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36 Questions to Ask on Your Next Date

Aug 18, 2016

KWP-JessNealProposal-1030 (1)

Photo captured by Kina Wicks just seconds after Neal proposed

Have you heard of the “36 questions that lead to love?” 

I honestly don’t recall how I first stumbled upon them, but it was in the New York Times several months back. In this article, to be exact–“To Fall in Love With Anyone, Do This.”

Written in January of 2015, I was obviously very well in love with Neal at this point, but it still proved to be equal parts intriguing and inspiring. (Regardless of your relationship status, I definitely recommend giving it a read.)

Essentially, the article is a personal essay about love. To give you the lay of the land– author, Mandy Len Catron, had just read about an experiment where psychologists succeeded in making two people fall in love with one another.

In this experiment, the psychologists asked two heterosexual people–one male, one female, to answer a series of 36 questions designed to establish emotional intimacy in just 90 minutes–a level that would typically take months, even years, to reach under “standard dating” circumstances.


The result?

The science experiment was successful. The two were engaged months later–they invited the entire lab to the wedding!

Fast forward to the author’s personal experience–when the topic of “falling in love” came up on a date, the night took an unexpected turn–the experiment was googled, and soon after, she found herself passing an iPhone back and forth, answering this series of 36 intimate questions with a man she barely knew.

The questions are broken into three sets–personally, I would rate them a low, medium, and high level of awkwardness and intensity.

For example, the first set of questions being similar to, “Given the choice of anyone in the world, whom would you want as a dinner guest?” and the questions of the last set being more along the lines of, “If  you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?

After these questions are answered, the final step is to stare into one another’s eyes for four minutes straight. Which she did–with success.

Now I’m sure you’re wondering–after implementing this little experiment, did she too, end up falling in love?

She did. 


My personal experience

This experiment, of course, was designed to foster closeness with someone you don’t know very well–maybe you’re on a third Tinder date, or re-connecting with a guy you had a crush on in high school.

But, despite being in a 3 year relationship, I loved the idea, and was inspired to try it anyway.

One late night on our trip to Paris, having [very late night] drinks at a sidewalk cafe, Neal and I pulled out my phone and started to go through a few of the questions. Despite not even getting through the first set, it was one of my favorite conversations we’ve ever had on a date.

So often, it’s easy to fall into that “standard chit chat” after you’ve been dating for several years–you know, “How was your work day, honey?” and “Oooohh we should really mop the floors this weekend!”

What’s funny, is that, while we know each other inside and out, I really had no idea what was going to come out of his mouth at the moment he answered some of these questions.

(This is coming from a couple guilty of not just finishing each other’s sentences, but literally having the same thoughts at the same time–where I open my mouth to say something but he beats me to the punch seconds before. Yet, here were several conversation topics we had never approached.)

To be honest, I don’t even remember which questions we answered, or how we answered most of them (there was a lot of wine involved) but I’ll never forget the feeling–it was so romantic an unexpected to have a discussion that felt new, unknown, and like we were getting to know one another for the first time all over again.

Curious as to what the rest of the questions are?


The questions

Set I

1. Given the choice of anyone in the world, whom would you want as a dinner guest?

2. Would you like to be famous? In what way?

3. Before making a telephone call, do you ever rehearse what you are going to say? Why?

4. What would constitute a “perfect” day for you?

5. When did you last sing to yourself? To someone else?

6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?

7. Do you have a secret hunch about how you will die?

8. Name three things you and your partner appear to have in common.

9. For what in your life do you feel most grateful?

10. If you could change anything about the way you were raised, what would it be?

11. Take four minutes and tell your partner your life story in as much detail as possible.

12. If you could wake up tomorrow having gained any one quality or ability, what would it be?


Set II

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

14. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?

15. What is the greatest accomplishment of your life?

16. What do you value most in a friendship?

17. What is your most treasured memory?

18. What is your most terrible memory?

19. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?

20. What does friendship mean to you?

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

22. Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.

23. How close and warm is your family? Do you feel your childhood was happier than most other people’s?

24. How do you feel about your relationship with your mother?


25. Make three true “we” statements each. For instance, “We are both in this room feeling … “

26. Complete this sentence: “I wish I had someone with whom I could share … “

27. If you were going to become a close friend with your partner, please share what would be important for him or her to know.

28. Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.

29. Share with your partner an embarrassing moment in your life.

30. When did you last cry in front of another person? By yourself?

31. Tell your partner something that you like about them already.

32. What, if anything, is too serious to be joked about?

33. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?

34. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?

35. Of all the people in your family, whose death would you find most disturbing? Why?

36. Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.


What do you think–will you try this experiment on your next date? 

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