10 Questions to Ask to Truly Get to Know Someone
By: Brian Kim
Tags: Questions, Conversations, Interactions, Social

Photography: Pexel Images

Way back when I was a college student, I experienced something almost everyone in this world can relate to: I met people. A lot of them. Being part of a social fraternity (for two years) and a professional business fraternity, I was required to have thirty minute individual meetings with the new members every semester. I remember the first year or two was absolutely thrilling; I loved getting to know all these unique characters. But after a while, I had exhausted my fake interest in response to the questions “where are you from?”, “what’s your major?”, and “what do you like to do?” I wanted to engage in genuine conversations, leap from exciting topic to exciting topic, and stray away from awkward silences.

That’s when I started asking more interesting questions- questions that would raise eyebrows and elicit responses like “oh! That’s a good question.” Thirty minute mandatory meetings became one hour memorable introductions. I was no longer remembering faces and names; I was remembering experiences and moments.

Today, I want to share those questions with you. I guess you could say I embarked on a social experiment for the past few years, observing responses with various questions that I had come up with. Might I add that these questions do not have to be exclusively in a professional setting with someone new. I found that whether I was playing golf with some old high school friends, getting lunch with my new co-worker, or trying to impress a girl on a date, these questions ignited excellent conversations that I can still clearly recall to this day.

In a nutshell, the questions are:

What were you like in high school? And college? What are you like now? If you changed, was it on purpose? What is your biggest pet peeve? If you could visit anywhere in the world right now, where would you go and why? Do you have any famous celebrity interactions? What are your parents’ stories? Where do you see yourself in 5 years? 10 years? If money didn’t matter what occupation would you have? What was the peak and pit of this past year? If you had a free Saturday, what would you be doing? How do you define success? Do you want to be successful one day? If so, how?

You could stop reading at this point. Take a few of these questions with you the next time you meet up with someone and see the difference. If you want my analysis of the questions and some example answers, read on.

What were you like in high school? And college? What are you like now? If you changed, was it on purpose?

This is, hands down, my favorite question and I always ask it first. One of the more fascinating stories to hear about someone is how they have grown over the years. It puts them in a nice light because usually people learn to be better in the next chapter of their life. I also think reflection is extremely important; how can you become a better person if you don’t recognize your past mistakes? The last question is completely up to you. Personally, I like to ask if the change was on purpose because I changed on purpose.

2. What is your biggest pet peeve?

If there’s something that people can talk about forever, it’s something that they hate. I have had many hilarious and serious responses to this question, all with great back stories. My greatest pet peeve? People that pretend to be someone that they aren’t. I value genuine interactions, and it really grinds my gears to see someone that fakes who they really are. Just be you.

3. If you could visit anywhere in the world right now, where would you go and why?

This tends to be one of my more popular questions, especially with the younger population. I think at our age, traveling is on most people’s bucket list and we love talking about the places we have visited/want to visit.

4. Do you have any famous celebrity interactions?

I like this question because it’s different and fun. Believe it or not, you can learn a lot about a person from this question. Most of the time, these celebrity interactions can tell you about their hometown, their hobbies, or the places they have visited. For instance, I always say two celebrity interactions. One happened this past year. My friends and I had recently got into core power yoga, and one day opened the studio door to Malia Obama talking with the front desk. That’s right, I did yoga with Malia Obama (spoiler alert- she’s as tall as I am, which is 6'1). My second happened back in the 8th grade. My best friend’s father was the president of a hotel, so we would go work out there every once in while. We casually pulled up one Saturday, and some of the Miami Heat basketball team was at the gym. Turns out Lebron James had his secret wedding there. So we worked out with Chris Bosh and other players on the Heat. I thought it was super funny that Chris Bosh would cuss every time he lifted- every time he did a bicep curl he would grunt “F*ck!”, “sh*t!”, or “b*tch!”.

5. What are your parents’ stories?

In other words, where were your parents born? Where did they grow up? How did they meet? What do they do now? etc. I think we take for granted how important our parents are in shaping our lives. For our first two decades, they shaped us to be whatever they envisioned us to be. We might have wandered from that path now, but the foundations of our livelihood are built upon our parents’ will. This is a very humbling question, and I have heard some of the most inspiring stories about parents starting from nothing.

6. Where do you see yourself in 5 years? 10 years?

This is a classic interview question. A career is arguably our identity- we will have spent most of our life at work (other than sleeping). I like to see what a person’s goals and visions are. However, I also pry into things outside just the career aspect. Where are you going to be? Do you have a family? What are you doing outside of work?

7. If money didn’t matter what occupation would you have?

Incredibly, almost every person I have asked this question has said a different occupation than the one they are pursuing. It’s so interesting to hear what people answer, because it gives insight into their hobbies and past times. For me, I would be a head chef by day and a DJ by night. I am a people pleaser, so I love seeing people enjoy my food and my music.

8. What was the peak and pit of this past year?

I stole this question from my sister. Whenever I would go on a trip or finish a project, she would ask me what the peak and pit were. It honestly is a great way to get the short but efficient version of a longer story. Like I said before, reflection is critical to understanding our future, which is why I love this question.

9. If you had a free Saturday, what would you be doing?

This was actually the first question I was asked freshman year of college. I thought it was a clever alternative to “so, what do you like to do?” but I realized it was also a way to see how driven the individual was. Is the day packed? Or are you just watching Netflix all day? I think this question can tell you a lot about a person’s work ethic.

10. How do you define success? Do you want to be successful one day? If so, how?

This is definitely one of the more difficult questions to answer because it is so open ended. But I think that is also the beauty of it; you will never get the same response twice.

Honorable mentions:

11. What do you think are the qualities that make a person attractive?

12. What is one thing you see wrong in the world and how would you change it?