It’s natural and healthy to want to get to know the people around you better. But, it can feel awkward or uncomfortable to start those conversations. You may feel you don’t know where to start or what questions to ask. 

On the other hand, you may wish to deepen your relationship with those you already know well. Even the people we know best, such as our spouse, family members, or best friends, can surprise us with new information. 

Whether you’re looking for icebreaker questions to start a conversation, or deep and personal questions to foster emotional intimacy, below you’ll find a variety of questions to get to know someone better. These questions are perfect for first dates, getting to know a coworker better, strengthening a friendship, or even creating conversation in a long-term partnership. 

Benefits of Asking Questions to Get to Know Someone 

By asking meaningful questions to get to know someone better, you can foster a deeper connection with them. These questions will allow you to hear their inner thoughts, emotions, and beliefs, helping to strengthen your relationship and learn more about each other. 

When you create a space to hear another’s perspective, you develop emotional intimacy through vulnerability. Being vulnerable can feel scary or uncomfortable, but in a safe space, it can help ease social anxiety, strengthen relationship bonds, and increase self-awareness. 

When you ask these questions, expect to have a turn answering them. Not only do you have an opportunity to share your thoughts, but this also helps create a feeling of shared vulnerability. When both people feel heard and seen, this fosters a sense of safety and trust in the relationship. Safety and trust are key to building long-lasting, healthy relationships. 

For new relationships, this list of questions is a great way to know whether or not you align in values, beliefs, and future goals. As such, they are perfect for those wanting to deepen a romantic relationship or friendship and are curious about where the relationship is heading. 

Creating A Safe Space for Deep Questions 

Because some of these questions to get to know someone can feel personal and vulnerable, it’s important to create a safe space for both of you to share your thoughts and feelings. 

One way to create a safe space to ask deep questions is to use a shared journaling app like Waffle. What is shared journaling you might wonder? It's a personal journal that two or more people use that allows them to share their thoughts, feelings, and emotions. It’s a wonderful way for long-distance friends, couples, and family members to communicate and improve their relationships. 

On the Waffle app, you can ask meaningful questions to get to know the people you love most, but in a safe space that allows them to answer in their free time. 

For example, Heidi uses Waffle with her teenage daughter and says,

This app has allowed us to talk about things that are not easy to talk about in person and to discuss the things that really matter to us in a non-confrontational way.

Tips for Asking Questions to Get to Know Someone

Whether you’re asking questions to get to know someone in person or on the Waffle app, approach the conversation with openness and curiosity. Practice active listening, which involves being fully present to what the other person is sharing. 

Don’t be afraid to ask follow-up questions. While talking pay attention to your emotional responses and body language. If you notice tension building within yourself or the other person, take a pause. Or if it feels right, be honest with how you feel and explore where the tension lies. This will create even more safety and vulnerability, which will help strengthen the relationship. 

Light-hearted Conversation Starters to Break the Ice 

These light-hearted questions to get to know someone are perfect for first dates or talking with someone new. They are fun and easy to answer, making them great icebreakers before you head to deeper waters. 

1. How would you spend 1 billion dollars? 

2. What’s your favorite movie or book genre? 

3. What’s your favorite book and why? 

4. If you had a day to do anything you wanted without worrying about money or responsibilities, what would you do?

5. Would you rather spend the day in the mountains or at the beach and why? 

6. What was the most delicious meal you’ve ever had? 

7. Where’s the most beautiful place you’ve traveled to? 

8. What’s your favorite way to spend the weekend? 

9. If you had any superpower, what would it be and why? 

10. What’s your comfort TV show? 

11. Are you an introvert or an extrovert? 

12. What’s your favorite type of music? 

13. What are some of your hobbies or interests? 

14. What is your favorite season and why? 

15. What’s your favorite form of exercise? 

16. If you could be any animal, what would you be? 

17. What’s your favorite holiday and why? 

Deep Questions to Get to Know Someone

It’s time to get personal - these questions will allow you to explore the depths of the other person you may not have known before. These deep questions will foster emotional intimacy and vulnerability. They are perfect for close friends, couples, and family members. 

18. What are you passionate about? 

19. What do you wish more people knew or recognized about you? 

20. What are you most grateful for in your life? 

21. What values do you look for in a romantic partner or friend? 

22. Do you believe in a “higher power?” If so, what does that mean to you? 

23. When or where do you feel most yourself? 

24. What are some ways you’ve grown in the past year? 

25. Do you feel comfortable in social situations? Why or why not? 

26. How do you take care of yourself when you feel anxious or stressed? 

27. What are your biggest pet peeves? 

28. What are your creative gifts? 

29. Who are you closest to in your family? 

30. What brings you joy? 

31. What are your self-care habits? 

32. Who do you look up to? 

33. What is a challenge you’ve overcome? 

34. What’s your biggest fear? 

35. What are some of your strengths? 

36. What are some of your weaknesses? 

Waffle provides daily questions like the deep questions listed above. If you feel uncomfortable asking these questions in person, consider asking them in a safe space like the Waffle app. 

Justeen uses the app with her long-distance boyfriend and says,

My boyfriend and I are closer by using Waffle and it lets us get to know each other better due to the prompts that ask questions that we wouldn’t even think to ask each other. … I get to know the inner workings of his brain due to the thought-provoking questions as well as wake up to cute messages. It has let us become closer as partners and I’m grateful for this app.

Interesting Questions to Get to Know Someone 

These questions aren’t your average get-to-know-someone questions. They are a bit “out there” and will cause the person to think outside the box. They are deep and quirky and will lead to fascinating conversations. Try these interesting questions with your friends, coworkers, family members, or if you're brave, on a first date. 

