74 + 17 questions to keep a conversation going and get to know the other person better

Has it ever happened to you that you’re with a person and you’re both quiet because

you can’t think of any questions to ask to maintain a conversation?

It’s happened to me a few times.

Of course it depends on whether the person in front of you is very talkative or not, but it could also be that if you see a person every day, in the end, “you run out of subjects” to talk about.

Therefore, with this post I’ll try to gather a few questions that I’ve been collecting and which can help you begin and maintain a conversation.

1. What did you do today at work/school/whichever place you were at?
2. What’s the best thing that happened to you today? Why?
3. What is the worst or most difficult or hardest thing that happened to you today? Why?
4. What did you eat today and with whom?
5. What is the weirdest thing you’ve ever eaten?
6. Have you worked on or studied something new today? What?
7. Who’s your best friend?
8. Do you have any idol? Why is that person your idol?
9. What is the most embarrassing thing you know?
10. Tell me something you admire and why you admire it.
11. What’s your favorite music/song?
12. What subject do you like the most/least at school or work? Why?
13. Are you proud of something you’ve done? What?
14. If you could buy anything from anywhere in the world, what would it be?
15. Have you ever been really angry?
16. If you could change the profession, what would you choose?
17. Is there something you’d like to be doing a few years from now?
18. What’s the best thing that has happened to you?
19. What’s your favorite place? Why?
20. What’s your favorite book?
21. What’s your favorite food?
22. What’s your best memory?
23. What’s your worst memory?
24. Do you think it’s okay to lie sometimes or under certain circumstances?
25. What do you most want the most?
26. Is appearance important to you?
27. How would you define a good friend?
28. How would your friends/co-workers/family members describe you?
29. How do you know someone is lying?
30. What’s the best thing about you?
31. What’s the worst thing about you?
32. Have you ever done anything brave?
33. Would you like to be rich and famous? why?
34. What’s the worst thing someone has said to you?
35. What’s your favorite movie?
36. What’s your favorite actor/actress?
37. Explain a time when you were sad.
38. What famous person/character would you like to be?
39. Have you ever been jealous of something?
40. What scares you the most?
41. What makes you happiest?
42. How are we alike?
43. How are we different?
44. Who’s been the best teacher/boss you’ve ever had?
45. If you could change something in the world, what would it be?
46. What’s the best dream you’ve ever had?
47. What’s the worst dream you’ve ever had?
48. What’s your favorite number? Why?
49. What’s your favorite color?
50. What color would you never put on a wall in your home/room?
51. What actor or actress would you like in the movie of your life?
52. Who would be your beloved in the movie?
53. If you had to spend a week without a cell phone, what would you miss the most?
54. Have you ever laughed so much that you peed your pants?
55. If you woke up tomorrow being from the opposite sex, what would be the
56. 3 most important things you’d like to do?
57. What was your first impression of me?
58. What’s your best physical characteristic?
59. In your opinion, what do you think is my best physical characteristic?
60. Have you ever collected anything? (stamps, movies, dolls…)
61. If you suddenly won 5000.- €, what would you do with it?
62. Do you have or have had a nickname?
63. What’s the most important thing to have in your fridge?
64. Where in the world would you like to live/be right now?
65. What would you like to do when you retire?
66. Are you a superstitious person? About what?
67. How old do you “feel”?
68. Have you ever wanted something you couldn’t have or buy?
69. If you had to choose the clothes that I’ll wear next time I go out with you,
70. what would it be?
71. Have you ever role played in bed?
72. What’s the most sensitive part of your body?
73. Do you have a memory that always makes you laugh?
74. Do you think you’re a good kisser?

Readers’ Bonus

1. If you had a superpower, what would it be and why?
2. If you could choose between being handsome and poor or rich and ugly
3. what would you choose? Why?
4. How would you define yourself in 3 words
5. Which weather do you like the most?
6. Do you like to go shopping? Why?
7. Do you like sushi? What’s your favorite flavor?
8. What would you do if you saw a tiger (or wild animal) on the loose?
9. Do you like going to the beach? Why?
10. Do you like going to the movies? Why?
11. Do you like going to the gym? Why?
12. What would you prefer, meeting the love of your life or being a millionaire?
13. What are your favorite combinations (clothes, colors, flavors…)?
14. If you could dine with a historical character, who would it be? why?
15. If you had to choose between your family and your partner, who would you choose? Why?
16. What sport do you like to do?
17. Would you like to travel and visit the world? Who would you go with?

Clearly, these questions can lead to long conversations.

You don’t need to ask them all at once.

Sometimes, I ask the questions game.

The game consists of asking the other a question and they have to ask me a question.

That’s also a good way to ask questions to keep a conversation going.

I’m sure that after this post you won’t have the excuse of “not knowing what to ask” because you now have plenty of ideas.

We could surely keep adding questions to the list. What other questions would you add?

You can leave them in the comments section.