How to fall in love with anyone, the 36 questions redux

One of life's great pleasures for me is good conversation. To cut through the thick of inane small talk straight to the heart of what's real and important.

What makes you tick? Why are you here—in this bar, at this event, in this city, in this life? What last moved you? What do you wish you had said?

And what a blessing that I've surrounded myself with friends who have the curiosity, courage and depth to explore these soulful conversations with me. This has continued to nourish me during a pivotal growth period in my life.

I sincerely believe that a prescription for a happier, saner world lies in more true connection and less fluff. More heartfelt reaching out, and less of the passive or unuttered desire for bonding that traps us in loneliness.

Inspired by a New York Times phenom from last year, I've made a remix of 36 questions to ask to fall in love with someone. Slightly shorter (24 questions). For fun, for use, for the hell of it.

I've plucked the questions from my mental catalogue of some of the best real conversations I've had (I'm brazen like that); from questions I've always wished were appropriate to ask in lieu of "What do you do?"; and from the crowdsourced megabrain that is my group of Facebook friends.

The result is this mash-up of what I like to call deepeners. These questions let you skip the niceties and dive into the substance. Have they made me fall in love with a stranger yet? No. 

But they have made me fall in love with my friends.



Here's where you get to map out the contours of their life, their personality. It's discovery, with playfulness. The curation of their thought and how they present it to you will reveal plenty, and the exploration, if the chemistry is right, can be a fun romp into rapid mutual acquaintance.

  1. What do you wish you could help people with?
  2. What do people most often compliment you on?
  3. Describe your perfect Saturday.
  4. What would you do more of if you had more time?
  5. What do you never get tired of talking about?
  6. What’s one thing you have strong opinions about?
  7. What's something you've always wanted to try? Why?
  8. Why are you standing here right now? Start at age 10.

Hors d'oeuvres.

Now, substance. Depth. The beliefs and the feelings beneath the facts begin to emerge, slowly uncovering the unique shapes and colors of who they really are.

  1. Tell me about your greatest accomplishment.
  2. What’s your favorite quote and why?
  3. What’s one book you think everyone should read?
  4. Who most deserves a thank you letter from you? Why?
  5. Who do you most want to write a fan letter to? Why?
  6. What’s one quality you wish you had more of?
  7. Who or what inspires you lately?
  8. What three qualities do you most value in a person? (My personal favorite when meeting people I find interesting.)


Here, the truth. The stuff people won't share without a loving, present, explicit invitation. Here, you get to give someone the life-giving permission, finally, to put their truth, their uncensored stories into words. The privilege and intimacy of these journeys into someone's inner world can be enthralling, frightening, revelatory—and always humanizing.

  1. What experiences have been the key turning points in your life?
  2. Tell me about a time when your worldview really shifted.
  3. What would be too good to believe, if someone were to sit down and tell you what’s coming next in your life?
  4. What makes you come alive?
  5. What would be the highest compliment someone could pay you?
  6. What’s one thing most people don’t know about you?
  7. What do you still need to forgive yourself for?
  8. What do you most wish someone would have said to you in a time of struggle?

This is what it's all about. Because falling in love with someone by seeing who they are and giving them the truest version of you is among the most beautiful experiences we can have.

Allow this list to be your starting point to craft your own.