Getting to know someone should go beyond the simple “what’s your favourite colour?” And these 17 questions are designed to encourage conversations that are more meaningful and fun.
What’s the Story Behind Your Name?
Names carry meaning, history, and often a good story, and some are passed down through generations, representing family traditions, while others are chosen because they sound beautiful or hold special significance to a parent. Asking someone about their name can lead to delightful discoveries, like learning about a grandparent they were named after or an unexpected connection.
What’s a Memory That Always Makes You Smile?
Everyone has a memory that lights up their face whenever they think about it. Maybe it’s a childhood adventure involving mud puddles and mischief, or a recent experience like a surprise visit from an old friend; when you ask someone about these moments, you’re inviting them to relive something positive.
If You Could Live Anywhere in the World, Where Would It Be?
It’s a fun way to imagine different lifestyles together while learning about their aspirations and the environment where they feel most alive, because dreaming about an ideal place to live often reveals more than just travel preferences. Someone might describe a peaceful village in the English countryside where the air smells like fresh rain or a busy city like London.
Who Has Had the Biggest Impact on Your Life?
Influential people shape who we are, and their lessons often stay with us forever, therefore asking this question is a thoughtful way to learn about the values and qualities someone admires most. Whether they talk about a patient teacher who believed in them or a parent who sacrificed so much, their answer can be deeply personal.
What’s a Skill You’ve Always Wanted to Learn?
Learning something new can feel like unlocking a hidden part of yourself, can’t it? When you ask someone about a skill they’ve always dreamed of mastering, it opens up a window into their hidden interests and ambitions, and it might even represent a new chapter in their life.
What Does Your Perfect Day Look Like?
A perfect day says a lot about a person. Some people might picture a leisurely morning with a cup of tea and a favorite book, while others imagine an action-packed day exploring new places with loved ones, while their answer could reveal the small pleasures they cherish or the bigger dreams they hold for their ideal life.
What’s a Food You Could Eat Every Day Without Getting Bored?
Food is about more than taste—it’s about experiences and memories, so this question is an easy way to bond over something we all love. Asking someone about their ultimate comfort food or an everyday favorite can lead to laughter, nostalgia, and even surprising stories, like a dish that reminds them of family.
What’s the Best Book or Film You’ve Ever Experienced?
When someone shares their all-time favorite book or film, you’re getting a glimpse into what moves them emotionally or intellectually, especially if it’s a novel that left them in tears. They will show you the kinds of stories and themes that resonate with them—and it’s also a great way to discover something new for your own list.
If You Won the Lottery, What’s the First Thing You’d Do?
This question is always a crowd-pleaser because it’s fun to dream big, and the response can commonly reveal someone’s priorities and what they value most. Would they buy a cozy house near the seaside, take their family on a luxurious holiday, or invest in a cause close to their heart, perhaps?
What’s One Thing You’ve Done That You’re Proud Of?
Pride can be found in the small but meaningful milestones that shape us, therefore when you ask someone about what they’re proud of, you’re giving them a chance to celebrate themselves. This could be them overcoming a fear or achieving a personal goal.
What’s the Best Advice You’ve Ever Received?
Whether it’s a reminder to stay true to themselves or a practical tip that changed their outlook, their answer provides insight into the lessons they hold closest, not to mention that good advice can stick with us forever. It shapes the way we approach life’s challenges and opportunities.
How Do You Usually Spend Your Weekends?
Weekends are when people let loose and focus on what they love most. Asking this gives you a glimpse into their world—whether they’re all about outdoor adventures or lazy mornings with Netflix—or both. It’s an easy way to understand their hobbies and how they like to unwind, which can help you find common ground, too.
What’s a Quirk About You That Most People Don’t Know?
Quirks are what make us interesting and unique, and sharing them often leads to lighthearted and enjoyable conversations, so maybe they have an unusual knack for remembering trivia, perhaps. Encourage them to share something fun about themselves that might not come up in everyday chat.
If You Could Master Any Hobby Instantly, What Would It Be?
We all have hobbies we’d love to try but haven’t had the chance (or patience) to learn yet, so with this, you can let them indulge in a bit of imagination. And what they choose to respond with shows what they find exciting or calming, giving you a sense of the activities that would enrich their life.
What’s a Place That Feels Like Home to You?
Home isn’t always where you live—it’s where you feel a deep sense of belonging—therefore this prompt invites someone to reflect on their emotional connection to a place, such as a favourite holiday destination that they never stopped thinking about. It’s always good to know the place that someone would call home and why.
What’s the Most Spontaneous Thing You’ve Ever Done?
A great way to uncover their playful or bold side while encouraging them to relive a fun moment they’re happy to share—ask them this, because spontaneity often leads to the best stories. Whether they once booked a last-minute trip, took a chance on a new job, or jumped into a lake on a whim, you’ll want to know.
What Song or Band Do You Always Recommend to People?
Music has a way of creating instant connections, and asking about someone’s favorite recommendations often sparks a passionate conversation about a timeless classic they’ve loved for years. You’ll see through the window into the sounds that make them happy and have some great additions to your own playlists.