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36 Questions that Lead to Love

Hadley’s Intro:  How do you start or improve

a relationship? 

In Mandy Len Catron’s Modern Love essay, “To
Fall in Love With Anyone, Do This,” she refers
to a study by the psychologist Arthur Aron (and
others) that explores whether intimacy between two
strangers can be accelerated by having them ask
each other a specific series of personal
questions. The 36 questions in the study are
broken up into three sets, with each set intended
to be more probing than the previous one.


The idea is that mutual vulnerability fosters
closeness. To quote the study’s authors, “One
key pattern associated with the development of a
close relationship among peers is sustained,
escalating, reciprocal, personal
self-disclosure.” Allowing oneself to be
vulnerable with another person can be exceedingly
difficult, so this exercise forces the issue.

The final task Ms. Catron and her friend try —
staring into each other’s eyes for four minutes
— is less well documented, with the suggested
duration ranging from two minutes to four. But Ms.
Catron was unequivocal in her recommendation.
“Two minutes is just enough to be terrified,”
she told me. “Four really goes somewhere.”

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

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

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

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

9. For what in your life do you feel most

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

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

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

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

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

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.


Ask a thoughtful question and savor the response

to deepen intimacy in a relationship.

Hadley Finch

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