20 Lighthearted Questions to Get to Know Someone Better
This article is part of the Friends and Friendship Series:
- How well do You know your Friends? Quiz: Deeper Conversations That Spark Authentic and Lasting Bonds Click Here
- The “How Compatible Are You?” Quiz: Click Here
- How to Transform Casual Encounters into Lifelong Friendships: 20 lighthearted Questions you can ask to get to know a new Friend Click Here
- How to Create a Friendship Manifesto Click Here
- The Most Inspiring Friends and Friendship Quotes Click Here
Introduction
Friendships are like plants—to grow, they need to be nurtured, but they don’t require constant attention. Plants need just the right mix of water, fertiliser, and sunlight to thrive, too much of any of these and they die. The one question I am asked at nearly every Camino de Santiago walking retreat, and certainly at EVERY From Trouble to Triumphant: Find Solida Ground During A Life Quake retreat, is how to make friends and maintain friendships. Friendships become especially valuable during lifequakes, when you need all the help you can get.
This is what I tell my guests:
How to Make Friends
- Get Out There (Even If It’s Awkward):
You won’t make new friends by staying glued to your couch, no matter how tempting Netflix and fuzzy socks may be. Try joining a book club, a pottery class, or volunteering for a cause you care about. Shared interests are a great starting point because they give you a built-in conversation starter. And yes, the first few interactions might feel a little awkward, but that’s normal! Everyone feels like a fish out of water at first. - Be Brave and Start the Conversation:
If you see someone who seems interesting, don’t overthink it. Compliment their shoes, ask what they’re reading, or comment on the event you’re both attending. A simple “Hey, have you been to this class before?” can lead to an hour-long chat about your shared hatred of burpees. - Be Curious (and Genuine):
The key to making friends is showing a genuine interest in the other person. Ask open-ended questions about their hobbies, background, or dreams (see my list below). People love feeling seen, heard and appreciated, and curiosity goes a long way in creating that initial spark. - Be Patient:
Building a lasting friendship takes time. It’s okay if the first meeting doesn’t lead to instant BFF status. Keep showing up, keep reaching out, some connections will naturally lead to life-long rewarding friendships.
How to Maintain Friendships:
Once you’ve found your people, the real work begins—but it doesn’t have to feel like work. Here are some ways to nurture those bonds:
- Stay in Touch (Even When Life Gets Busy):
Friendships fade when they’re left on autopilot. Send a quick “thinking of you” text, tag them in a meme, or drop a voice note. Small gestures show that you value the connection, even if you’re too busy for a long chat. - Prioritise Time Together:
We all have packed schedules, but friendships deserve space on the calendar. Whether it’s a weekly coffee date, a monthly dinner, or a quarterly weekend getaway, carving out time to reconnect is crucial. Even a quick Zoom catch-up works if you’re far apart. - Be Their Cheerleader:
Celebrate their wins and be their support system when life throws them curveballs. Whether it’s a big promotion, a new relationship, or a tough breakup, showing up during those moments strengthens the bond. A simple “I’m so proud of you!” or “How can I help?” can mean the world. - Accept their Imperfections:
No one is perfect, and friends will sometimes mess up or drift away for a bit. Give grace, communicate openly, and be willing to patch things up if the friendship is worth it. - Make It Fun:
Friendships shouldn’t feel like an obligation! Plan activities you both enjoy—movie nights, road trips, or even just binge-watching trashy reality TV together. Shared experiences build memories, and memories deepen bonds.
When Friendships Face Challenges:
Life can be messy, and so can friendships. Maybe your schedules don’t align anymore, or you have a disagreement. It happens! The key is being honest about how you feel. If a friendship truly matters, it’s worth putting in the effort to have a tough conversation. Sometimes, just clearing the air can bring you even closer.
On the other side, if a friendship feels one-sided or toxic, it’s okay to let it fade. Maintaining friendships doesn’t mean clinging to relationships that make you unhappy.
20 Lighthearted Questions to Help You Get to Know a New Friend
- If you could have any superpower for a day, what would it be and why?
- What’s the best advice you’ve ever received?
- If you could only eat one food for the rest of your life, what would it be?
- What’s the most ridiculous fashion trend you’ve ever tried?
- If you were a character in a movie, what genre would it be and who would play you?
- What’s your favourite childhood cartoon or TV show that you still love today?
- If you could travel anywhere in the world right now, where would you go and why?
- What’s the weirdest or most unusual pet you’ve ever wanted to have?
- Do you have any hidden talents or party tricks that would surprise people?
- What’s your favourite way to spend a rainy day?
- If you could only watch one movie for the rest of your life, what would it be?
- What’s the funniest thing that has ever happened to you on a trip or vacation?
- If you could live in any fictional universe (from books, movies, or games), which one would it be?
- What’s your guilty pleasure when it comes to music, TV shows, or snacks?
- Do you prefer cats, dogs, or some other animal entirely? Why?
- What’s the best piece of advice you’ve ever received that made you laugh?
- If you had to choose an animal as your spirit animal, which one would it be and why?
- What’s your favourite board game or card game to play with friends?
- If you could attend any concert (past or present), which artist or band would you choose?
- What’s something on your bucket list that you’re excited to cross off someday?
Feel free to mix and match these questions, they are designed to keep things light and fun while helping you learn more about each other in an enjoyable way.
Why Friendships Matter:
At the end of the day, friends are the people who make life’s highs brighter and its lows more bearable. They’re the ones who’ll cheer you on when you’re doubting yourself, make you laugh when you’re feeling down, and share life’s little joys (like discovering a new ice cream flavour together).
Building and keeping friendships going takes effort, but the rewards are endless. A good friend is like a warm mohair blanket on a freezing cold day—comforting, reliable, and just what you need when life gets rough, especially during life transitions-whether it’s a career change, relationship shift, health challenge, or personal loss. So go ahead: send that text, make that call, join that alternative pottery class or attend a retreat. You might meet your next best friend while you walk part of the Camino de Santiago de Compostela!
I put the essence of who I am, and everything I have experienced that makes me who I am, with great enthusiasm, into my retreats, courses and books. – Dr Margaretha Montagu (MBChB, MRCGP, NLP master pract cert, Transformational Life Coach dip, Counselling cert, Med Hyp Dip and EAGALA cert)
