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140 Engaging Questions To Ask Your Crush: Start Something Special
- Yaw Amoateng
- Apr 11
- 6 min read
What is in this article?
So, you’ve got a crush. Your heart skips a beat when their name pops up on your screen, and suddenly, even “hey” feels like a big deal. You want to say something interesting, something that gets them talking but not in a weird or try-hard kind of way. Just something that sparks a vibe.
We’ve all been there, overthinking that next message, trying to find the perfect opener or wondering how to move the convo past dry small talk. The truth? It doesn’t have to be that deep. Sometimes all it takes is the right question, a little curiosity, a little playfulness, and boom... connection.
This isn’t about impressing them with some genius line. It’s about being real, having fun, and seeing where the conversation takes you. If you're looking for smooth, engaging ways to talk to your crush without sounding like you're reading from a script, you’re in the right place.
Let’s get into it.
140 Questions To Ask Your Crush
Here’s a curated list of 200 questions to ask your crush. These questions are designed to spark curiosity, deepen connection, and reveal shared interests or values.
Getting to Know Your Crush
1. If you could get a tattoo in a prominent place, what would it look like?
2. What’s one wish you’d want granted right now?
3. How would you describe your relationship with your parents?
4. Who’s your best friend, and what do you love about them?
5. What’s your favourite childhood memory?
6. If you could invite any living person to spend a weekend with you, who would it be?
7. Do you believe in soulmates? Why or why not?
8. What’s the most embarrassing text you’ve ever sent?
9. What’s your idea of a perfect night?
10. Are you more of an introvert or extrovert?
Fun and Playful Questions To Ask Your Crush
11. If you could travel anywhere in the world tomorrow, where would you go?
12. What’s the weirdest photo on your phone?
13. Would you rather live in a messy, relaxed house or a perfectly tidy one?
14. What’s your guilty pleasure when no one’s around?
15. What’s the dumbest thing you’ve ever bought?
16. If you could be a superhero, what power would you choose?
17. What’s your go-to karaoke song?
18. Have you ever had a paranormal experience?
19. What’s your favourite joke?
20. Would you rather never binge-watch TV again or never go to a movie theater?
Deep and Thought-Provoking
21. When people think of you someday, what do you hope they remember most?
22. What’s your biggest regret in life?
23. What’s a lesson you learned the hard way?
24. Do you believe in fate, or do we create our own future?
25. What’s something you’re certain about in life?
26. What’s your definition of unconditional love?
27. Have you ever lost something valuable? How did you cope?
28. What’s your biggest fear?
29. What’s a cause you’d protest for?
30. Do you think happiness can be bought?
Relationships and Romance Questions To Ask Your Crush
31. Do you believe in love at first sight?
32. What’s your love language (words, touch, gifts, etc.)?
33. What’s your idea of a perfect date?
34. What’s the most romantic thing someone’s ever done for you?
35. How do you feel about public displays of affection?
36. What’s a deal-breaker in a relationship for you?
37. Have you ever had a long-distance relationship? What worked or didn’t?
38. What’s your favourite physical feature about yourself?
39. What do you find most attractive in a person?
40. Do you think opposites attract?
Hypotheticals and Quirky Questions
41. If you won $500,000, what’s the first thing you’d do?
42. Would you rather have unlimited money or unlimited love?
43. If you could time-travel to any era, where would you go?
44. What would you do if you found a wallet full of cash?
45. If you could erase one invention from existence, what would it be?
46. Would you rather be famous or anonymous but impactful?
47. If you could live in any fictional universe, which would you choose?
48. What animal do you think you resemble most?
49. If you could have dinner with any historical figure, who would it be?
50. Would you rather be able to fly or read minds?
Personal Growth and Values
51. What’s the best advice you’ve ever received?
52. What’s a habit you’re trying to break?
53. How do you handle stress or anxiety?
54. What’s something you’re proud of but rarely talk about?
