Most people are terrible at talking. We stick to the script. "What do you do for work?" "Where are you from?" It’s boring. Honestly, it’s a waste of breath because those answers don't tell you who a person actually is deep down. They just tell you what’s on their LinkedIn profile or their driver's license. If you want to actually connect, you need a better question to ask to get to know someone than just "How’s it going?"
Real connection is messy. It’s about finding the weird gaps in someone's logic or the specific way they see the world.
Psychologists like Arthur Aron have spent decades researching this. You’ve probably heard of his "36 Questions That Lead to Love" study. It wasn't actually about magic or Cupid; it was about "sustained, escalating, reciprocal, personal self-disclosure." Basically, you tell me something scary, I tell you something scary, and suddenly we aren't strangers anymore. But you can't just drop a "What's your biggest regret?" on the guy sitting next to you at a bar without it being incredibly awkward.
Context matters. So does timing.
The psychology of why "What do you do?" fails
We ask about jobs because it's safe. It’s an easy category. But according to Dr. Elizabeth Dunn, a professor of psychology at the University of British Columbia, talking about "stuff" or "status" doesn't provide the same hit of dopamine as talking about experiences or values. When you ask a person about their job, they pivot into "professional mode." They give you the rehearsed pitch. You aren't meeting them; you're meeting their corporate avatar.
Try shifting the focus. Instead of the job title, ask, "What’s a problem you’re currently trying to solve?"
This works because it reveals their intellectual curiosity. It shows you what they value. Maybe they’re trying to fix a bug in some code, or maybe they’re trying to figure out how to get their toddler to eat broccoli. Either way, you're getting a glimpse into their daily reality. It’s much more visceral.
Finding the right question to ask to get to know someone in a casual setting
You're at a party. Music is loud. You don't want to get philosophical yet. You just want to see if this person is worth more than five minutes of your time.
I’ve found that the best questions are slightly "left of center." They catch people off guard in a fun way. For instance, ask someone: "What is the most niche thing you are a 'super-fan' of?"
Everyone has one.
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Maybe it’s 1990s Japanese stationery. Maybe it’s a specific era of Formula 1 racing. When people talk about their hyper-fixations, their face changes. Their pupils dilate. They stop performing and start sharing. That’s the "get to know you" sweet spot.
Another great one is asking about their "anti-bucket list." We all know what people want to do—visit Paris, skydive, whatever. But what will they never do again? Did they try oysters and hate them? Did they go to a silent retreat and find it pretentious? The things we reject define us just as much as the things we chase.
Deepening the bond: The "Values" phase
Once you’ve moved past the surface, you need meatier questions. This is where you look for alignment. You aren't just looking for facts; you're looking for their "operating system."
A favorite of mine is: "What’s a belief you’ve completely changed your mind about in the last three years?"
This is a high-level question to ask to get to know someone because it tests two things: intellectual humility and growth. If someone says, "I've never changed my mind," that’s a red flag. It means they're stagnant. If they tell you a story about how they used to be judgmental about a certain lifestyle but now see it differently, you’ve just learned a ton about their capacity for empathy.
Why vulnerability is a two-way street
You can't just be an interrogator. If you ask a heavy question, you have to be ready to answer it too.
Social penetration theory, developed by psychologists Irwin Altman and Dalmas Taylor, suggests that relationships develop through a process of "peeling back the onion." If you peel a layer off them, you better peel one off yourself. Otherwise, it feels like a police interview.
If you ask, "What's a fear you're currently working through?" and they answer, you need to follow up with your own. "Yeah, I get that. Personally, I'm terrified of [X]." This creates a safe container for the conversation to stay deep.
The "Day-to-Day" Reality
Sometimes we get too caught up in the "big" questions. We ask about dreams and fears, but we forget to ask about how they actually live.
- What does your ideal Tuesday morning look like?
- What’s the last thing you read or watched that actually made you think?
- What’s a "small win" you had today?
These are low-stakes but high-reward. They give you a sense of their rhythm. You learn if they’re a chaotic morning person or a slow-burning night owl.
What to avoid (The "Vibe Killers")
There are certain questions that feel like you’re reading from a "How to Network" book from 1985. Avoid these.
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"Where do you see yourself in five years?"
Nobody knows. It’s a job interview question. It makes people feel pressured to sound ambitious or stable. It’s not a conversation; it’s a test.
"If you could have dinner with anyone, dead or alive..."
It’s been asked a billion times. Most people give a standard answer like "Nelson Mandela" or "My Grandma." It doesn't tell you anything new.
Instead, try: "If you had to give a 20-minute presentation on something with zero preparation, what would it be?"
The Nuance of Cultural Backgrounds
It’s worth noting that "getting to know someone" looks different across cultures. In some high-context cultures, asking direct personal questions right away is seen as incredibly rude or invasive. In those cases, the best question to ask to get to know someone might actually be a question about their community or their family’s history rather than their individual "inner child."
You have to read the room. If someone is giving one-word answers, they aren't being difficult; they might just have different boundaries.
Actionable Steps for Your Next Conversation
Stop overthinking it. You don't need a list of fifty prompts. You just need curiosity.
- Listen for the "Nouns": When someone is talking, listen for the specific things they mention. If they say, "I went to the park with my dog," don't just say "Cool." Ask, "What kind of dog?" or "Is that park your favorite spot to think?" Follow the breadcrumbs.
- The "Why" Pivot: When someone tells you what they did, ask why they chose to do it. The "what" is the data; the "why" is the soul.
- Use the "Rule of Three": In any new conversation, try to get three layers deep on one topic rather than touching on ten different topics superficially.
- The "Advice" Strategy: People love feeling useful. Ask, "I’m looking for a new [book/podcast/habit/restaurant]—what’s something you’ve discovered recently that actually changed your routine?"
Real intimacy isn't about having a perfect list of queries. It’s about being present enough to notice when someone leaves a door cracked open and having the courage to walk through it. Next time you're meeting someone new, leave the "What do you do?" in the car. Ask them what they're obsessed with instead. You'll be surprised how fast the walls come down.
Next Steps for Mastery
To truly improve your conversational depth, start by practicing the "Observation-Question" technique. Instead of a random prompt, observe something about the person's current state—an accessory they're wearing, the way they reacted to a joke, or even the drink they ordered—and ask a "why" question based on that observation. This proves you are paying attention, which is the highest form of flattery and the fastest way to build trust.