People Who Think You're Really Cool Almost Always Ask These 11 Questions When They Talk To You

Written on Feb 13, 2026

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For people who want to get to know someone else and also leave a good, lasting impression, they usually try to be extra curious and ask questions. Their curiosity isn't coming from a place of trying to be nosy at all. Instead, they're just naturally intrigued and want to find a way to better understand what makes you, you. These are usually the type of people who notice the little details about others that might usually get overlooked. People who think you're really cool almost always ask certain questions when they talk to you because they want to learn from you and connect, too.

Studies have suggested that questions are often the best and most useful tool to give us information and improve the interactions that we have with other people. It's always nice when you're talking to someone and they suddenly ask you such a thoughtful question about yourself that really makes you think. You feel even closer to them because you can tell they genuinely want to know you. Most of the time, these individuals don't even realize they're being probing as they are because to them, it's just something they do unconsciously.

People who think you're really cool almost always ask these 11 questions when they talk to you

1. 'Who or what inspires you?'

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When someone asks this question, it shows that they want to know the people or experiences that fuel your drive because it can give them an insight into your values. They're able to connect on a much deeper level than just superficial conversation. 

The question also gives you a chance to show what really matters to you. It's less about bragging and more about sharing these small glimpses into your passions. "Being passionate about something or someone feels good; it gives life meaning and enhances our vitality, making each day a little more exciting," explained researcher and educator Anna Sverdlik.

You can talk about the third grade teacher that inspired you to pursue your creative passions or your favorite artist that encapsulates what's important to you. People who are asking this question are truly trying to see behind your personality and what makes you move emotionally. 

People are usually naturally curious about the things that drive someone else's determination. Being able to share those details helps people understand just how your mind works.

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2. 'How did you get so good at your skills?'

businessman asking colleague how they got so good at their skills in work meeting JLco Julia Amaral | Shutterstock

People who think you're really cool almost always ask how you got good at your skills when they talk to you, because they're trying to understand the effort and practice that goes into the talents you have. They're not just trying to admire the end result, they want to know your process and are curious about how you might've reached your success. 

You're being given the platform to talk about your journey, and by that result, you can share your struggles and even the mistakes that you might have made along the way. As neuropsychologist Sam Goldstein pointed out, "Mistakes are not a reflection of moral failure; they are a source of information. The most successful people in any field view errors as feedback, not condemnation."

People truly enjoy hearing about the less talked about aspects of someone's process. It makes that person feel way more relatable. It's just inspiring to see and talk to someone who's really good at something and understand that it didn't really happen overnight. When you're opening up about your process, it shows that skill is rooted in growth, not just talent.

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3. 'What's your go-to comfort food?'

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People are usually asking this question from a place of wanting to know what makes you feel safe. When you're having a bad day, what's the kind of meal that you're either cooking or ordering in help soothe your stress levels? Comfort foods almost always come with a story attached as well.

Even if it's something basic, there's usually feeling tied to it. Being able to share that story with someone often makes a conversation feel much more humane and even warm. Having a specific food that you lean on in the moments you need it can also tell a lot about your personality. It shows how you unwind, and there's really no right or wrong answer.

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4. 'What's your favorite way to spend a weekend?'

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It might seem like a question that's surface-level, but they're actually trying to get a glimpse into your lifestyle. They want to know about your hobbies and interests on the weekend because it's usually when most people have free time. 

Weekends are quite personal. It shows how someone recharges after having a busy, stressful week. By asking this, they're curious about your vibe and what kind of energy you have when there aren't deadlines and appointments to adhere to.

"Being interested is strategic. Curious people make better collaborators, better partners, and better leaders. Why? Because they don’t assume they already have the answers. They go in open. They ask instead of tell," Goldstein pointed out.

Sharing the details of how you spend your weekend, whether you're at home catching up on the shows you've missed or going out into the world to try new restaurants and spend the two days shopping and exploring, it says a lot about you. Talking about what you do on the weekends can even open up conversations about much deeper things, and you can find common ground with the person asking you.

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5. 'Do you have a favorite weird habit?'

woman at home thinking about her favorite weird habit JLco Julia Amaral | Shutterstock

Whether it's about a strange habit you love or a wacky ritual you do every day, people who think you're really cool almost always ask these questions when they talk to you. When getting to know you, people aren't just wanting to see the perfect version of you; rather, they want to know about your quirks when no one is looking. 

Maybe you're the type of person that has full-blown conversations with yourself or you can't fall asleep at night without putting on episodes of your favorite show. Whatever the case may be, opening up about these weird habits can help someone learn more about you. 

They're able to see past the "cool" persona that you have, and because of that, they're able to relate more to you. Sharing them also shows just how self-aware you are, and also how confident you are about these odd habits too.

