Are you nervous about talking to your crush or making a good impression?

Maybe you have pre-date jitters, don’t worry we’ve all been there and it’s completely normal.

These questions to ask your crush are also icebreakers that can be used on anyone.

Just so you’re prepared in any social situation, it’s good to have some of these handy as your go to conversation starters that go beyond, so what do you do? Or so tell me about yourself?

Yawn!

God knows I hate that question and something tells me I’m not the only one.

Don’t worry babe, I’ve got you!

These questions to ask your crush, will have you feeling like a social butterfly and a flirt all wrapped up in one and by the time we’re through, you will have the confidence to talk to anyone!

And the best part?

These are not too intense, dramatic, or heavy.

Although, to avoid sounding like his therapist, you don’t need to jump straight into asking your crush deep questions instead, you can ease in with stories and what he shares about himself.

Experiences

When it comes to questions to ask your crush, experiences are where things start to feel real.

Anyone can answer surface-level stuff. Favorite color. Favorite food. Basic small talk.

But when you start asking questions to your crush about their life experiences, you’re discovering who they’ve been.

Experiences reveal how they handle challenges, what makes them laugh, what shaped them, what they value without even realizing it.

QUESTIONS TO ASK YOUR CRUSH

1. Is there something you tried on a whim that turned out way better than expected?

2. Do you remember a day that started normal and ended up being surprisingly great?

3. Where’s a place you’ve been that you’d go back to without thinking twice?

4. Has anything ever made you laugh way harder than you expected?

5. Did you ever discover you were good at something totally by accident?

6. What usually puts you in a good mood almost instantly?

7. How did you end up getting into one of your current interests?

8. When do you feel most like yourself?

9. Is there a memory that just feels very you?

10. Have you ever had a moment where you thought, “okay, life’s actually kind of nice”?

11. What’s a small win from your past that still feels good to think about?

12. Has anything ever surprised you in a really good way?

13. Is there an experience you’d recommend everyone try at least once?

14. Which trip, event, or hangout do you still bring up sometimes?

15. When was the last time you felt proud of yourself?

16. Do you have something from your past that always makes you smile?

17. Have you ever done something spontaneous that worked out better than planned?

18. Was there a phase of your life you low-key loved?

19. How did you find one of your comfort activities?

20. Can you think of a moment when you felt really present and happy?

2. Ideas or opinions

If experiences tell you where someone’s been, ideas and opinions tell you how they think.

This is where knowing the right questions to ask your crush can get interesting.

You’re not asking for facts. You’re asking for perspective. And perspective is attractive.

It shows how someone processes the world; whether they’re reflective, playful, skeptical, optimistic, or unexpectedly nuanced.

When you start asking questions to your crush about their opinions, you move beyond their biography and into worldview.

DEEP QUESTIONS TO ASK YOUR CRUSH

22. Do you think people change a lot over time, or mostly stay the same?

23. What’s an opinion you have that you’ve changed your mind about?

24. Is there something most people love that you just don’t get?

25. Do you think luck matters more than effort, or the other way around?

26. What’s a small thing people underestimate way too much?

27. Do you believe timing is everything, or do people use that as an excuse?

28. What’s something you think everyone should experience at least once?

29. Is it better to be really good at one thing or decent at lots of things?

30. Do you think people are more driven by fear or curiosity?

31. What’s a trend you secretly hope never comes back?

32. Do you think comfort zones are overrated or necessary?

33. What’s a belief you hold that’s shaped how you live your life?

34. Do you think overthinking is more of a flaw or a sign of depth?

35. What’s something people take too seriously that doesn’t need to be?

36. Do you think success is more about talent or consistency?

37. What’s an idea you find fascinating even if you’re not sure it’s true?

38. Do you think people need routine to thrive, or freedom?

39. What’s something society praises that you’re skeptical about?

40. Do you think it’s better to plan things out or figure them out as you go?

41. What’s a question you wish people asked more often?

3. What you’re building or excited about

If you really want to level up your questions to ask your crush, start asking about what they’re building.

Not in a résumé way. Not in a “so what do you do?” way.

You’re asking about what they are most passionate about?

Everyone is building something even if it’s small. A habit. A routine. A creative project. A healthier mindset. A new phase of life.

When you start asking questions to your crush about what they’re excited about right now, you become their favourite person to talk to.

Also fyi, when people talk about what they are most interested, they look 10x hotter!

