Conversation starters that could change your life

In the summer of 2016, I found myself thumbing through a book in a small-town gift shop, simply titled “The Book of Questions”. I thought it would make a great icebreaker for my first year of university. Little did I know then that it would become my game-changer for good.

When a dear friend of mine asked me questions for the first time, we opened a floodgate and opened up to each other in a way we never had before. My first-year roommate and I giggled at its hypothetical scenarios for hours. When I posed the questions to a “Chad type” I was dating, he confessed that I’d gotten past his “alpha male persona” and gotten to know who he really was underneath it.

As a guest at a friend’s Thanksgiving dinner, I brought the questions along to pass the time on the drive. My book soon became the talk of the table. By the time I returned, I’d gained a second family and a lifelong best friend. A  few months later, I decided I would gift the book’s magic to a crush of mine, only to find its last copy at the same time as another customer. She’d been searching for a previous version released in the 1980s- the version that made its rounds through the conversations she was having in her twenties. Clearly, the questions have stood the test of time. From my experiences, they’ve stopped time entirely.

Case in point: A friend of mine once picked up the book right before our plans to go on a late-night adventure. Six hours of talking later, we never left my house- in the midst of asking questions, we realized we were more than friends, an adventure all its own. I’ve since taken questions along on every adventure I’ve been on, from the beaches of Maui to the jungles of Belize to the cobblestone alleys of Spain. I always keep questions tucked in my back pocket, ready to cut past small talk and get straight to connection. 

Why do I love to ask? Because deep down, I know that every person I cross paths with wants to feel seen. Our fast-paced world allows us the opportunity to get away with meaningless interaction all the time, displayed in our “I’m good” replies, our “hope you’re well” emails, and our “let’s catch up” texts. I believe people are too complex, too storied and too beautifully complicated not to have more interesting things to say. And if I get to find out even a sliver of those things, I consider my life all the better for it.

Perhaps this is an opportunity for you to start asking the people in your life questions too. Aside from physical touch, what better way is there to practice closeness than through conversation? I’ve hand-picked these ten just for you- but before you get going, I’ll let you in on one secret: the magic isn’t found in the questions themselves- it’s found in one’s openness to answering them.

THE QUESTIONS:

1. If a crystal ball could tell you the truth about one thing about yourself, the future, or anything else, what would you want to know and why?

2. Would you rather be very successful in a professional sense with a tolerable private life, or have a great private life and an uninspiring professional one? 

3. What is the most outrageous thing you’ve ever done? Do you feel more proud or embarrassed about said thing?

4. Would you like your partner to be smarter and more attractive than you? If so, what is it about you that would hold their interest?

5. How would you feel if you knew that within your lifetime, computers would become more self-aware, intelligent and creative than humans? Would it change the way you live your life now?

6. Has anyone been able to greatly influence your life within a short period of time? Do you think you’ve had that same effect on them, or had that effect on anyone else?

7. Would you rather have one true soulmate and no other good friends, or no soulmate and lots of good friends?

8. If you could return to a previous point in your existence, change a decision you’ve made, and pick up from there, would you?

9. If someone threw a party for you and invited everyone you’ve ever cared about, who would you be most excited to see? Who would you be most nervous about seeing?

10. If you died this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Do you think you’ll ever tell them?

Enjoy these questions - if any resonate and you’d like to send me your response, you can always reach me by email at tayalyjade@gmail.com.