According to the bestseller How to Win Friends and Influence People, the key is to show a genuine interest in others. Sure, some might think you’re weird for asking something random out of nowhere.

However, the majority love talking about themselves! If you’re an introvert, making inquiries takes the pressure off you to share. If you’re an extrovert, engaging this way shifts the spotlight onto someone else.  

Make Connections with Random Questions 

Enjoy making connections by reaching out to your lifelong best friend, distant cousin, fiancé, or a complete stranger with these random questions to ask. Strike up a casual conversation while you’re stuck in a long line. Spice up those family holiday dinners by asking for odd tidbits your loved one is excited to share. Let’s look at a variety of things we can ask and what the answers can reveal.   

Mental Revelations 

Expanding our minds and skills is something that happens as a natural part of living our lives. Then there are times we make concerted efforts to pursue new passions. What do you keep telling yourself that you should learn? The answer can be a new language, athletic feat, musical ability, unusual art, or maybe the skills of meditation, productivity, or humility. Any reply will provide a peek into their thoughts. 

It’s a wonder as to why we’re fond of specific experiences. We understand how we feel rejuvenated visiting and cherishing a particular place or enjoying our top pick meals.

Now take a further step with this weird query. If you are designing a stamp celebrating anything or anyone, what would you choose? You’ll discover things your friend appreciates that you’re also fond of or are unique to them. 

Logically we understand that we’re far from perfect. However, keep in mind that you do offer much to the world exactly as you are. What three specific things have you done that make you proud? Moments or achievements where it seems close to bragging if you just started expounding, but it’s not boasting because I’m asking you to share. Be ready to listen to their reply!    

Physical Clues 

Interactions via social media (and often life in general) can be superficial, but most of us know we have more to offer. That said, the first thing many observe when we present ourselves to the world is our physical appearance. If you wake up tomorrow with a physical change that has to do with appearance rather than health, what would you want to be different? 

Besides the typically appreciated, classic life highlights (friends, family, pets, health, financial security, and such), what are the top three items or experiences society deems unnecessary that you could hardly live without having?

A monthly massage and noise-canceling headphones are a gift of sanity for some amidst a busy existence. I adore white-out correction tape and line divider stanchions because they provide a sense of control in the surrounding chaos.   

Emotional Insight 

Directly sharing our vulnerabilities is not an appealing thought, but answering a somewhat strange question can expose them. If you could have any superpower, which would it be and why? Those who feel overwhelmed with their “to do” list would find having control over time appealing. You may expose the fact that you love your pet more than most humans if your superpower wish is to talk to animals. 

Sharing a new box of Crayola crayons brings kids together. As time passes, the ubiquitous crayon continues to connect a rainbow of personalities. While a considerable amount of further color psychology research needs to happen in this area, there are some emotional state assumptions while interpreting color preferences.

For example, yellow could be the reflected color of a sunny disposition. Say you were a crayon, what color would you be? 

We can all celebrate exciting and comforting little moments! Perhaps making a perfect chocolate milkshake or waking up five minutes before your annoying alarm can surprise you. It can be a hummingbird flying past your window or your favorite song playing on the radio when your car starts. What little things have happened this week that gave you a somewhat disproportionate level of joy?   

Spiritual Epiphanies 

Whether an individual is religious or not, the appreciation of unexpected kindness is universal. Do you have a story of someone you just met doing something kind for you? A stranger helps you change a tire or a small gesture like a cashier giving you a free coffee because your wallet is still at home. Their reply gives you a glimpse into an impactful moment. 

You might not describe yourself as spiritual or superstitious. Or you are very religious, admiring faith above everything and not minding if you walk under a ladder or step on a crack. Wherever you fall on that spectrum, this is still an enjoyable question. Do you wish on falling stars or birthday candles? Have any of those wishes come true?  

The Inside the Actor’s Studio television show features interviews by James Lipton that always conclude with a set of intriguing questions. One of those touches on the spiritual side. If heaven exists, what would you expect to hear God say when you arrive? Even though politics and religion are often taboo in casual conversation, this question is light enough while still offering the chance for a meaningful answer.   

Relationship and Career Discoveries  

What we admire in those around us reveals a lot about ourselves. Loyalty, creativity, understanding, honesty, optimism, and confidence are traits that could encourage us to connect. What characteristic does your best friend have that you like best? Their answer may help you find a kindred spirit or learn how to be a better friend. 

Discover more admirable traits with further random questions. Which cartoon character is your favorite? Which is a lot like you? Answers to each question are often very different from one another! Those features intriguing to us can be the opposite of what we possess. To give an example from the Pooh Bear stories, Rabbit and his always-stressing tendencies can appreciate the need for some Tigger-like charm in his life. 

As a child, what did you say to the question, “What do you want to be when you grow up?” We’re talking very young before you understood the meaning. Admittedly, I told everyone I wanted to be a lion. My first day performing as a Disney World character was as Prince John, the lion in Robin Hood. So yes, even silly childhood dreams can come true.   

Random Questions are Fun  

You can stick to the typical inquiries asking where someone is from or what their favorite color, food, or holiday is. Or you can stand out from the crowd and consider what you’re interested in knowing. Are you curious to discover people’s passions, beliefs, or goals? Are you wondering what makes them smile and what is meaningful to them?  

Whether you’re on a sports team or prefer multiplayer video games, attend the same class or share an office, visit an in-law only on Christmas or see a cashier daily at Starbucks, you’re often physically or virtually within reach of another person. Random questions can be your method of bonding with your inner circle or a way to help that inner circle grow. So reach out and ask anyone anything!