Adrian Volenik
Small talk is important, but what’s even more important are meaningful conversations.
Engaging in noteworthy discussions involves moving beyond small talk and delving into deeper topics.
It’s not just the questions but genuine interest and active listening that help turn a simple conversation into something meaningful.
And while many phrases can help transition from light and polite conversation to more significant discussions, these are my favorite ones.
1) “What’s something new you’ve tried recently?”
People like trying new things, and what they like even more is talking about what they found, tried, or learned about.
Although most conversations where I use this phrase to open up dialogue end up with talk about new restaurants or foods, sometimes they lead to revelations about personal growth, curiosity, or adventurousness.
You can help steer conversation any way you like or even start by sharing your experience with something new and noteworthy you’ve done or tried yourself.
2) “Have you traveled anywhere recently?”
Another favorite question that I like to ask is, “Have you traveled anywhere recently?” I use it because I’m genuinely interested and love to talk about travel with other people.
Many times, I get ideas for my own travels and even help when I want to decide between two places of interest.
Most people are like that. They love talking about their trips and adventures.
An alternative to this question is, ”What’s a place you’ve always wanted to visit?” This can spark up a great conversation that will tell you a lot about the person you’re talking to.
Also, this next phrase continues in a similar tone.
3) ”Do you have a favorite place in the city?”
This simple question can tell us a lot about a person, and especially about what environments or locations they enjoy and why.
After you get the answer, you can ask many different sub-questions about it. Just try not to overwhelm the person you’re talking to.
You might even find out they like the same places in the town that you like too. That means you already have at least some things in common.
4) ”What’s a goal you’re currently working towards?”
People are motivated by many different things. Some are motivated by money, others by ideals or people.
To quickly find out what push a person has in their life, ask them what goal they’re working towards at the moment.
This will tell you how ambitious they are, if at all. I typically get work-related answers to this question, so I have to dig around a bit to get their personal motivations outside of the office.
5) “Tell me about a book/movie/TV show that has had a profound impact on you”
This easy conversation starter will get the convo juices flowing. Most people love one or all of these entertainment sources, so it’s a good icebreaker to throw at somebody.
I sometimes straight up tell them what my favorite TV show is and then ask them about theirs. Like with travel, it’s a great way to discover new things and connect with people.
Now, let’s switch gears a bit.
6) “What does a perfect day look like for you?”
If you want to keep the conversation going and want to find out what makes someone happy, try using this one.
It will reveal what aspirations and even values someone has. They might opt for a cookie-cutter answer of lying on the beach the whole day. But hey, who doesn’t like that.
At other times, people might share much more details. This includes sharing their favorite foods, places to go, things to do, people they spend their good times with, etc.
All in all, you can’t really go wrong with this one.
7) “What’s something you’ve learned/heard recently that surprised you?”
This one’s similar to the first phrase but has a twist. I got inspired for it by the subreddit r/todayilearned, where people share what they learned that surprised them.
I find it fascinating that with so much information we learn each day, there are still things that can surprise or inspire us.
For instance, a person I recently struck up a conversation with told me about a Japanese astronomer and solar observer, Hisako Koyama. She hand-drew sunspots every day for more than 40 years!
With her meticulously crafted sketches, she provides invaluable assistance to researchers in their study of solar cycles and the intricate magnetic fields of the sun.
It’s gems like these that I love finding out from other people!
8) “What is something you wish more people understood or were aware of?”
When you ask this question, you give the person you’re talking to a chance they don’t often get.
They get to share their perspectives on important topics or issues that they feel are often overlooked or misunderstood by the general population.
It’s usually a topic that’s close to their heart, and they don’t get to talk about it a lot.
9) “Have you had any memorable dreams lately?”
Okay, now we’re talking. If you want to know the good stuff about people, simply ask them this question. It might catch them off guard, but what they tell you might surprise and amuse you.
The two of you might even laugh out loud at the answer they tell you.
But above all, you’re inviting them to share something personal and often deeply symbolic. Dreams can be a window into someone’s subconscious, revealing their hopes, fears, or just the random musings of their brain during sleep.
Let’s see some other powerful questions to spark up a meaningful convo.
10) “What’s one thing you believe in strongly, even if it goes against popular opinion?”
Oh boy, this one’s a doozy. Depending on the person you’re talking to, you might end up with some wild and mind-boggling answers.
If you hear an opinion you strongly disagree with, stay calm and remember you asked for it! Don’t judge people, and try to find out why they believe what they believe.
I love this question as it helps me get away from the bubble of like-minded opinions.
Okay, we have one deep question left, and the rest are lighthearted.
11) “How do you find meaning or purpose in your daily life?”
This question invites people to reflect on the sources of fulfillment and purpose that drive their everyday actions and choices.
By expanding on this question, you can encourage a deeper exploration of how they cultivate meaning and purpose and the ways in which it influences their overall well-being.
You might learn more about their family, pets, friends, community, or work.
12) “What’s your favorite way to spend a weekend?”
If you aren’t aware, there are many so-called “weekend warriors” among us. They love talking about their adventures, hobbies, or interests they get up to on weekends.
Some people might not seem like it, but they could be into some wild stuff like Onewheel off-road racing, extreme ironing, swamp football, dirt polishing, etc.
Who knows, you might just end up joining them the following weekend.
13) “What is something you’re looking forward to in the near future?”
This question is another awesome way to turn small talk into a meaningful conversation. It gives the other person a chance to share their aspirations, plans, or things they are excited about.
On the other side, it helps you understand their priorities and what they value or enjoy.
For many people, the stage where they plan something is more exciting than the thing itself. I certainly count myself here.
By spending days, weeks, or months thinking about the trip, party, concert, event, race, or whatever, I have the chance to think about something else that doesn’t include work, bills, responsibilities, mortgage, etc.
14) “What is something that always brings you joy?”
Joy is a profound and uplifting emotion that brightens our lives and fills our hearts with warmth.
For each individual, there are unique sources of joy that never fail to bring a smile to their face.
It could be an activity, a passion, or even a simple moment of connection. Understanding what brings us joy allows us to cultivate happiness and create more meaningful experiences.
Again, you’ll learn about their family, friends, hobbies or interests, and many other things that bring joy to people’s lives.
Final thoughts
There you have it. 14 ways to turn a casual conversation into a meaningful one. People will open up very quickly if you ask them a fitting question. It’s really that easy.
There’s no reason why we’d need to talk about the weather, last night’s game, or politics for more than a few courteous sentences.
After that, we can steer the conversation in a more noteworthy direction.
