Creative Questions to Ask Someone

Creative Questions to Ask Someone

4 min


“Asking good questions is productive, positive, creative, and can get us what we want.” Most people believe this and yet some do not ask enough good questions. Perhaps one of the reasons for this is that effective questioning requires a great listener.

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Effective Questions are:

  • Questions that are useful and thought-provoking.
  • Open-ended and not leading questions.
  • They are not “why” questions, but rather “what” or “how” questions. “Why” questions are good for soliciting information but can make people defensive so be thoughtful in your use of them.

Creative Questions: Ask to Know Someone

These questions are powerful on their own, but I do have a few guides to help you get the most out of them. When asking effective questions, it is important to wait for the answer and not provide the answer. Many of these questions will bring up sensitivity that might touch on their fears, missed opportunities, and compassion.

If you had to choose to live without one of your five senses, which one would you give up?

Which of the five senses could they live without? If someone is touchy-feely, they’d most certainly leave touch intact. If they left out their eyes, then you know they are not into physical things. If they cut their sense of taste out, then you know they aren’t picky about where to eat.

What animal best represents you and why?

This is one of those good questions to get to know someone and a great way to understand how they see themselves. Like the king of the jungle the lion, or do they reflect more personable qualities, like the loyalty of dogs?

Where do you see yourself in five years?


This is one of the greatest questions to get to know someone because while it comes off as a simple conversation starter, their answer will often reveal what’s most important to them. Do they respond with something work-related (I’ll be a business owner)? Family-related (I’ll be married with my first child)?

Why did you choose your profession?

Stop asking someone, “Where do you work?” Instead, try to know if they’re driven by the money, passion, a series of coincidences, or family by asking why they chose their profession. The answer will give you an insight into their motivations for success.

How do you want to be remembered?

This is one of the most interesting questions to ask as it’s self-reflective and opens up a conversation about a person’s impact on others. It will give you an insight into their ideas, morals, and values. Do they want to be remembered as a family man, as a good friend, and etc?

In what ways are you a leader? In what ways are you a follower?

This two-part question is an introspective look into someone’s motivations. You can find out if they are an introvert, an extrovert, or something in-between.

What would be your “perfect” day?

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Most people will look to their past to find an answer to this question. Some have already lived their perfect day and would love to recreate it. You’ll learn who and what is most important to them.

What makes you happiest?

This question is ambiguous enough to be a great question to ask on a first date, a solid interview question, or one of the more introspective conversation starters to use with friends, family, or acquaintances.  Since happiness is universal, and what makes someone happy is so personal, it can help you quickly get to know someone.

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Who’s your personal hero?

Ask someone when you’re trying to get them to open up. We often emulate our heroes and hold their values up as a template for our own. This question will give you a deeper understanding of someone’s personal values and beliefs.

What’s something too serious to be joked about?

Everyone has a limit to what they find funny. This question is a great way to get people to open up and reveal their stance on sexist jokes, dark humor, etc.

What’s your favorite holiday and why?

The holidays always bring the strongest emotions and create the most treasured memories.

While it seems like this question won’t help you get to know someone, it actually reveals a lot about their culture, beliefs, and family ties. What type of person are they? Will they choose Thanksgiving (family oriented)… or New Year’s Eve (party/celebration oriented)?

What’s the craziest thing you’ve ever done?


This is a fun question to ask and will introduce you to a person’s wilder side. Their “craziest” is traveling out of the country, hiking a mountain, or dating someone? Since people love to recount their adventurous moments, this question almost always leads to a fun, engaging conversation.

If you could have the answer to any question, what would that question be?

This is one of the best questions to ask when you’re trying to get someone to open up.

It gives anyone the space to talk about the biggest unanswered question they have about their past, present, or future. Their response is very likely going to be something deeply personal. Be prepared to be supportive and to respond with your own answer to the question.

What are you most grateful for?

This is one of the most classic questions to ask someone. On the surface, it seems like the response won’t be revealing, but their answer will tell you exactly what’s most important to them.

Are they most grateful for their family? Their health? The roof over their head?

These open-ended questions will give other people the opportunity to share their stories, experiences, hopes, and dreams. If you’re looking to get to know someone on a deeper, more meaningful level, start with one of these great questions to ask. Comment below with your favorites and any other great questions to ask people!

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Renz Simpao

Hello, I'm Renz Simpao, an Educator, Blogger, and Freelance Digital Marketer who helps different brands to achieve their aim goals with a combined experience of 8 years in B2C, program development, and course training.


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