Getting to know someone over text can be both exciting and fun.
Whether you’re chatting with a crush, a new friend, or just someone you’re curious about, asking the right questions can help spark deeper conversations and keep things interesting.
To help you out, here’s a list of 101 questions to ask a guy over text that will give you insight into his personality, interests, and life.
Fun and Light-Hearted Questions
Start with easy, playful questions to break the ice:
- What’s your favorite way to spend a lazy weekend?
- What’s the most random fact you know?
- If you could have any superpower, what would it be?
- Do you believe in aliens or ghosts?
- What’s the weirdest food combination you’ve ever tried?
- If you could live in any time period, when would it be?
- What’s the most embarrassing thing that’s ever happened to you?
- What’s your go-to karaoke song?
- Do you prefer sweet or salty snacks?
- What’s your guilty pleasure movie or TV show?
Questions About His Interests
Find out what makes him tick:
11. What’s a hobby you could talk about for hours?
12. Are you more into sports, video games, or books?
13. What’s your favorite kind of music or band?
14. Do you like to cook? If so, what’s your specialty?
15. What’s the last TV show you binged and loved?
16. Who’s your favorite actor or actress?
17. If you could learn any skill instantly, what would it be?
18. Do you like traveling? What’s your dream destination?
19. What’s the best concert or event you’ve ever attended?
20. Do you have a favorite childhood toy or game?
Personal and Thought-Provoking Questions
Dig a little deeper with these meaningful questions:
21. What’s your happiest childhood memory?
22. If you won the lottery tomorrow, what’s the first thing you’d do?
23. What motivates you to get out of bed every day?
24. Do you have a life motto or favorite quote?
25. What’s something you’re really proud of?
26. Who has influenced your life the most?
27. If you could change one thing about the world, what would it be?
28. What’s the most important lesson you’ve learned so far?
29. How do you handle stress or tough situations?
30. What’s a dream or goal you’re working toward?
Questions About Relationships
See how he feels about love, friendship, and connections:
31. What’s the best date you’ve ever been on?
32. What qualities do you value most in a friend?
33. How do you usually show affection or care?
34. What’s your love language?
35. Do you believe in soulmates?
36. What’s something a partner has done for you that you’ll never forget?
37. Do you prefer big gestures or small, thoughtful acts?
38. Have you ever had a childhood crush?
39. What’s your idea of a perfect date?
40. How do you like to spend time with someone you care about?
Career and Ambition Questions
Learn about his goals and passions:
41. What’s your dream job?
42. Did you always want to do what you’re doing now?
43. Who inspires you in your field of work or study?
44. What’s the best advice you’ve ever received about life or work?
45. Are you more of a leader or a team player?
46. What’s one thing you’d like to achieve in the next five years?
47. Do you believe in work-life balance, or are you all about the grind?
48. What’s the most challenging project or task you’ve ever worked on?
49. How do you celebrate career milestones or successes?
50. If money wasn’t an issue, what would you do for a living?
Random and Quirky Questions
Keep the conversation spontaneous and fun:
51. What’s your go-to comfort food?
52. Have you ever had a funny or strange dream?
53. If you were an animal, what would you be?
54. What’s the most random thing in your pocket or bag right now?
55. Do you have any secret talents?
56. What’s your favorite holiday or season?
57. Are you more of a morning person or a night owl?
58. If you could only eat one meal for the rest of your life, what would it be?
59. Have you ever had a nickname that stuck?
60. What’s the weirdest text you’ve ever sent or received?
Pop Culture and Entertainment Questions
Find common ground with movies, books, and more:
61. What’s your all-time favorite movie?
62. If you could live in a fictional universe, which one would it be?
63. Are you into Marvel or DC?
64. What’s a book that changed your perspective on something?
65. Who’s your favorite fictional character?
66. Do you like watching documentaries or thrillers more?
67. Have you ever been obsessed with a celebrity or influencer?
68. What’s the first movie you remember watching as a kid?
69. Do you prefer streaming or going to the theater?
70. What’s your favorite video game of all time?
Hypothetical and “What If” Questions
Let your imaginations run wild:
71. If you had to be stranded on an island with one thing, what would it be?
72. What would you do if you could be invisible for a day?
73. If you could relive any day, what would it be?
74. Would you rather fly or breathe underwater?
75. If you could meet any historical figure, who would it be?
76. Would you choose fame or fortune?
77. What’s one thing you’d do if you weren’t afraid of failing?
78. If you could live anywhere in the world, where would it be?
79. Would you rather time travel to the past or the future?
80. What’s something you’d do if you were President for a day?
Deep and Reflective Questions
End on a thoughtful note:
81. What’s a belief or value you hold strongly?
82. How do you define success?
83. What’s your biggest fear, and why?
84. If you could change one thing about yourself, what would it be?
85. What’s a lesson you wish you’d learned earlier in life?
86. Do you believe in fate or free will?
87. How do you handle criticism or failure?
88. What’s the most meaningful compliment you’ve ever received?
89. What’s one thing you’d like to be remembered for?
90. How do you define happiness?
Just for Fun: Rapid-Fire Questions
Quick questions to keep things interesting:
91. Pizza or burgers?
92. Dogs or cats?
93. Beach or mountains?
94. Coffee or tea?
95. Summer or winter?
96. Books or movies?
97. Early bird or night owl?
98. Comedy or action movies?
99. Sneakers or dress shoes?
100. City life or countryside?
101. Texting or calling?
Conclusion
These 101 questions are perfect for striking up meaningful and fun conversations with a guy over text.
Feel free to pick the ones that resonate with you the most or mix and match them to keep the chat lively.
Remember, the goal isn’t just to ask questions but also to actively listen and engage in the conversation.
Who knows? You might discover something truly special about him!
Which question will you ask first? Let us know in the comments!