55. What’s a skill you’d love to learn?
56. Do you think people can truly change?
57. What’s your philosophy on forgiveness?
58. How do you define success?
59. What’s a book or movie that changed your perspective?
60. What’s something you’re secretly passionate about?
Light-hearted and Flirty
61. What’s your favourite way to be flirted with?
62. What’s the most attractive quality in a person?
63. Do you believe in “the one”?
64. What’s your favourite cheesy pickup line?
65. What’s your idea of foreplay?
66. What’s the sexiest dream you’ve ever had?
67. Do you prefer cuddling or kissing?
68. Is there a smell that just makes someone more irresistible to you?
69. What’s your favourite love song?
70. How do you feel about PDA?
Hobbies and Interests Questions To Ask
71. What’s a hobby you’ve always wanted to try?
72. What’s your favourite way to spend a lazy Sunday?
73. Are you a morning person or night owl?
74. What’s your favourite season and why?
75. Do you prefer the beach or the mountains?
76. What’s your favourite comfort food?
77. Coffee or tea? How do you take it?
78. What’s your favourite genre of music?
79. What’s the last concert you went to?
80. Do you collect anything?
Work and Ambitions Questions To Ask
81. What’s your dream job?
82. If money weren’t an issue, what would you do all day?
83. What’s the worst job you’ve ever had?
84. Do you prefer working alone or in a team?
85. What’s a career goal you’re working toward?
86. If you could start your own business, what would it be?
87. What’s your biggest professional fear?
88. How do you balance work and personal life?
89. What’s a skill you’re surprisingly good at?
90. Would you rather be a leader or a follower?
Childhood and Nostalgia Questions To Ask Your Crush
91. What’s a childhood game you loved?
92. What’s something you believed as a kid that sounds silly now?
93. What was your favourite toy growing up?
94. Did you have a childhood nickname?
95. What’s a family tradition you cherish?
96. What’s the worst trouble you got into as a kid?
97. What’s a food you hated as a child but love now?
98. What’s your earliest memory?
99. What’s a TV show from your childhood you’d love to revisit?
100. What’s a skill you wish you’d learned as a kid?
Random and Fun
101. If you could only eat one food for the rest of your life, what would it be?
102. What’s the weirdest thing you’ve ever eaten?
103. Do you believe in aliens?
104. What’s your favourite dad joke?
105. If you could be any fictional character, who would you be?
106. What’s your favourite board game?
107. Do you have any phobias?
108. What’s your zodiac sign, and do you believe in astrology?
109. What’s your favourite meme?
110. If you could have any animal as a pet, what would it be?
Future and Dreams
111. Where do you see yourself in 5 years?
112. What’s a bucket-list item you’re determined to check off?
113. If you could live anywhere in the world, where would it be?
114. What’s a skill you’d love to master?
115. Do you want kids someday?
116. What’s your idea of a perfect home?
117. What’s a trip you’ve been dreaming of?
118. What’s a life lesson you’d teach your younger self?
119. What’s a cause you’d dedicate your life to?
120. If you could write a book, what would it be about?
Personal Favourites
121. What’s your favourite movie of all time?
122. What’s your favourite book?
123. What’s your favourite holiday?
124. What’s your favourite way to relax?
125. What’s your favourite app on your phone?
126. What’s your favourite childhood cartoon?
127. What’s your favourite type of weather?
128. What’s your favourite dessert?
129. What’s your favourite smell?
130. What’s your favourite thing about yourself?
Final Fun Ones
131. What’s your favourite dad joke?
132. What’s the weirdest food combination you enjoy?
133. What’s your favourite way to procrastinate?
134. What’s your favourite emoji?
135. What’s your favourite way to spend a rainy day?
136. What’s your favourite childhood Halloween costume?
137. What’s your favourite pizza topping?
138. What’s your favourite way to cheer someone up?
139. What’s your favourite thing about our conversations?
140. What’s a question you’ve always wanted to ask me?
These questions range from light-hearted to deep, ensuring you’ll never run out of things to talk about with your crush! Use them to spark engaging conversations and build a stronger connection.
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