Breaking the Ice: Starting & Improving Conversations for Better Relationships

Turn strangers into friends & make more meaningful connections with your existing friends.
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Breaking the Ice: Starting & Improving Conversations for Better Relationships

November 26, 2024

I’m at Boulderhouse, a local climbing gym in Victoria when I overhear a group of people talking. 

I’ve met a large chunk of my community through climbing. It’s easy to talk to people. If you decide to say hi to a stranger, an instant bond is created. Both of you are working together to solve a problem. 

That’s great and all, but this group was falling into the trap of the “Nice to meet you” routine. 

“Where are you from?”

“Are you in school or working?”

“What are you studying?”’

Uhhhh….

Anyone else turn on autopilot when they hear these questions?

We’ve all been there, myself included! It makes sense to ask the “Nice to meet you” questions but everyone does. 

I’ve noticed that when someone asks me something even remotely different I’m instantly more engaged, excited and happier to chat.

Putting the extra effort into small interactions is something that’s made me feel more connected to people in my community - even if it’s a short conversation. 

We’ve created a list of 10 ways to shift the result of everyday questions so you can feel more connected, engaged and heard while socializing.

Getting to Know Someone After Meeting Them

  1. Where are you from? Vs. How long have you been in Victoria? 

“Where are you from” can be a good question to get into someone’s background, but if you want to get them talking about what they’re up to now, then ‘How long have you been in Victoria” is a great question. It typically results in one of two answers; “born and raised” or “I moved here for work/school/wanted to experience a new city”. Either way, it gives you some more ammunition for your next question, such as “what are you loving the most about Victoria so far?”

  1. What do you do for work/study? vs. What’s been getting you excited lately?

A common route of conversation will revolve around larger parts of people's lives, AKA working or studying in school. These aren’t exciting topics to talk about. Instead a better question is “What’s been getting you excited lately?” This isn’t a question people get very often, but it’s awesome for making them think about their answer and talking about something that, usually, they’re genuinely passionate about. The answer you receive reveals what someone loves - maybe it’s their house plants, their parents are visiting them, they started a new craft project. Let this lead the dance in your conversation and do your best to ask them questions about it. 

  1. What are you doing later vs. What are you looking forward to the rest of the day?

“What are you doing later?” “Probably just chilling, getting some work done”, “Nice”.And there you are. We’re right back to where we started in the conversation, and it’s pretty tough to keep it engaging after that.“What are you looking forward to the rest of the day/week?” is a subtle, yet positive spin on the question. Good times are ahead, even if it’s as simple as getting done with the work week. And, like the question “what’s been getting you excited lately”, it gets people thinking about a positive aspect of their life.Sometimes people have bad weeks,and they might struggle to give you an engaging response. In this scenario, praise them for showing up and just being there - because that in itself is a win.

  1. Have you traveled much? Vs. What’s your next adventure?

Travel isn’t accessible for everyone. While still keeping a sense of exploration try “What’s your next adventure?” “Adventure” looks different from person to person and this question accommodates the ones happy to leave their house, the weekend warriors, and ultimate backpackers.  

  1. What are you doing on your days off? Vs. What’s your favorite way to spend the weekend?

Being more specific is always a great way to spark deeper conversations, even off the bat right after meeting someone!Even just slightly shifting language when asking the basic questions opens up doors for authentic and genuine interactions that will leave a lasting impression on the person you’re chatting with.Try some of these out and do your best to respond to the “Nice to meet you” questions with a new perspective.

More Engaging Conversations

  1. How was your trip? Vs. What was an exciting or ‘oh crap’ moment from your trip?

This is a more specific question, one you might lead them into with a quick “have you done any traveling to somewhere cool within the last year?”. Then you can use this question to get a really unique response that’s different from the usual “Yeah, it was really good” type of travel recap. Rarely does a trip go 100% as planned, so the answer will usually be a fun story that’s engaging for both of you and provide something for you to keep building the conversation off. Plus, who doesn’t love talking about their travels? 

