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Awkward. The Questions That Lead To Love

With every true friendship, we build more firmly the foundations of which the peace of the whole world rests. Mahatma Gandhi


Graduation. Parties. Family. Friends. Strangers. AWKWARD. It doesn't happen just in middle school (photo from book I just ordered for younger grandchildren).




AND opportunities for connection.


My two granddaughters and I, along with their parents, were glad to help celebrate the graduation of one family friend and three of his classmates. When we arrived at the gathering, the place was packed. We only knew the people who had invited us. As it turned out, it was the same situation for most everyone.


Intimidation was a bit of what I was feeling. These sorts of events can activate a stress response for many of us. Our internal system is telling us that we are being chased by a lion. Help! Where’s a corner to slink into? The food and drink table? Maybe we give ourselves a pep talk and remind ourselves that it’s not about us and it’s just a painful situation to power through somehow.


Although these situations can be stressful, I do have a sincere desire to connect with others. I sat down near a couple of others, smiled, nibbled on my food, and asked a few questions. Pretty soon, I was able to find some common areas of interest. And then a surprising thing happened.


Keep in mind the assemblage of characters… teens, college students, parents, and grandparents scattered around in various groups. A college student, Mia – a sister of one of the graduates, sat down next to me and her grandmother. Strangers, different generations. It felt fun and different. Inevitably the conversation came around to me and my interest.


I tried to evade telling them that I was trying to write a book on compassion. That usually is a conversation stopper. But I decided to be courageous and just spit it out.


Mia looked intrigued. “Do you know The New York Times 36 Questions that Lead to Love?” she asked.


“Yes!” I responded with gusto. “Tell me how you know about it.”


“A friend of mine was stuck in a situation in which she was going to drive a stranger from San Francisco to San Diego and she was desperate to figure out how to handle the awkwardness of that situation. She found out about the 36 questions. They used it on the trip. Loved it. Then a whole group of us started sharing the questions with each other. After a while we started making up our own questions. We really want to connect with each other. Not necessarily in a romantic way, but just truly get to know each other. We also keep our eyes out for all those cards where you ask each other deeper questions which call for more trust, authenticity, and vulnerability.”


The people who devised the 36 questions, particularly psychologist Dr. Arthur Aron, would be as happy as I was to hear Mia’s story. The idea behind the questions is to see if two strangers can develop an intimate connection just from asking each other a series of increasingly personal questions. And, of course, the 36 question experiment went nuts after the columnist of Modern Love for The New York Times wrote about trying the questions out with an acquaintance…and ended up marrying the guy with whom she chatted.


Dr. Arthur Aron and his wife Dr. Elaine Aron had spent years researching intimacy and closeness. They believed that increasing self-disclosure, finding perceived similarities, and being open to closeness is the magic underneath the questions. In fact, they can be any questions which aid that process.


After the graduation party, my granddaughters (teens) and I began talking about the awkwardness of various situations and just trying to connect in general. I told them about a time that I was asked to mentor some high school students in a sort of “touchy feely” program. I remember looking around at my little group and thinking it was a hopeless cause. But the first prompt was for us to take two minutes, each person, without interruption, was to finish this statement: “If you really knew me, you’d know that…”


Some instructions were given as to what sort of things to share (for example, going deeper than “I throw my covers off one leg at night”). Mentors were told to start the ball rolling.


By the time our little group finished that exercise, everyone was teared up. And, as I looked around, everyone seemed especially beautiful. I had learned more about myself AND had fallen in love with this little motley crew. Amazing! Plus, I thought I was moving into an altered state of consciousness. No joke. I was on a high.


After I told my story, one of my granddaughters said she had a very similar experience after using the same prompt in an Outward Bound program.


I still cannot fully account for what makes these sorts of deep encounters so very heartwarming, soulful, rewarding, and grippingly loving.


However, I do know that we are social creatures. Just standing beside a person when we have a tough situation energizes us, emboldens us, allows us to dip confidently into our resources. (More about this in a book called Awkward by Dr. Ty Tashiro. I have ordered the book, watched videos and interviews with him. He claims that people will forgive our inevitable awkwardness in situations around strangers if we clearly demonstrate the larger values of kindness and goodwill.)


So okay, a look at the questions, keeping in mind it’s not about the questions. (My granddaughters are also considering questions that might initiate comfortable “small talk” before getting right into “big talk.”)


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?


Set III

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 them 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 they might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.



And…asking questions without really listening to the response will sabotage the whole process. One little trick I use for myself is to check myself mentally every few minutes to see if I could paraphrase back what the person has said to me.


What encouraged me in this whole experience was that this college student was all stoked on this self-disclosure and intimacy relational process and that college students were using the questions to deepen their friendships. My granddaughters have also told me how disgusted they become with shallow, posing and posturing relationships. Maybe it's a bigger thing than I realized - this urge to deeply connect... ongoing in our younger set.


That gives me BIG hope today. Maybe authentic personal relationships will ultimately win the day rather than our smartphones. I’m going to keep contributing my little piece...working on boosting my courage - making connections even in those awkward situations where part of me feels like running away. (And I am keeping the faith with the upcoming generations).


How might we keep finding ways to connect and deepen our friendships?






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