In our modern world of digital communication, there is an onslaught of surface-level chit-chat where we never truly get to know the other person. It can therefore be difficult at times to find people to engage in meaningful conversations with. The following questions will encourage a conversation that moves past small talk and builds a connection of authenticity and transparency. No matter if you’re at a social event, a date or a family gathering these questions are sure to reveal a lot about someone.
1. If you could travel anywhere in the world, where would it be and why?
There are countless fascinating places to discover in the world. By asking this question, you can get a feel for how big-world or small-town the other person’s imagination is. Maybe they’ve seen how beautiful the Eiffel Tower looks at night or how fascinating The Wall of China is IRL. Or perhaps they would love to discover the countryside of their own backyard. You might even get some ideas for future travel plans of your own.
2. If money didn’t matter, how would you spend your time?
By asking this question you gain insight into the person’s passions, interests, and priorities in life. Some people would prefer to continue pursuing their careers, others might devote their time to a passion project or traveling to every corner of the world while blogging about the journey.
3. Who is one famous person in history you would want to have lunch with?
With this question, you can get an understanding of what subjects the other person is interested in. Would they want to have lunch with a historical politician, musician, poet, or scientist? Perhaps they view this individual as a role model and want to absorb all the knowledge and advice they have to offer.
4. What is the first memory you have of your childhood?
Studies show that our earliest memories start as young as two-and-a-half years old. This question can make us feel nostalgic as it brings us back to a time when we were at our most innocent and playful stage. It could be the smell of their grandma’s freshly baked cookies or watching their first Disney movie. Whatever it may be, these early childhood memories tend to stay with us because they hold a special place in our hearts.
5. Do you still think about your first love?
They say we never forget our first love as the memories and lessons blend into our minds in a bitter-sweet way. No matter how long ago the relationship was or whether or not the person still thinks of their first love, the experience can leave a lasting impression. This question has the potential to cause the person to vulnerably reflect on the lessons learned and knowledge gained during that time.
6. If you could give your teenage self one piece of advice, what would it be?
With time comes knowledge and through this we earn the perspective of offering great advice. When asking someone this question you’re gaining an understanding of them and their past. Maybe as a teenager, they really wanted to pursue a degree in journalism but went to business school instead or always dreamt of living abroad for a year. We can learn a lot about someone by the advice they would give to their younger self as it shows what they have learned and experienced along the way.
7. What’s the most interesting book you’ve read recently and what did you learn from it?
This question offers a few clues about the other person. Firstly, what subjects or genres are they interested in such as fiction, fantasy, economics, or self-help? And second, what aspect about the subject resonated with them so much that they’re able to relay it back? And as a bonus—we all love good book recommendations.
8. What’s a hobby you’re interested in learning?
Depending on the answer maybe the two of you can do it together! That’s the great thing about hobbies, they can turn into something social like a book-club, going to a cooking class, or taking up surf lessons. Hobbies can also be solo such as drawing, reading, or writing songs. In this way, you’ll also find out if the other person leans more toward introversion or extroversion.
9. Describe your dream weekend getaway.
This is where our fantasies take flight. Do they prefer the excitement of the city or the tranquility of nature? Are they spending it alone or with their friends? Is the weekend jam-packed with activities or is the pace rather relaxed and spontaneous? This question reveals their lifestyle preferences and how they ideally like to spend their free time.
10. If you could only eat one type of food for the rest of your life, what would it be?
We all have more than one favorite cuisine. That’s what makes this question both fun and slightly challenging. Of course, this would never become a reality but playing around with the idea can make for an interesting conversation while activating your taste buds.
11. If you could only listen to one genre of music for the rest of your life, what would it be?
Similar to the last question, it can be difficult to name just one genre. After all, over the course of our lives, we spend a lot of time eating and listening to music. This question is interesting as it can reveal potential passions the person has. If they listen to electronic music then perhaps they also love to dance. If they prefer acoustic ballads then maybe they’re into singing or, in the case of rock music, it’s because they’re passionate about playing the bass guitar.
12. In your dream date scenario what would the two of you be doing and where?
This question can apply to anyone regardless of whether they’re single or dating. These types of dream-scenario questions are alluring as we can allow our imagination to run wild for a moment. It also shows how they like to connect on a romantic level with another person. Will it be something adventurous like sky-diving where the memories last a lifetime or would they rather do something purely romantic like a candle-light dinner on a beach?
13. What’s your favorite way to celebrate something?
We all love a celebration regardless of the occasion or level of achievement. It’s intriguing to find out how someone prefers to celebrate their wins. Maybe they like to throw lavish parties and pop bottles of bubbly or would prefer the intimacy of hosting a small dinner with friends and family. This insight also reveals what successes or milestones the person has achieved in life or is set to achieve. Life is filled with many blessings and successes, big and small. By asking this question we might come to discover just how much more we should be celebrating these wins.
14. If you could have a superpower, what would it be and why?
This is a classic fantasy question that is sure to bring about a light-hearted conversation. Perhaps their love of travel has them wanting to teleport or the idea of reading minds gives them a sense of being able to connect deeper with others. Whatever the case may be, get ready for some very interesting and unique answers.
15. Do you believe in fate, or do you believe we create our own path in life?
This question taps into deeper topics of life such as religion and spirituality. There isn’t one right answer as it’s based on what the person solely believes in, making it that much more interesting to talk about. This is also a great inquiry as it encourages people to become open-minded and even get inspired by one another. Fate is a topic that will interest anyone as it’s so fascinating.
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