91 This or That Questions to Ask a Guy to Know Him Better

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Most kids seem to naturally be able to connect with others and start friendships. They also seem to be excellent at asking questions! As we become adults, it becomes much harder to make the human connections that are so essential for our well-being.

It is no surprise that as we get older, we also seem more reluctant to ask questions. This is why games such as Would You Rather are so popular. They allow us to connect with others in a fun way. Another name for this type of question is the This or That question.

Why are This or That Questions an Effective Way to Get to Know Someone Better? 

This or that questions are a great way to get to know people. They can be asked at times when a long conversation isn't possible, or they can be interjected in the midst of a longer conversation. These seemingly innocent questions can tell you a lot about someone.

In fact, they are a great way to get to know some basics about a potential partner at the start of a relationship. Many of the questions are non-threatening, yet can still shed some light on what the other person finds important and what matters to them.

These questions are often easier to answer than open-ended questions. They require little thought, specify the exact thing you want to know, and seem less threatening than opening up your mind and heart fully.

The start of a new relationship is often a stressful time and these conversations make for great, low-key conversation starters. The answers can be filed away for future discussion, or they can be opened up for elaboration immediately.

91 This or That Questions to Ask a Guy

1. Shooting with a rifle or with a camera?

2. Ocean or mountains?

3. Roller coasters or bumper cars?

4. Text or phone calls?

5. Foresee the future or change the past?

6. Sporting event or Philharmonic concert?

7. Collect sea shells or collect trading cards?

8. Misunderstood after death or forgotten after death?

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This or that questions are a great way to get to know people.

9. Underestimated or overestimated?

10. Logic or emotion?

11. Yoga or Karate?

12. Hear a painful truth or hear a comforting lie?

13. Get a requested item as a gift or be surprised by a gift?

14. Massage or acupuncture?

15. Yelled at or given the silent treatment by a loved one?

16. Emergency fund or travel fund?

17. Noise or quiet when sleeping?

18. Sleep in snow or dance in rain?

19. Be powerful or be popular?

20. Organized religion or generally spiritual?

21. Fund an animal sanctuary or fund a children's art center?

22. Stuck in line or in a traffic jam?

23. Full phone battery or full gas tank?

24. Vegetable garden or aviary?

25. Blogging or journaling?

26. Loose guidelines or clear directions?

27. Physical work or mental work?

28. Animals or people?

29. Be embarrassed or be afraid?

30. Loud neighbors or nosy neighbors?

31. Stranded on a desert island or trapped in a room?

32. Physically disabled or terminally ill?

33. Never be rejected or never fail?

34. World with no crime or no privacy?

35. Live alone in the wilderness or in solitary confinement in prison?

36. Remember everything or forget everything?

37. Rich and bored or employed and tired?

38. Vacation abroad or travel throughout this country?

39. Bicycle or motorcycle?

40. Passenger or driver?

41. Multi-tasking or mindfulness?

42. Physical books or e-books?

43. In-store shopping or online?

44. Dress shoes or bare feet?

45. Art gallery or history museum?

46. Snowball fight or water balloon fight?

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A great way to get to know some basics about a potential partner at the start of a relationship.

47. Have lots of kids or adopt lots of dogs?

48. Starry night or thunderstorm?

49. Front porch or back porch?

50. Be better at writing or better at speaking?

51. Want people to think you are honest or think you are kind?

52. One great friend or ten okay friends?

53. Comedy or Horror?

54. Abstract paintings or landscapes?

55. Run a marathon or compete in a trivia contest?

56. Laser tag or escape room?

57. Holiday dinner with family or volunteer at soup kitchen?

58. Tell a white lie or a painful truth?

59. Forgive easily or hold a grudge?

60. Spontaneous trip or completely planned itinerary?

61. Be an artist or be an athlete?

62. Have more time or more money?

63. Be able to speak any language or be able to talk with animals?

64. Work 4 days with long hours or work 6 days with short hours?

65. Always summer or always winter?

66. Prefer talking or prefer listening?

67. Seafood or steak?

68. Hot dogs in the park or dinner at a fancy French restaurant?

69. Teamwork or solo project?

70. Get up early or stay up late?

71. Work at a large corporation or small garage start-up?

72. Work from home or work in an office?

73. Explore the deep ocean or explore deep space?

74. Travel through time or transport through space?

75. Own a yacht or own a private plane?

76. Dog or cat?

77. Be the teacher or be the student?

78. Fiction or non-fiction?

79. Lose all thought or lose all feeling?

80. Star of the show or backstage?

81. Always day or always night?

82. Get one amazing gift or ten okay gifts?

83. Halloween or Christmas?

84. An hour in a walk-in freezer or two hours in a sauna?

85. Read a book or watch a movie?

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The start of a new relationship is often a stressful time and these conversations make for great, low-key conversation starters.

86. Outdoor jazz festival or opera at the theater?

87. Never sleep again or never eat again?

88. Swim with sharks or enter a lion's den?

89. Be super strong or be super smart?

90. Travel by train or travel by ship?

91. Rock climbing or deep-sea diving?

How and When to Ask This or That Questions

The great thing about this or that questions is that they can be adapted to any social situation and any type of relationship. These questions will open up conversations with people you just met or help you get to know friends, coworkers and partners better.

They can be fun, non-threatening questions for newer relationships or they can become deeper and intense when you have reached the stage of getting to know a guy on a deeper level. You can initiate a This or That game or scatter the questions throughout a conversation.

Surprising someone with a question randomly can show them you are spontaneous. Honestly, the options are limited only by your own comfort zone.

[See Deep Questions to Ask for Interesting Conversation]

Final Thoughts on This or That Questions to Ask a Guy

Getting to know people can be less intimidating when you find common ground. Asking this or that questions is a great activity for a casual first date. Learning to start step out of your comfort zone and return to that inner child who loved asking questions will help you start to come out of your shell too.

It will relieve much of the stress that comes from getting to know someone and it will lead to an opening for deeper conversations. You don't have to look far for more fun this or that questions for adults. You just may find that a great round of this game becomes your favorite way to meet people.

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