100 Hilarious Questions to Spark a Fun Conversation on Online Dating

1. If you could be any fictional character for a day, who would you choose?
2. Do you prefer pizza or tacos? (This one could start a heated debate!)
3. If you could only listen to one song for the rest of your life, what would it be?
4. Would you rather fight one horse-sized duck or 100 duck-sized horses?
5. What’s the most embarrassing thing that’s ever happened to you?
6. If you could trade lives with any celebrity for a week, who would it be?
7. Would you rather have a pet dragon or be a mermaid?
8. Do you believe in ghosts or aliens?
9. What’s the weirdest dream you’ve ever had?
10. If you were stranded on a deserted island and could only bring three things, what would they be?
11. If you could have any superpower, but it had to be completely useless, what would it be?
12. Do you have any irrational fears, like a fear of clowns or cotton balls?
13. If you could switch lives with any fictional character, who would it be?
14. What’s your favorite dad joke?
15. If you could only eat one type of food for the rest of your life, what would it be?
16. Do you have any hidden talents that most people don’t know about?
17. If you could travel back in time and witness any historical event, which one would you choose?
18. What’s the most embarrassing thing in your Netflix watch history?
19. Would you rather have a rewind button or a pause button for your life?
20. If you could only use one social media platform for the rest of your life, which one would it be and why?
21. If you could only wear one color for the rest of your life, what would it be and why?
22. Do you have a signature dance move? If so, can you show me?
23. If you could be any animal for a day, what would you choose?
24. If you could have any job in the world, what would it be?
25. What’s your favorite meme or GIF?
26. Do you have any funny nicknames from your childhood?
27. If you could live in any era, which one would you choose and why?
28. If you were a superhero, what would your catchphrase be?
29. What’s the funniest prank you’ve ever pulled on someone?
30. Would you rather have to speak in rhyme all the time or only be able to communicate through interpretive dance?
31. If you could be a character in any TV show, which show would you choose?
32. Would you rather live without internet or without air conditioning?
33. If you could only watch one movie for the rest of your life, what would it be?
34. Do you believe in ghosts or supernatural beings? Have you ever had a paranormal experience?
35. Would you rather have a rewind button or a fast forward button in your life?
36. If you could switch lives with any person for a day, who would it be and why?
37. What’s the weirdest food combination you’ve ever tried and actually liked?
38. If you could only listen to one musician for the rest of your life, who would it be?
39. If you could have any exotic animal as a pet, which one would you choose?
40. Do you have any guilty pleasures when it comes to TV shows or movies?
41. Would you rather have to wear a clown wig every day for a year or a tutu every day for a year?
42. If you could have any fictional character as a best friend, who would it be?
43. What’s the most ridiculous thing you’ve ever done for love?
44. If you could travel anywhere in the world right now, where would you go and why?
45. What’s your favorite ice cream flavor and why?
46. If you could only have one hobby for the rest of your life, what would it be?
47. Would you rather have a personal chef or a personal assistant?
48. What’s the funniest joke you know by heart?
49. If you could have any celebrity as your imaginary friend, who would it be and why?
50. Would you rather be able to talk to animals or speak every language fluently?
51. If you could be any Disney character, who would you choose and why?
52. What’s the craziest thing you’ve ever eaten?
53. If you could have any superpower, but it only worked when you were asleep, what would it be?
54. What’s the most embarrassing thing that’s ever happened to you on a date?
55. If you could trade places with anyone in history for a day, who would it be and why?
56. What’s your go-to karaoke song?
57. If you had to eat one food for the rest of your life, but it had to be served on a stick, what would it be?
58. What’s the weirdest dream you’ve ever had?
59. If you could have any job for a day, what would it be and why?
60. If you could be any fictional character’s pet, who would it be and why?
61. If you could have any animal as a pet, but it had to be miniature-sized, what would you choose?
62. If you could only have one type of cuisine for the rest of your life, what would it be?
63. What’s the most ridiculous fashion trend you’ve ever tried?
64. If you could be any character from a book or movie, who would you choose and why?
65. What’s the funniest pick-up line someone has ever used on you?
66. Would you rather have a talking parrot or a miniature elephant as a pet?
67. If you could be any age for the rest of your life, what age would you choose and why?
68. What’s the weirdest talent you have?
69. If you could only have one type of dessert for the rest of your life, what would it be?
70. What’s the most embarrassing song on your playlist?
71. If you could have any fictional creature as a pet, what would it be and why?
72. If you could switch lives with any celebrity for a day, who would it be and why?
73. What’s the most embarrassing thing in your room right now?
74. If you had to eat one color of food for the rest of your life, what color would it be?
75. What’s the most unusual hobby you’ve ever tried?
76. If you could have any job in the world, but it had to involve wearing a ridiculous costume, what job would you choose?
77. What’s the most interesting fact you know?
78. If you could only eat one type of food for the rest of your life, what would it be?
79. What’s the weirdest thing you’ve ever eaten for breakfast?
80. If you could be any character from The Office, who would you be and why?
81. If you could only watch one TV show for the rest of your life, what would it be?
82. What’s the craziest thing you’ve ever done on a dare?
83. If you could only have one type of pizza topping for the rest of your life, what would it be?
84. What’s the most ridiculous thing you’ve ever purchased?
85. If you had to spend the rest of your life in a fictional world, which one would you choose?
86. What’s the worst haircut you’ve ever had?
87. If you could only listen to one music artist for the rest of your life, who would it be?
88. What’s the most interesting place you’ve ever traveled to?
89. If you had to pick one fictional character to be your roommate, who would it be and why?
90. What’s the weirdest thing you’ve ever seen in someone else’s house?
91. If you could only eat one type of cheese for the rest of your life, what would it be?
92. What’s the most ridiculous thing you’ve ever done in the name of love?
93. If you could have any superpower, but it had to be a completely useless one, what would it be?
94. What’s the most embarrassing thing you’ve ever done in public?
95. If you could live in any era, which one would you choose?
96. What’s the worst fashion trend you’ve ever followed?
97. If you could only wear one color for the rest of your life, what would it be?
98. What’s the most unusual thing you’ve ever eaten?
99. If you could have any celebrity be your personal assistant, who would it be and why?
100. What’s the weirdest dream you’ve ever had?

Remember, these questions are meant to be fun and light-hearted, so don’t take them too seriously. The goal is to have a good time getting to know each other and showing off your sense of humor.