TEXTS TO SEND YOUR CRUSH

42. Where is most of your energy going right now?

43. How are you trying to improve yourself these days?

44. Lately, what’s been motivating you to get out of bed?

45. Which part of your life feels under construction?

46. Are you committing more seriously to anything right now?

47. Has a project started showing real progress yet?

48. Looking a few months ahead, what are you excited to see the results of?

49. Do you feel yourself moving in a clear direction lately?

50. Is there something you’re choosing to prioritize right now?

51. Are you building something that future-you will appreciate?

52. Has your focus shifted away from anything recently?

53. Does anything feel especially worth the effort lately?

54. Are you saying “yes” to anything more often these days?

55. Do you feel a sense of momentum anywhere in your life?

56. Where are you investing most of your time right now?

57. What’s something that’s starting to click for you?

58. Do you feel curious to explore something next?

59. Is anything taking shape slowly but meaningfully?

60. Has anything been fueling your optimism lately?

61. Is there something you’re proud of working towards?

4. Culture

Culture is bigger than music, art, or fashion but it includes all of that too. It’s how someone moves through the world. What they notice. Things they value. What feels like “home” to them.

When you’re thinking about questions to ask your crush, culture is an underrated goldmine.

That is because asking your crush the questions reveal their taste, environment, rituals, humor, and style.

These can become surprisingly end up being deep questions to ask your crush, even when they start casually.

Talking about aesthetics often leads to identity. Speaking about traditions leads to values. Sharing their favourite music or film leads to deeper emotions.

Culture sits at the intersection of experience and opinion.

WHAT TO ASK YOUR CRUSH

62. Is there something you love that most people around you don’t really care about?

63. Are you more of a minimalist or a maximalist?

64. Do you think where you live has changed your style or taste?

65. What’s a small cultural thing that weirdly matters to you?

66. What do you tend to notice first when you walk into a place?

67. What’s something popular that just doesn’t click for you?

68. Where do you feel most in your element?

69. Do you think taste is something you’re born with or something you pick up?

70. What kind of places make you want to hang out longer than planned?

71. What’s something you love that you’d never call a “favorite”?

72. Do you dress more for comfort or expression?

73. What feels “home” to you that isn’t a person?

74. How do people signal taste without talking about it?

75. What kind of stories feel most familiar to you in films or books?

76. When you think about “good design,” where do you notice it most in everyday life?

77. What role does music play in your life?

78. What’s a norm you didn’t realize was specific until you met people from elsewhere?

79. How do people around you usually unwind?

80. What does success look like in your environment?

81. How early or late is “late” where you’re from?

82. What’s something you’d miss immediately if you left your city or community?

83. How do people typically show respect where you’re from?

84. What role does money play in everyday conversations around you?

85. What’s a shared experience that instantly bonds people in your culture?

86. How much do people value privacy versus openness where you are?

5. Thoughtful questions

These can easily become some of the most powerful deep questions to ask your crush, because most people don’t get asked them.

It means you’re curious about who they’re becoming, not just who they’ve been. You’re paying attention to how they think, how they evolve, how they experience the present.

That kind of curiosity feels rare. And rare feels special.

Because at the end of the day, asking good questions isn’t about being impressive.

It’s about being genuinely interested.

QUESTIONS TO ASK YOUR CRUSH

87. How have you changed in small ways over the years?

88. How do you usually spend a day when no one needs anything from you?

89. What kind of people bring out your best side?

90. What’s something simple that consistently makes your day better?

91. How did your personality shift as you got older?

92. What feels easier in your life now?

93. How do you usually recharge after a long week?

94. What kind of environments bring out your best side?

95. How do you know when you’re genuinely happy?

96. What’s something you didn’t expect to enjoy as much as you do now?

97. How has your idea of “fun” changed over the years?

98. What habits have stuck with you over time?

99. How do you usually handle uncertainty?

100. What makes a day feel well spent to you?

101. How has your relationship with friendships evolved?

102. What kind of conversations energize you?

103. How do you decide who gets your time and attention?

104. What’s something you’ve grown more comfortable with?

105. How do you usually celebrate small wins?

106. What helps you feel grounded?

107. How do you know when you’re in a good phase of life?

108. How do you like to spend slow days?

109. What feels different about you compared to five years ago?

110. How do you usually handle days that feel off?

111. What kind of memories do you find yourself replaying?

112. What parts of yourself feel the most consistent?

113. How do you know when something is right for you?

114. What kind of experiences make you feel most alive?

115. How do you reset when life feels overwhelming?