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6. 'Have you always been this way?'

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This question is often rooted in knowing about someone's personal growth and the experience that shaped just how cool they are. They're not asking from a place of trying to be rude, they're asking because they can sense there's some lore to your life. 

A lot of the time, they can't imagine you having an awkward phase or being unsure about yourself. The confidence you have now feels to them as if it's something you've always had. "The foundation of genuine confidence isn't built on praise or quick wins. It's built on effort that's earned and thus internalized," suggested psychotherapist Keven Duffy.

But even for the most composed person, their confidence wasn't something they got overnight. By being asked this question, it allows you to show that you've not always been comfortable in your skin and with yourself. But, through growth and challenging yourself, you've become the person you are today. 

People truly enjoy hearing about the transition from who someone was to who they are now. They enjoy hearing about the journey and all of the moments that built up their confidence. It's inspiring.

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7. 'What's the last thing that made you laugh uncontrollably?'

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People want to know how you feel joy in the most mundane of moments. Talking about the things that have made you laugh recently can inform someone about what cracks you up and also what you find not to be funny at all. 

Sense of humor is so subjective to the individual, and being able to learn about someone's own way of joking can tell a lot about them. It's also a question that can really lighten the mood. Just thinking about the moment usually ends up bringing a smile to your face or you just start laughing all over again. 

It might have been a dumb joke, but in the moment, it truly tickled you. People who think you're cool usually want to see your silly side as well as your confident and secure side.

RELATED: People Who Think At A Genius Level Almost Always Ask These 11 Questions When They Talk To You

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8. 'How do you stay calm in situations?'

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When people find you calm, cool, and collected, they're usually admiring the fact that you have this ability to handle pressure effortlessly. To them, it seems like nothing can shake you and they want to learn your approach. 

Most people assume that that level of calm is just something you've mastered without any effort. But, in reality, it's come from so many experiences where you might've blown your lid and reacted too impulsively.

You've been through enough chaos to know that panicking rarely helps. The calm energy that you have now was earned. When you're able to explain how you maintain your composure, you come of as being loads more relatable compared to having this mysterious aura around you. 

You might stay calm because you've learned specific habits that help you pause before reacting. Even just sharing that with other people can help them learn how to navigate high-pressure situations.

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9. 'What's the most fun thing you've ever done?'

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Hearing about someone's adventures and the experiences they've embarked on can be entertaining to listen to. By talking about what makes life exciting for you and even the risks that you've taken, it helps someone else get to know you better. 

You also can't answer without replaying the moment in your head. The memories that you're talking about usually come with emotion attached because you most likely had a time and found joy in being able to break away from your usual routine.

"Whether navigating the rapids of a river, exploring a new culture, or undertaking a creative endeavor, each adventure carries the potential to reshape our perspectives, bolster our mental fortitude, and add a vibrant layer to the tapestry of our lives," psychologist Mike Rucker said.

For some people, the most fun thing they've ever done might have been simple, but in the moment it was truly everything. It doesn't have to be the most extravagant adventure, but as long as it's personal and full of good memories to look back on, that's what really matters. 

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10. 'Do you usually remember your dreams?'

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Someone is usually asking less about sleeping habits and are actually more curious about the way your mind might wander when you're dreaming. Dreams usually have a lot to say and can tell quite a bit about a person's waking life. You simply can't answer this question without thinking for a second as well because dreams can be quite slippery to recollect.

Some people are also really good at being able to remember their dreams, but whether you're able to remember instantly or it takes some time to muddle through the fragments, it still says something about that person's imagination. People who are asking this are usually fascinated by the fact that dreams are usually an entire experience out of your control. It adds another layer into how intriguing you are to them.

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11. 'How do you handle failure?'

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People who think you're really cool almost always ask questions about how you handle failure, because asking how a person deals with moments of setbacks can reveal a lot about their mannerisms and habits. While you may appear strong and cool to them, they're also interested in the moments where things may not have gone your way. They're curious about how you picked yourself up after all of that.

"The odds of making a mistake on any given day are high, considering every decision we make has the potential for error. Mistakes are an inevitable part of life. Rather than holding ourselves to excessive standards, wallowing in regret, and tearing ourselves down when we screw up, perhaps we can learn to stop dwelling and start living," said clinical mental health counselor Raychelle Cassada Lohmann.

They're probably hoping that your answer will provide some kind of reassurance for how they should act in the face of mistakes and rejection. Hearing that you're someone who doesn't let failure get the best of you can be quite encouraging. 

Whether we like it or not, it's inevitable that you'll make a mistake in life. Things may not go your way and that's fine, because it's all part of the process.

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Nia Tipton is a staff writer with a bachelor’s degree in creative writing and journalism who covers news and lifestyle topics that focus on psychology, relationships, and the human experience.

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