Let’s be honest, we’ve all had conversations with friends that seem repetitive or dull. There are only so many times you can chat about the latest relationship drama, a TikTok pasta recipe you want to try, or the newest episode of The Pitt. Even I, a notorious yapper, find myself getting caught up in talks like this; while it’s not a bad thing to have a silly yap with your friends, sometimes it gets to a point where it feels like you only know how to talk about things like social media or gossip.
As part of my 2026 goals, I vowed to myself that I would try and get smarter. Not just in the traditional book-smart sense, but in ways that make me more well-rounded as a person. In doing so, I’ve been making more of an effort to have deep and meaningful conversations with friends that I otherwise wouldn’t; not because I felt like I couldn’t be serious with that person, but because it was just easier to be silly. However, in testing some of these conversation starters, I found that I was wrong — it is just as easy to carry an introspective conversation than it is to joke around or endlessly quote your favourite TikTok brainrot meme.
So, next time you’re grabbing coffee or on a long car ride with a companion, whip out some of these questions and prepare to be amazed at how well the yapping begins to flow!
“If you were written by any singer, who would it be?”
This is one of my favourite get-to-know-you questions. Since music is one of the main things that binds us as a human species, there’s always one artist that a person claims to be written by. It’s hard not to feel as though their songs were written by crawling into your brain.
Not only does this question apply to the large majority of people, it’s an easy way to gauge how your conversation partner not only sees themselves, but gives them an avenue to talk about their own interests.
“what do you want to be remembered for?”
Not to be dark, but I ask this question to a lot of people. Not even in a doomsday sort of way, but just to see where my friends stand on what they think makes them stand out, or even what values they think will shine through after their exit off of this mortal plane.
Yikes, that was a little dark. Maybe save this one for the buddies you’re already close with, not somebody you just met.
“Do you believe in luck?”
Facets of life such as fate, intuition and luck are so fascinating. There are so many diehard believers, so many who refute their existence entirely, and some who don’t even know where they stand.
This question is a fun one, because it can prompt funny stories of how luck came into play in their lives (or how it didn’t). It’s such a simple way to gain insight on what kind of person you’re talking to.
“If you could instantly learn one skill, what would it be?”
The magic and whimsy that follows asking this question is truly beautiful to see. By inviting someone to imagine what their life would look like without time or financial restraints, it allows them (and you!) to get excited about what could be.
Giving your conversation partner an outlet to voice what they’re passionate about and why they want to be better at it can give you the perfect avenue for bonding over similar interests, or leave room for a deeper level of conversation about why that particular skill means so much to them.
“what is the biggest risk you’ve ever taken?”
Story-based questions are my absolute favourite. Sure, it’s a fun way to laugh or sympathise with who you’re talking to, but it also gives them the opportunity to share something potentially vulnerable about themselves that clearly means a lot to them.
It also leaves room for emotional engagement. Clearly, the anecdote had some sort of stakes in this person’s life (either good or bad), and it gives both people something to react to and build on with follow-up questions like “Why did that risk come about?” or “What happened next?”, no matter the story’s tone.
concluding thoughts
Asking thought-provoking questions like this can not only deepen your knowledge and relationship with the person you ask them to, but it could also allow you to learn new things about yourself! There have been many instances of me asking my friends similar questions, hearing their responses, and gaining a whole new perspective on the subject.
Side note: These questions also work great during games of truth or dare, if you’re stumped on what to ask someone who you thought would choose ‘dare’.