72 Weird Questions to Ask for Awkward But Interesting Conversations

Asking questions is the best way to learn about someone. But, when your goal is to have some hilarious fun together, such weird questions to ask them can be the best idea. 

Whether you know someone from a long time or just recently met, such weird questions overall lead to unusual yet interesting conversations. 

In this list, you will find the best list of the weird questions that keep your conversation going like never before!

Weird Questions to Ask a Girl

When you don’t want to make someone bored in the initial conversation, these questions can be good ones to start the discussion. However, when asking such awkward questions to girls, you better be alert. Don’t worry; we provide the weird but good questions that are limited to ‘just for fun’ in this list. 

1. What will be your first reaction when you find that there are police on your door? 
2. What is something that you never wore but will try once to feel awkward? 
3. What do you prefer: being lost with a friend in the sea or with your partner in space? 
4. What if we slowly turned into monkeys again? 
5. Have you ever done something weird and your crush noticed that? 
6. Which animal makes more hilarious and awesome conversation than humans? 
7. Under which circumstances, will you punch yourself? 
8. What if you wake up and realize that you’re the only alive person in the world?
9. What is the weirdest reason someone ignores you? 
10. If you could replace your mind with one celebrity, who would be the one? 
11. What is the most awkward thing you ever bought from the general stores? 
12. What will you do first after landing on Mars? 
13. What girls too have a beard, how would you handle it?
14. Have you ever been frightened by your own shadow? 

Weird Questions to Ask a Guy

There are tons of weird things going on in the guys’ minds. But, if you’re running out of such crazy ideas and thoughts, this next list will hopefully help you. This list covers some weird and awkward questions you can ask a guy while chatting or in person. 

15. Anytime you forget your license at home, what excuse do you generally give? 
16. If you have a chance to decide your age and life era, which one would it be? 
17. Which superpower do you wish to have but later turn into a supervillain? 
18. What do you do if you get a giant elephant as your birthday present? 
19. If there was no vacation during the schooling what would be your first reaction? 
20. If you lose on any planet other than Earth, which one would it be? 
21. Which R-rated movies that you can’t watch but still prefer to see over again?
22. Which worst habit of your roommate do you wish you followed once to take revenge? 
23. What if you forget everything about your life and yourself? 
24. Are there any weird things you do around people when no one is watching? 
25. How many hours do you spend seeing yourself in the mirror? 
26. How long could you sit doing nothing or staring at the wall? 
27. Have you ever thought of stealing something from someone? 
28. What is something that you buy more often even though you don’t use it? 

Also read: Compliments for Boys [Ultimate Compilation]

Weird Questions to Ask Your Friend

Especially with your friends, such questions test their creative thinking and humor. So whether you want a list of questions for your best friend or group of friends, these are the perfect list of strange questions for having a perfect time together. 

29. What do you do if you get to meet all your look-a-likes at once? 
30. Have you ever got any hints from your past life? 
31. If you have the option to be in the dinosaur, which one do you choose to be? 
32. What is the most awkward dream that you never shared with anyone? 
33. How confident are you about your bathroom singing talent? 
34. No matter how much money someone gives, you never do what? 
35. What do you do if you get a chance to build the universe?
36. What is your first reaction when you listen to your recorded voice? 
37. Have you tried to win arguments even knowing you’re wrong?
38. How would you destroy all the planets in the galaxy? 
39. What is the worst punishment you have received from your parents? 
40. Your parents hate it when you do it, but you still do it. What is it? 

Weird Questions to Ask Your Girlfriend

It would help if you always had some unique topic and discussion to add a little surprise to your relationship. And when you don’t know the next funny questions to ask her, here are some funny and weird questions to have some awesome conversation with her. 

41. How do you torture turtles to leave their shells? 
42. What is something that you know better than your school teacher? 
43. Even being a pessimist, you still set the alarm for what? 
44. What is the weirdest lie you say to impress someone? 
45. How many sheep do you need to count to fall asleep? 
46. What is the first thing you do if you know that you’re losing the argument? 
47. What is your record of not taking a shower for how many days? 
48. Which is the funniest thing to do when you see a ghost in front of you? 
49. Which body part of yours do you want to change with plastic surgery? 
50. How do you communicate with others when you forget every word you know?
51. You go deep in the sea and cry for which reason? 
52. What is the weirdest job application you’ve ever seen or written?
53. If there’s one sport only for fat people in the Olympics, which one will it be? 
54. Which was the awkward thing you did during the office meetings?
55. How do you wipe the tears of fish that cry underwater?
56. What would you talk to wild animals that talk rather than roar at you?
57. What is the first thing you do when you wake up on mars?

Also read: Cute Nicknames (List) for Your Girlfriend

Weird Questions to Ask Your Boyfriend

When your boyfriend always got you with his jokes and pranks, you now have a good chance to pay him back. Here are some weird questions you can ask him to come up with a unique response and have a hilarious conversation. 

58. What is more trouble for you having an accent or not having one? 
59. Have you ever tried to prank someone but you got the even worst one? 
60. Which are those words you can’t successfully pronounce? 
61. Which animal family makes a better neighbor than your existing one? 
62. What is something normal to you but not to anyone else? 
63. Which last show did you binge-watch but regret after completing the series? 
64. How do you keep unwanted guests away from never visiting your place again? 
65. What is the worst way someone proposes and still gets accepted? 
66. Have you ever stolen something from your office then your boss found it? 
67. What you should not give to your partner on a first date? 
68. Have you ever done something at a family gathering that no one can forgive you for?
69. What are some best reasons that people will believe in ghosts and not in god? 
70. What do you do if your home is in the middle of the zoo?
71. Have you ever eaten anything from your pet’s plate?
72. Is there any craziest way you’ve injured yourself?

We hope you find some good topics to discuss with your friends and partner with this list of weird questions to ask. Indeed, these are awkward questions that look like they have no meaning to ask, but they may lead you to a shocking conversation with them when you ask.