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Meeting new people can be fun and exciting, but at the same time stressful. It’s a good idea to strive to not only make a great first impression but also find topics that allow you to truly connect on a deeper level. The right icebreaker questions can work wonders for sparking an engaging conversation and developing a solid rapport with newfound friends.

At TOconnect, our mission is to facilitate authentic connections between like-minded people in Toronto by letting you connect with other members online and set up in person meetups. To help you break the ice and get conversations flowing organically, here are 10 fun questions to ask new friends:

1. If you could pick up a new skill effortlessly, what would it be?

This imaginative question allows you to playfully tap into each other's wildest dreams and curiosities. Maybe they'd love to suddenly become a master chef, a fluent polyglot, or have magical coding abilities. It sparks creativity while hinting at ambitions. You’ll probably have at least a couple of common interests. And you never know: maybe you’ll decide to sign up for a class to pick up a new skill together!

2. What series would you recommend me to binge-watch?

Our entertainment preferences can offer insights into our personalities. Discussing the shows we enjoy watching is a great way to find common interests and bond over shared discoveries. Swapping recommendations allows us to venture outside our usual comfort zones and experience new genres. It's also simply fun to debate acting styles, critique plot twists, or laugh about bad shows we secretly love watching. Opening up about the series that transport us to different worlds is a low-pressure way to start to understand each other's unique tastes. You might even decide to binge watch something together.

3. Where did you go on your last great adventure? 

Whether recounting an epic summer road trip or a memorable staycation in the city, travel tales make for superb bonding material. You'll learn about each other's style, openness to new experiences, and the types of trips you each consider "adventurous." It could also be a fun way to plan potential future trips together.

4. If you had to choose one meal to eat every single day for the rest of your life, what would you choose?  

On the surface, this question seems trivial, but culinary obsessions have a way of unlocking common ground and similarities. You may be surprised to discover you both share an unconditional love for local mom-and-pop diners, crazy pizza toppings, or addictively tasty ethnic cuisines. Knowing what your new friend loves and hates can make it easier to choose a place if you decide to go grab a bite to eat after your hangout.

5. What's your go-to music playlist when you’re feeling down?

Music preferences say a lot about someone's personality. The artists and genres we connect with most often align with our energy levels, moods, and mindsets. You may find yourself bonding over similar music tastes or possibly discovering some new artists. Remember to not judge each other’s music tastes and instead try to give all music genres a chance.

6. If you had to describe yourself using only three words, what would they be?

Word association games are always a great way to see each other’s creative side. With just three words, you can gain interesting insights into how a new friend perceives themselves. Their choices might highlight core values, attractive personality traits, or maybe even how they think they appear to others..  

7. What's the most unusual collection you’ve ever had?

We all have at least one weird side hobby, obsession, or maybe even a prized collection. This question will give you both an opportunity to open up to each other and be a bit vulnerable while still keeping the conversation topic comfortable for both. It’s a great way to learn about each other’s unusual passions and to talk about unique topics.

8. What's one secret talent you have that might surprise people?

Part humble-brag, part talent show; this question is all about prompting impressive (and often unexpected) displays of skills and party tricks. Perhaps your new friend can flawlessly recreate bird calls, juggle like a pro, or recite the alphabet backward in multiple languages. It adds exciting elements of mystery, showmanship, and humor.

9. How would you spend an entire day of "you" time with no obligations?

 Self-care rituals and personal indulgences tend to unlock A LOT about someone's comfort zones, coping mechanisms, and how they choose to intentionally nurture themselves. You’ll better understand the other person and what really helps them relax and feel comfortable. This is a great way to learn about each other’s boundaries and comfort zones without being too direct about it. 

10. What's something you're really looking forward to this year?

This is an open-ended question that allows new friends to share their excitement about upcoming plans, goals, personal milestones, or life events. You can open up as much or as little as you’d like. This sneak peek into their mindset and priorities adds helpful context about their current stage of life. It also presents opportunities to provide support, accountability, and maybe even plan celebratory activities together when the time comes.

Key Takeaways 

The most important thing is to keep questions positive and focused on hobbies, interests, humor, preferences, and casual anecdotes. Avoid anything too heavy or too deeply personal until you've established a stronger sense of rapport and trust.  

Remember, great conversations flow both ways. For every question you ask, be prepared to answer it yourself by sharing your own stories, perspectives, and perhaps a few quirks of your own! Vulnerability is key to facilitating an easy, authentic connection.

So whether you're looking for awesome new friends to grab weekly dinners with, partners for active outings around the city, or just some low-key company to attend events - put these icebreaker questions to use. They're guaranteed to spark engaging chats that transform new acquaintances into lasting friendships.  

Are you new in Toronto and looking for ways to feel less lonely? Check out some of our other helpful posts!