37. Have you ever had any supernatural experiences? 

38. What is one of the most impactful books you’ve ever read? Why was it impactful? 

39. What do you feel like you came into this life to do or experience? 

40. What is the most impactful travel experience you’ve had? 

41. What is the weirdest thing you’ve ever experienced?  

42. Do you enjoy being alone? 

43. How do you spend your alone time? 

44. Do you like to explore the meaning of your dreams? 

45. What was one of the most vivid or significant night-time dreams you’ve had? 

46. Do you feel connected to your intuition or emotions? 

47. Do you believe in aliens? 

48. When was the last time you felt full of joy? 

49. Do you believe in past lives? Why or why not?

50. What makes you feel most alive? 

51. What element do you resonate with most? Air, fire, water, or earth? 

52. Does your career align with who you are on a deeper level? 

53. Do you believe everything happens for a reason? 

54. Do you feel connected to your ancestors? 

Questions to Get to Know Someone’s Past 

We can learn much about who a person is through their past experiences. Our past shapes who we are today, and our childhood experiences impact the rest of our lives. As such, understanding someone’s past is key to knowing them on a deeper level. These are good questions to ask your partner, best friends, grandparents, or parents. 

55. What was your childhood like? 

56. What is something your parents taught you that you are grateful for and has helped you out in life? 

57. Are you close with your family or parents? 

58. What is one of your favorite childhood memories? 

59. What was your first job? Did you enjoy it? 

60. What was your high school experience like? 

61. What lessons did you learn from your first serious relationship? 

62. What is a past accomplishment you’re proud of? 

63. Who was your first true love? 

64. When you were a kid, what did you want to be when you grew up? 

65. Did you have any natural talents or gifts as a child? 

66. Are there any traits you had as a child you feel that you lost that you want to reclaim?

67. How have your past experiences shaped who you are today? 

68. What do you wish you could tell your teenage self? 

69. Do you have a favorite family tradition?  

Asking about someone’s past can bring up challenging emotions or hard conversations. It can also take time for a person to think about their past, so they might not answer right away. As such, consider asking questions about someone’s past in a safe, gentle, and patient way. 

Waffle is an easy way to ask questions about someone’s past, allowing the other person time to process the question and respond thoughtfully. 

For example, Joseph uses the app with his girlfriend and shares,

It's given us a way to share about hard topics in a safe space. … We are both divorced and have kids so there are lots of different aspects to blending a family together. We also have different parts of our own stories that we are trying to work through. This has really given us a way to be vulnerable and break old habits.

Questions to Get to Know Someone’s Future Goals and Dreams 

We all have visions for the future, goals we want to meet, and ideas about our future selves. Asking questions to get to know someone’s future will help you learn more about what they desire for their life and who they want to become. 

70. What is your dream job? 

71. What does your dream house or property look like? 

72. Do you want children? 

73. What goals or projects are you working towards? 

74. Where would you love to travel to? 

75. What are your career goals? 

76. Where do you see yourself in five years? 

77. What do you hope our future society looks like? 

78. What is a skill or hobby you would like to learn? 

79. Do you have anything planned for the upcoming future that you’re looking forward to? 

80. What do you see when you envision your future self? What accomplishments have they made? 

81. How is your future self different from who you are at this moment? 

82. Is there anything you’re trying to manifest? 

Questions to Get to Know Someone’s Romantic Life 

These are questions to ask your romantic partner or to get to know a friend's love life. They can help offer clarity about romantic values, expectations, and what the future holds. 

83. What’s your favorite thing about your (or our) relationship? 

84. How do you feel about marriage? 

85. What is your love language? 

86. What do you look for in a life partner? 

87. What are your relationship deal breakers? 

88. How do you feel about open relationships? 

89. Do you fall in love easily? 

90. How do you handle arguments or challenges in your relationship? 

91. What do you deeply long for in a relationship? 

92. In what ways does your partner (or I) make you feel seen or loved?

93. What is something you wish to improve in your (or our) relationship? 

94. What is your favorite thing to do with your partner (or me)? 

95. Do you believe in soulmates? Why or why not?

Communicating with your romantic partner about their relationship goals and expectations can help you grow closer. But asking these questions isn’t always easy or comfortable. When asking questions in a shared journal like the Waffle app, you can ease some of the discomfort and fear that comes with talking about your relationship. 

Scott shares,

I use Waffle with my girlfriend and we use it to communicate in a safe place the important and difficult topics in our relationship. It has helped us both to identify and express our issues from previous toxic relationships we were in and trauma triggers as well. In doing so we have begun to fix those scars and really make positive changes together. I think it has been an amazing experience and something we are going to continue using for a long time.

Ask Questions to Get To Know Someone to Create a Lasting Bond

Now that you’ve read through the best questions to get to know someone, you won’t have to worry about awkward pauses or how to start a conversation. Whether you want to meet new people or deepen existing relationships, these questions will help you create meaningful conversations and lasting bonds. 

If you’re ready to strengthen your relationships through more intimate conversations, consider downloading the Waffle app and sharing it with your loved ones. 

Waffle user Evan uses the app with their siblings and partner, saying,

Waffle has really helped us form deeper connections. I've been able to tell my siblings my struggles and learn theirs and I've been able to form deeper connections with my partner by answering the daily questions or creating our own entries.

In this way, you can create multiple journals for each relationship you want to nourish. With the daily question prompts, you’ll never run out of things to talk about. Download Waffle and start meaningful conversations with your loved ones today.