17 questions to ask someone if you really want to get to know them as a person

Are you tired of small talk and really want to know someone as a person? Great! 

There are many, many questions you can ask someone to really get to know them. In this article, we’re focusing on the best ones. 

1) How do you like to spend your free time?

I never ask people what they do for a living. For many years I was “trapped” at a gas station dreaming of better opportunities and hating every minute of it. 

For me, a better question to ask is how they spend their free time. If they’re not a super-busy parent of small kids, their answers will reveal a lot about them.

You’ll get to know their hobbies, interests, and passions. Who knows, maybe you have more in common than you first thought. 

2) What is your favorite book/movie/TV show, and why?

The same goes for this question. Chances are, you have a favorite TV show or movie in common.  

You’ll find out if they like comedies, action movies, dramas, documentaries, or biopics. 

Expanding on this question allows you to delve deeper into their personal experiences and emotions associated with their favorites.

Plus, you’ll get new recommendations. 

3) What are your aspirations or goals?

I already said I don’t ask people directly what they do for a living. It’s better to ask them about their goals, dreams, and aspirations. 

This will reveal much more about them, and you’ll get to know them more as a person.

4) Can you describe a significant life event that shaped who you are today?

When someone shares a significant life event that has shaped who they are today, it opens up an opportunity for you to understand their personal growth, resilience, and the impact that experience had on their life.

5) What is your favorite travel destination, and why?

I love talking about travel and the different locations people visited. It doesn’t even have to be anywhere exotic. 

You’ll learn what they cherish about life by discovering their favorite destination. If it’s Ibiza, they love partying. If it’s the Maldives, they love relaxing. And if their favorite travel destination is a national park, you’ll know they’re outdoorsy. 

6) Do you feel deeply passionate about any specific causes or issues, and why?

Many people care deeply about a number of issues. They’re often drawn to certain causes or issues due to personal experiences, empathy for others, or a desire to positively impact the world. 

By exploring their passions, you’ll better understand their concerns, values, and how they actively engage in creating change.

7) What are you currently learning or trying to improve upon?

Personal growth and continuous learning are important parts of self-improvement. Asking someone about what they’re currently learning or trying to improve in their lives or society provides insight into their curiosity, aspirations, and dedication to self-development.

8) What is your favorite way to challenge yourself or step out of your comfort zone?

I love this question. 

If they love stepping out of their comfort zone, they’ll share what they respect or fear. If they never challenge themselves, you will put a bug in their ear that will perhaps encourage them to do so. 

9) Do you have any role models or people who inspire you?

When asking someone about people who inspire them, you have an opportunity to learn about the individuals they admire and the qualities or achievements that resonate with them.

If someone tells you they admire Donald Trump, you’ll know where they stand on many issues. The same goes if their role model is LeBron James, Emma Watson, or Greta Thunberg, for instance. 

By knowing who their role model is, you’ll learn about their values.

10) How do you handle stress or difficult situations?

Stress is a major factor in many people’s lives. There’s almost no escaping it these days. If you aren’t stressed out at work, then reading the news or social media will stress you out. 

By getting an answer to this question, you will learn how they cope with pressure and may learn some new stress relief techniques you could implement in your life too. 

11) What are some of your favorite childhood memories?

Favorite childhood memories are unique to each person, shaped by their experiences, family dynamics, and personal interests. 

They hold a special place in our hearts, reminding us of a time when life was simpler, curiosity was boundless, and the world was full of wonder.

By asking this intriguing question, you’re sending the person you’d like to know more down memory lane.

12) Are you more of a planner, or do you prefer to go with the flow?

With this question, you’ll get to know how impulsive or even fun they can be. You see, people have different preferences for planning their activities. 

Some schedule a whole month in advance, while others are more laid back and go with the flow.

Whatever their answer is, know that it’s based on their personality, experiences, and preferences. 

Understanding their choices gives you an understanding of how they go through uncertainties, make selections, and react to random or unexpected situations.

13)  What are your favorite types of music, and why do you enjoy them?

Music is a powerful way for people to express themselves, connect with others, and even improve their lives.

We all have different tastes in music. I, for example, like rock and punk-rock. Others love hip-hop or classical. 

The reason we enjoy certain types of music is personal. It’s based on emotions, memories, lyrics, melodies, instruments, cultural influences, and more. 

Once you learn their favorite music type, you can spark conversations that can lead to shared experiences or recommendations for new music.

14) How do you express yourself creatively (e.g., painting, writing, dancing)?

Look, I get it. Some people don’t have a creative bone in their body. However, you’d be surprised how many people like to sing, paint, dance, or use other forms of creative expression.

Again, with this question, you’ll find out many things that were previously kept locked. 

15) How do you define success, and what does it mean to you?

For some, success is exclusively tied to money. For others, it’s family and friends. What they answer will reveal a lot about them.  

16) Is there a special experience or achievement you’re most proud of?

This question invites them to reflect on a significant and powerful moment in their life that brought them a sense of achievement or fulfillment. 

We all have moments that stand out as particularly meaningful or worthy of pride.

It could be graduating from school or university, receiving a promotion, launching a successful business, recovering from a physical or mental health setback, publishing a book, making a positive impact in the community, etc.

Can you see now how this question can be powerful in revealing their closely-guarded cards? 

17) What does your perfect day look like?

You can start this question by sharing what yours would look like. But “a perfect day” is such a subjective concept that it varies greatly from person to person based on their interests, priorities, and preferences. 

And that’s why asking this question is so important. 

It represents a day when everything aligns to create an ideal experience, leaving you feeling happy, inspired, and deeply satisfied. 

While we all have a perfect day that may be unique, there are some common elements that contribute to its idyllic image.

Final thoughts

I hope this article left you inspired with questions to ask someone if you really want to get to know them as a person. 

It really isn’t that difficult. Just listen actively and ask interesting follow-up questions to get to know them even deeper.