  1. How was your day? Vs. What was your highlight today? 

This question is perfect for service type jobs. Heading through checkout at the grocery store? Ordering at a restaurant? This should be your go-to question.Due to its specificity, the person is forced to sift through their day and pick something that stood out that was positive. There’s nothing better than landing this question on someone that’s having an awesome day. If they’re not, similar to #3, you can always praise them for something they’re already doing.“What was your highlight today?”, “Oh I don’t know, today’s been kind of bad” “Ah well, I’m sorry. At least you’ve made it out of the house today!” Believe me, sometimes this is hard.

  1. How are you doing? Vs. How are you feeling? 

Suited for someone that you’ve met multiple times, swapping out “doing” for “feeling” shows a sense of empathy, listening and care that is oftentimes missed in interactions with this type of friend. Be ready to listen intently and curiously!

  1. What year are you in? Vs. Are you in any clubs or groups away from school?

I’m just now getting out of post-secondary, but if you’re in school or been in school this ones come up more than a hundred times. While still centered around school, ask about the hobbies, groups or clubs that someone might participate in.Sometimes this doesn’t land, and that's okay! Not everyone has the ability to do extracurricular activities. If that’s the case… “What’s something interesting you’ve learned recently?”

  1. What kind of music have you been listening to? Vs. Which artist or song do you have on repeat lately? 

As you navigate your interaction with someone, your main goal should be finding common ground - and who doesn’t listen to music?If this person answers with an artist you have no idea about, even better. Dive deeper and save it on your phone, listen to it later and think of that person every time you hear the song. If you don’t like it, think of it as expanding your ear-palette. If you do, first, you found an awesome new song, and second, the next time you see that person, tell them and they’ll remember you forever.

Breaking the Ice: Starting & Improving Conversations for Better Relationships

Turn strangers into friends & make more meaningful connections with your existing friends.
November 26, 2024

I’m at Boulderhouse, a local climbing gym in Victoria when I overhear a group of people talking. 

I’ve met a large chunk of my community through climbing. It’s easy to talk to people. If you decide to say hi to a stranger, an instant bond is created. Both of you are working together to solve a problem. 

That’s great and all, but this group was falling into the trap of the “Nice to meet you” routine. 

“Where are you from?”

“Are you in school or working?”

“What are you studying?”’

Uhhhh….

Anyone else turn on autopilot when they hear these questions?

We’ve all been there, myself included! It makes sense to ask the “Nice to meet you” questions but everyone does. 

I’ve noticed that when someone asks me something even remotely different I’m instantly more engaged, excited and happier to chat.

Putting the extra effort into small interactions is something that’s made me feel more connected to people in my community - even if it’s a short conversation. 

We’ve created a list of 10 ways to shift the result of everyday questions so you can feel more connected, engaged and heard while socializing.

Getting to Know Someone After Meeting Them

  1. Where are you from? Vs. How long have you been in Victoria? 

“Where are you from” can be a good question to get into someone’s background, but if you want to get them talking about what they’re up to now, then ‘How long have you been in Victoria” is a great question. It typically results in one of two answers; “born and raised” or “I moved here for work/school/wanted to experience a new city”. Either way, it gives you some more ammunition for your next question, such as “what are you loving the most about Victoria so far?”

  1. What do you do for work/study? vs. What’s been getting you excited lately?

A common route of conversation will revolve around larger parts of people's lives, AKA working or studying in school. These aren’t exciting topics to talk about. Instead a better question is “What’s been getting you excited lately?” This isn’t a question people get very often, but it’s awesome for making them think about their answer and talking about something that, usually, they’re genuinely passionate about. The answer you receive reveals what someone loves - maybe it’s their house plants, their parents are visiting them, they started a new craft project. Let this lead the dance in your conversation and do your best to ask them questions about it. 

