What should I ask?

I know — finding the right question(s) to ask can be hard.

Don’t worry. I’ve got a few options for you, ranging from my own list, to other rad sets of questions I’ve explored over the years.

Or, take your chances with a random one of my favorites:

Once you’re ready, consider sharing back your story.

200+ Questions I’ve Collected

Over the last few years, I’ve kept a spreadsheet of questions that I’ve been asked, have heard in conversation, or just generally found interesting. If you don’t know where to start, I’d suggest picking / asking Siri or Google for a random number between 2 and 205.

Opia Cards

Opia was developed as an immersive experience, first realized during Sonder, where two strangers enter a space, sit directly across from one another, and ask a series of questions of their partner.

Using a deck of cards with 28 unique questions – ranging from "Are you sexually satisfied?" to "What is your greatest fear?" – these questions are meant to connect through a shared experience. 

36 Questions That Lead to Love

The New York Times lists 36 questions you can ask someone if you want to fall in love. (Or make your love even stronger.) This site linked above provides one way to explore these questions.

The { } And

An Emmy-award winning interactive project, The { } And, is an intimate look into real couples and explores the new frontier of relationships. They’ve created decks of cards for people to use in their own explorations, as well as a popular YouTube series documenting the conversations people have.

We’re Not Really Strangers

While I first came across their instagram account, WNRS is a purpose driven card game and movement all about empowering meaningful connections. Three carefully crafted levels of questions and wildcards allow you to deepen your existing relationships and create new ones. 

(another) Random Question Generator

Just one of many random question generators online, if the options above didn’t quite do it for you.