13 Questions to Dive into Someone’s Soul and Kick a Conversation into High Gear
Forget small talk, do big talk instead.
Do you often find yourselves in conversations where you don’t know how to get past the small-talk stage?
Do your conversations often seem hollow?
Do you sometimes meet people that you would like to get to know more, but don’t know how to?
Do you sometimes feel awkward when you can’t think of something to say other than how nice the weather is today?
If you answered yes to at least one of these questions, this one is for you.
It was 11:30 am on a beautiful Sunday morning. The sun was shining through the window, showering the room with its warmth and light. I felt happy but exhausted. This was hardly surprising, given the fact that I hadn’t slept at all the previous night. Instead, I had been at a party until 6 am and then spent another five hours talking to a guy I just met. Five hours. Just he and I in his room, glasses of water in front of us and an ashtray between us.
How did this happen? How did I get so immersed in a conversation with a guy I just met a couple of hours ago? I’ll tell you: Conversation was flowing like the river Nile during the rainy season, mainly because we were asking each other the right questions.
I love to ask questions. I was a strenuous kid to have, with endless Why? chains and never-ending curiosity. Now that I am 27 years old, the curiosity hasn’t changed much, but the questions have.
I dislike small talk. Sure, it’s necessary when you first get to know someone, but after five minutes it just feels tedious. I don’t care about your university degree or your gym workout plan — I want to know who you are, as a person.
Don’t get me wrong. Light conversation can be fun. Hell, I wouldn’t want to deep dive with everyone I meet — it would be way too time-consuming and exhausting.
But every now and then, you meet someone that you want to take a conversation to the next level with. Every now and then, you want to go past the small talk and do the big talk. So here are a couple of questions that will help you to do so.
Drilling down into someone’s soul
Obviously, a good conversation consists of more than just asking the right questions. It’s asking the right questions, being a good listener when they are answered, and bringing a natural flow into your exchange. When you were just talking about your opinions on death and an afterlife, asking them if they’re a cat or dog person isn’t exactly the smoothest of transitions.
However, asking the right question can open up tons of new subjects and show you how the other person works — you’ll get to know about their fears, dreams, hopes, motivations, and ambitions. In other words, it lets you peek into their soul.
When asking these questions, keep in mind that some of them are lighter than others and match them with the flow of your conversation. Some of these touch upon topics that most people are only willing to talk about if they already know you to a certain degree and are comfortable with you. So jumping straight into What’s your biggest fear right after you introduced yourself might not be the smartest of ideas.
With that out of the way, let’s get started!
- Which three things do you think most about these days? Great place to start. It not only allows the other person to choose what they want to tell you, but you’re also likely to get a lot of information to bounce off from. If you want to know what someone is concerned about and what’s going on in their life right now, that’s the way to go.
- Is there something on your bucket list that you are afraid of but want to do nevertheless? Two things move people most: Their fears and their dreams. This one is a great way to find out about both of them in one go.
- Who are your best friends and why are you best friends with them? You can tell a lot about a person by what they are looking for in other people. We all have our friends for a certain reason. Some because they are good to talk to. Some because they are diehard optimists. Some because you can throw a mean party with them. We usually connect with people because they show certain character traits that we like — and often, these are the ones that we value and have ourselves as well. So when you ask a person what they like about their friends, there’s a good chance that these traits are some of their own as well. As the Japanese say: When the character of a man is not clear to you, look at his friends.
- What does your perfect weekend look like? This one is pretty light, but nevertheless, you can extract a lot of information from the answer. Is the person an early bird or a night owl? Does he prefer to be with himself or surrounded by lots of other people? What is important to them in their daily life? This one, too, will give you lots of topics to bounce off from.
- If you could put a sentence on a billboard for everyone to see: What would it be? Everyone has got a story, and everyone has got a message. This one will tell you about both. I once met a girl who told me that she would put up a warning sign that told people that birth control pills can cause thrombosis. When she was young, her doctor didn’t explain that to her, which not only sent her to hospital for quite a while but also took a severe toll on the lightheartedness of her teenage years. I definitely didn’t expect this, but that’s what you get for asking the right questions.
- What do people think about you that isn’t true at all? A great way to clean up false first impressions and avoid putting your foot into their mouth. Also, this will tell you a lot about the preconceptions the other person might be struggling with.
- Are you afraid of death? This one is a bit more philosophical but can go deep. You can learn a thing or two about what the other person’s take on life is and how they approach their limited time on earth.
- If you were to die in one hour, would you die happily? Similar to no. 1, this one is a great way to get to know more about how the other person’s life is going at the moment. In other words, are they living their dream right now?
- If you could change one thing about yourself (or your character), what would it be? We all have body parts or character traits we aren’t exactly proud of. Often, these are the reasons for many an insecurity or low self-esteem. Asking about these things gives you an insight into what someone is struggling with or how they view themselves. Plus, it’s a good way to gauge if they have an accurate self-image and good awareness.
- What was your latest insight or learning? I often ask this one purely out of curiosity. But besides the insights or learnings that the other person might tell you about, it tells you quite a bit about how much the other person thinks about themselves and the things that happen to them.
- If you were a fruit, which one would you be? This not only makes for a fun way to explore each other’s perk & quirks but also is a perfect opportunity to show you’re not taking yourself too seriously.
- What are you passionate about? I love this one for two reasons. First, it will get even the most close-lipped person to spill words like a stewardess coffee during turbulence. People love to talk about themselves and the things they’re crazy about. Second, people are usually very knowledgeable about their passions — they spend a lot of their time on them. If you always wanted to know more about painting and someone tells you they’re really into it — that’s a win-win.
- If you could go back in time ten years and tell your younger self something, what would it be? Our past experiences, failures, and mistakes shape us like nothing else. While not all of us have regrets, there is always something that we would do differently if we’d have the wisdom of our older selves — even if it just is investing in Bitcoin earlier.
- BONUS: If you could choose between a whale-sized hamster and a hamster-sized whale, which one would you pick? Think about the pros and cons carefully! Alright, this is purely for shits and giggles. Or is it? One thing that I have noticed when having deep conversations with someone is that you need to show that you aren’t taking yourself too serious. Deep talk is cool and important, but never forget to have fun and enjoy yourself. So go ahead and discuss the pros and cons of whale-sized hamsters and hamster-sized whales — you’re bound to have some interesting conversations.
The most powerful question of all
Out of all these questions (and the thousands more I have asked in my life), do you know which one is my favorite? It’s pretty much the simplest question there is. Are you ready? It is… drum roll…
Why?
Without this simple why, all of the above questions are inherently useless. Because if you want to drill down into someone’s soul, it isn’t enough to know what moves them, what they are afraid of or what they want the world to know. You also have to know why.
If you only take away one thing from this article, let it be this: Ask Why? more often.
Because everyone has a story, and everyone has a message. By asking Why?, you give them the opportunity to share theirs.
~ Moreno
If you’d like to improve your conversation skills, how about learning how to criticize someone properly? It’s a valuable skill to have and when the time comes, you wish you knew how to do it.
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