  1. What are you doing later vs. What are you looking forward to the rest of the day?

“What are you doing later?” “Probably just chilling, getting some work done”, “Nice”.And there you are. We’re right back to where we started in the conversation, and it’s pretty tough to keep it engaging after that.“What are you looking forward to the rest of the day/week?” is a subtle, yet positive spin on the question. Good times are ahead, even if it’s as simple as getting done with the work week. And, like the question “what’s been getting you excited lately”, it gets people thinking about a positive aspect of their life.Sometimes people have bad weeks,and they might struggle to give you an engaging response. In this scenario, praise them for showing up and just being there - because that in itself is a win.

  1. Have you traveled much? Vs. What’s your next adventure?

Travel isn’t accessible for everyone. While still keeping a sense of exploration try “What’s your next adventure?” “Adventure” looks different from person to person and this question accommodates the ones happy to leave their house, the weekend warriors, and ultimate backpackers.  

  1. What are you doing on your days off? Vs. What’s your favorite way to spend the weekend?

Being more specific is always a great way to spark deeper conversations, even off the bat right after meeting someone!Even just slightly shifting language when asking the basic questions opens up doors for authentic and genuine interactions that will leave a lasting impression on the person you’re chatting with.Try some of these out and do your best to respond to the “Nice to meet you” questions with a new perspective.

More Engaging Conversations

  1. How was your trip? Vs. What was an exciting or ‘oh crap’ moment from your trip?

This is a more specific question, one you might lead them into with a quick “have you done any traveling to somewhere cool within the last year?”. Then you can use this question to get a really unique response that’s different from the usual “Yeah, it was really good” type of travel recap. Rarely does a trip go 100% as planned, so the answer will usually be a fun story that’s engaging for both of you and provide something for you to keep building the conversation off. Plus, who doesn’t love talking about their travels? 

  1. How was your day? Vs. What was your highlight today? 

This question is perfect for service type jobs. Heading through checkout at the grocery store? Ordering at a restaurant? This should be your go-to question.Due to its specificity, the person is forced to sift through their day and pick something that stood out that was positive. There’s nothing better than landing this question on someone that’s having an awesome day. If they’re not, similar to #3, you can always praise them for something they’re already doing.“What was your highlight today?”, “Oh I don’t know, today’s been kind of bad” “Ah well, I’m sorry. At least you’ve made it out of the house today!” Believe me, sometimes this is hard.

  1. How are you doing? Vs. How are you feeling? 

Suited for someone that you’ve met multiple times, swapping out “doing” for “feeling” shows a sense of empathy, listening and care that is oftentimes missed in interactions with this type of friend. Be ready to listen intently and curiously!

  1. What year are you in? Vs. Are you in any clubs or groups away from school?

I’m just now getting out of post-secondary, but if you’re in school or been in school this ones come up more than a hundred times. While still centered around school, ask about the hobbies, groups or clubs that someone might participate in.Sometimes this doesn’t land, and that's okay! Not everyone has the ability to do extracurricular activities. If that’s the case… “What’s something interesting you’ve learned recently?”

  1. What kind of music have you been listening to? Vs. Which artist or song do you have on repeat lately? 

As you navigate your interaction with someone, your main goal should be finding common ground - and who doesn’t listen to music?If this person answers with an artist you have no idea about, even better. Dive deeper and save it on your phone, listen to it later and think of that person every time you hear the song. If you don’t like it, think of it as expanding your ear-palette. If you do, first, you found an awesome new song, and second, the next time you see that person, tell them and they’ll remember you forever.

Engaging with strangers and old friends can be difficult and awkward, but the biggest take away from these questions is that you continue to be curious and stay consistent. For example, next time you’re at the grocery store, ask the cashier what their highlight has been that day. Sit beside someone new and class and do the same. Conversation and meeting new people is like a muscle you keep building, the more you do it, the better you get.

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