36 Questions to Fall in Love and Perfect Days


This weekend, I drove to Houston with my roommate to spend one night with Bri, whom we used to share a Youtube channel with. I’ve never met her but have known her for five years. It felt natural and there was a lot of giggling and the three of us shared a giant bed. The next morning after a jaunt in a Houston park and lunch at my parents’, Ashley and I drove back up to Austin. On the way to Austin she asked, “Want to answer 36 questions and fall in love?”

I’ve heard and read a lot about these questions. They’re designed to make strangers fall in love and it’s backed by research. I only knew about one question. Question 18: “What is your most terrible memory?” I’ve heard about it because girlfriends have told me their boyfriends didn’t fully participate because of that one question. And yet these are meant to be answered by strangers!

Ashley and I are not strangers. We live together and we’ve been friends for five years. We met on Youtube. We’ve traveled together and ate a lot of brunches and consumed a lot of coffee even before living together. I had an idea about what her terrible memory is but never wanted to pry and ask for details. I wrongly assumed I already told her my most terrible memory because it’s such a defining moment in my life that I’ve taken two decades to process. As we listened to each other’s abbreviated life stories (Question 11: “Take four minutes to tell your partner your life story in as much detail as possible.”) and then sat through each other sharing our terrible memories, I felt my love for my friend and roommate deepen.

It’s such a treasure when someone shares with you their past pain or greatest pain. When you see someone’s light come through his or her personality and your interactions, it’s already such a gift. Then imagine being given insight to the darkness. The light and joy of the person can now be appreciated as a miracle. Here they are, laughing and smiling with you despite really ugly shit. And nobody is spared the ugly shit. It’s the price we pay for the privilege and adventure of being alive (see the last line of this beautiful essay by Oliver Sack). Question 18 is a hard question but it points to someone’s resilience and resilience is beautiful.

I think my favorite question though is Question 4. “What would constitute as a perfect day for you?”

Yesterday was a perfect day. I woke up in an king-sized bed with two beautiful girls and indulged in a high-calorie breakfast with them. I saw one of my best friends briefly at a pretty park and had lunch at my parents’ house with my roommate. We answered the 36 questions in the car and I spent the evening eating and cuddling with Sugarface and Bob the Dog, ignoring the Oscars and mostly just being quiet.

Questions: Have you gone through these questions with anyone? If so, did you fall in love? If not, tell me about one of your perfect days.