future, and why?

50. If you can take only one thing with you on a vacation besides your wallet and phone, what would it be?

51. What’s your favourite spot in your house?

52. What’s on your shopping list right now?

53. What’s the one thing you regret buying the most?

54. If you were to write a book, what would it be about?

55. Who’s your favourite TV show/movie character and why?

56. If you won a million dollars, how would you spend it?

57. How would you survive an apocalypse?

58. If you could change one thing that happened in world history, what would it be?

59. If you could go anywhere in the universe, where would it be?

60. What’s your spirit animal?


Now remember, asking these deep questions is just one part of the equation. If you want to truly understand someone and deepen your bond, there are a few things you have to be mindful of.

Read on to find out what they are.  But first, I put together a list of 21 questions that will deepen your bond which you can print out and share with your partner. Download your free copy now, and bring it to your next date night!

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Things to Remember If You Want to Get to Know Someone Better And Deepen Your Bond


1. Be Authentic

You can ask all the best questions in the world, but if you can’t get people to open up and answer them candidly, you won’t get anywhere close to a real connection.

If you want someone to open up to you, first you have to get them to trust you. And how can you establish trust with someone you don’t know well in a relatively short amount of time?

Be authentic.

Authenticity is widely known, in the business world, as one of the key qualities a good leader should possess—and for a good reason. It shows you’re willing to show the world who you are in the truest light—both the good and bad. And that makes you instantly more relatable and trustworthy.

So don’t be afraid to show your real self—flaws and all.


man carrying woman on his back having fun


2. Show Genuine Interest

Would you want to get closer to somebody who keeps cutting you off, checks their phone every few minutes, or gives you a blank look until the topic changes to something they love to talk about?

Probably not.

We’re drawn to people who show genuine interest in what we say or do. Sure, some people might like “hard to get”, but studies show that people tend to like those who actually take an interest in them. It’s called “reciprocal liking”—we like those who like us, it’s as simple as that.

How do you show genuine interest? Besides giving them your full attention, try to maintain good eye contact and ask follow up questions such as “can you tell me more about that?”


3. Respect Their Values

The foundation of a healthy relationship is built on mutual respect. If you want to develop and maintain a deep bond with someone, you have to show respect for their values, even if you don’t necessarily agree with them.

If you’re just getting to know someone, here’s a tip to help you establish a deeper, more meaningful connection right away:

First, listen for values-related content in what they say. For example, if they say they have two dogs and a cat with enthusiasm, then it’s obvious they love animals. Then make a point to acknowledge their values by saying: “Sounds like taking care of animals is something you enjoy and value, tell me more about that.”

And watch their face light up.


woman and man standing in front of black and white background


4. Listen to Understand

How often do you listen to understand? I mean, really LISTEN to understand the other person’s feelings, desires, hopes, and dreams? I know if I’m truly honest with myself, a lot of times instead of listening to understand, I’m listening to respond.

What’s the difference, you ask?

Well, when you’re listening to respond, your mind is occupied by your own thoughts, emotions, or even ideas of what you want to say next. Often, you’re so eager to express them that you start to jump in before the other person can finish their sentence.

But when you’re listening to understand, you’re making a conscious effort to not only focus your entire attention on the other person, but to also put yourself in their shoes. And most importantly, you’re deeply curious about their thoughts and feelings. Instead of interrupting, you give them enough space to fully express themselves. You dig deeper into what they’re saying by asking follow-up questions. You tell them with your body language that you crave to know more.

And this is exactly the type of listening that we need to practice more of in all of our relationships.


5. Show Gratitude

If you want to build a deeper bond with someone, show them, with action, that you’re grateful to have them in your life.

Research shows that gratitude can help bring two people closer in a relationship. One study found that couples who expressed gratitude for one another not only had more positive feelings towards each other, but they were also more open to discussing problems in the relationship with one another.

Besides saying “thank you”, there are many ways to show gratitude in a relationship. For example, take the time to learn more about something they’re passionate about, or support them in the pursuit of their personal goals and dreams. Remember, when it comes to showing gratitude, there could be hundreds, even thousands of different ways, but the key is to make the other person feel appreciated in a way that they understand and value.


man and woman lying down and looking at each other


Now that you have everything you need to get to know someone and deepen your relationship, it’s time to turn knowledge into practice! But before you go, I have one last question for you:

Which question did you like the most?

Tell me in the comments below!

And don’t forget to grab your copy of “21 Questions to Deepen Your Bond”!

Get More Out of The Budding Optimist Blog!

Subscribe to The Budding Optimist Newsletter to receive more tips to help you live a heathier and happier life, plus the latest blog updates, bonus content, and more! Don't worry, I won't spam you, 1-2 emails a month at the most!

You can unsubscribe at any time.

By signing up, you're giving consent to use this information to send emails and communications as described in the site's Privacy Policy.


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120 Questions to Ask Yourself for Deep Self-Discovery

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How to Stop Taking Things So Personally

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