Questions that Build Connection—and Maybe Lead to Love?

Don’t tell my wife, but I’ve been reading the “36 Questions That Lead to Love” in the New York Times. It’s not as bad as it sounds. Honestly, I was thinking about loneliness and the challenges of making friends, and I happened upon this article.

Let me explain: the U.S. Surgeon General recently released a report on loneliness. The report described loneliness as an epidemic that affects half of us. Even as our world becomes fuller and more interconnected, we are less together. And, importantly, being lonely is as bad for your health as smoking 15 cigarettes per day. 

The data on friendships also reflects these trends. Over the past twenty years, we are spending less time with friends, a drop from 30 hours a month to 10 hours a month. The number of people who say they have no friends has quadrupled from 3% to 12%. The numbers are particularly serious for young men.

It was this loneliness epidemic that led me to the “36 Questions That Lead to Love” or rather the underlying scientific article from 1997. I read this paper so you don’t have to. To summarize, the authors gave pairs of people 36 questions to discuss with each other over 45 minutes. The questions were grouped into three sets of increasingly personal questions. For example, the first set had the question, “For what in life do you feel most grateful.” A question from the third set was, “Tell your partner something you like about them already.” A comparison group of pairs received small talk questions that were not intended to build connection such as, “What was the best gift you ever received and why?” and “Describe your mother’s best friend.”

The results demonstrated the questions worked. Compared to the small talk group, the pairs that received the questions designed to build connection felt closer and more connected at the end of the 45 minutes. It didn’t matter whether the pairs were same-sex or opposite sex or if the individuals were women or men. It also didn’t matter if the pair disagreed on important issues like whether one should smoke.

Let’s admit that it’s a stretch to say feeling more connected after a 45-minute conversation leads to love (sorry, New York Times!). However, maybe it can lead to friendship. Perhaps part of our increasing loneliness and decreasing friendships is that we’re not as good at having meaningful conversation. Maybe this list of questions is a solution to this problem.

My gift to you is five of my favorites:

“If you could change anything about the way you were raised, what would it be?” (Set 1)

“If you could wake up tomorrow having gained any one quality or ability, what would it be?” (Set 1)

“Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?” (Set 2)

“What, if anything, is too serious to be joked about?” (Set 3)

“If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? What haven’t you told them yet?” (Set 3)

But I love most of the questions, and you can find the whole list at the end of the linked article. I plan to use them. Maybe they will help me get closer to people and feel a little less lonely.

Just don’t tell my wife.