36 Engaging Questions to Deepen Your Connection on a Date

May 31, 2024

In the past dating counseling, one of the most frequently encountered problems is: “I met a guy/gal who I like very much on XX. I want to communicate further, but I can’t seem to find any topics on our date?”

The underlying meaning of this sentence is also

“I don’t know what topics on our date to talk about, so I can quickly become familiar with someone.”

“What questions should I ask him/her as topics on our date?”

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Yes, when two people who have no intersection at all want to get to know each other in-depth, you can’t ask questions such as what you had for dinner.  You need to be able to explore each other’s inner thoughts. But if you directly ask “What is your dream?” to someone you have just met, it would be too abrupt.

When I was shopping in Tokyo one time, I suddenly found such an activity. The activity enumerated a lot of questions so that the people participating in the activity could communicate with each other. Everyone was watching happily and had a great conversation.

If you can predict a future event, what do you want to know?

What superpower do you most want to possess, and what are you going to do after possessing it?

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Say, if you are about to pass away tonight. It is too late to say goodbye to anyone. What is your biggest regret?

These questions make it easier for strangers to communicate with each other and allow both parties to get to know each other in an interesting way. Questions that would be interesting topics on our/your date.

The following paragraphs are reproduced from a classic sociological experiment

There was such a column in the “New York Times”: “To Fall in Love With Anyone, Do This” (To Fall in Love With Anyone, Do This).  It was ranked first in the number of hits on its website that week. The author of this article is a university professor in Vancouver. She tells that she and a strange man she just met, imitating an experiment done by American psychologist Arthur Aron in 1997, quickly cultivated a relationship to fall in love.

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This “topic on our date” article is not a rigorous academic paper, and the author’s experience is also half-joking.  But the experiment of “falling in love with strangers” mentioned in her article has aroused many people’s interest. The article is not only on social media that formed a tendency to occupy the screen; many media also reported it.

The strangers who participated in the experiment sat in groups in pairs. It took only 45 minutes to ask each other 36 magical questions and quickly developed a good feeling and intimacy with each other. The results of the experiment are fascinating. After discussing these questions, 30% of people immediately said that the relationship between themselves and the experimenters in the same group had become deeper than any other relationship in their lives.

After a while, 37% of people sat together during class, and 35% were already dating (this school is messy! By the way, it’s the State University of New York at Stony Brook, with Stony Brook’s classmate). Another couple got married six months later, and they invited everyone to their wedding.

These questions are divided into three groups, which are progressively advanced according to the depth of the questions. It takes 15 minutes to complete each set of questions. The question feels a bit similar to the Proust questionnaire.

The first set of questions

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1. If you can choose anyone in the world, who would you like to invite to dinner?

2. Do you want to be famous? In which way?

3. Before making a call, do you practice what you want to say? Why?

4. What is a “perfect” day for you?

5. When was the last time you sang to yourself? When is it to sing to others?

6. If you could live to be 90 years old and you could choose to keep your mind or body at 30 for the next 60 years, which one would you choose?

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7. Do you have a secret hunch about how you might die in the future?

8. List 3 traits that you and the other party have in common.

9. What is the most grateful thing in your life?

10. If anything in your growth process can be changed, what changes do you hope to make?

11. Use 4 minutes to tell the story of your life to the other person in as much detail as possible.

12. If you can acquire any ability or trait after getting up tomorrow morning, what do you hope it is?

The second set of questions

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13. If a crystal ball could tell you all the truth about yourself, your life, or your future, what would you like to know?

14. Have you wanted to do something for a long time? The reason for not doing it yet?

15. What is your most outstanding achievement in life?

16. Which part of the friendship do you value most?

17. What is your most precious memory?

18. What is your worst memory?

19. If you knew that you would die suddenly within a year, would you change your current lifestyle? Why?

20. What does friendship mean to you?

21. What role do love and affection play in your life?

22. Take turns sharing what you think the other person has better personality traits. Raise 5 points each.

23. Is your family relationship close and warm? Do you think your childhood is happier than most people’s?

24. What is your relationship with your mother?

The third group of questions

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25. Say 3 sentences that contain “we” and are in line with the actual situation, such as “we are all in this room now”.

26. Complete this sentence: “I hope I can share with someone—”.

27. If you want to be a close friend of the other person, what should he or she need to know?

28. Tell the other person what you like about him or her (you must be very honest in answering this question and say things you might not say to someone you just met).

29. Share awkward moments in your life with the other person.

30. When was the last time you cried in front of others? When did you cry alone last time?

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31. Tell the other person what you like about him or her now.

32. Is there anything that you can never joke about?

33. If you will die tonight and cannot contact anyone, what do you regret the most for not telling others? Why haven’t you said it yet?

34. Your house is on fire, and all your things are inside. After rescuing your loved ones and pets, you still have time to rescue the last thing safely. What will you take? Why?

35. Among all your family members, whose death will hit you the most? Why?

36. Share a problem in your life and ask the other person what they would do if they encounter such a situation. At the same time, ask the other person to tell you how you feel about this issue from their point of view.

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This experiment shows a truth: the relationship between people from alienation to intimacy requires both parties to continuously analyze their hearts and constantly confess to each other.

Another interesting finding after the experiment is that the degree of intimacy between people is not directly related to whether their answers to the same question are similar. In other words, the same point of view is not a necessary condition for a close relationship between two people.

The final conclusion of this experiment is that if two strangers want to establish an intimate relationship quickly, they need to rely on both parties to dig and be honest about their true inner thoughts.

I hope this “topics on our date” article helped you in some way.

Articles you might like: Tips For A Successful First Date After Meeting Online10 Signs You’re Compatible With Your DateHow To Keep A First Date Light, Easy, And Flirty

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