6 unusual questions to spark engaging conversations

Ever find yourself stuck in a conversation that feels about as exciting as watching paint dry? 

We’ve all been there. The awks chit chat, the mechanical smiles and nods, and of course, the dreaded glances at the time on your home screen.

But what if there was a secret to changing all of that?

It’s not about becoming the most captivating person in the room. It’s not about being the life of the party. It’s not even about having a repertoire of dazzling stories. 

It’s a simple yet profound principle: if you want to be interesting, be interested. 

Now, this quote is often attributed to a number of people, anyone ranging from self-help authors from the 1980s to actor Jane Fonda, but the origins aren’t super important. It’s more about where it takes you!

Keeping the focus on being interested, rather than interesting, can help you to dive into the fascinating world of genuine curiosity, active listening, and the unexpected power of putting others in the spotlight. 

If you’re ready to flip the script on dull small talk and become the magnetic force that draws people right in, let’s take a look at some quirky, game-changing questions you might like to whip out when you next need them.

We’re also going to be suggesting some fun follow-up questions so that you can really keep the ball rolling!

Let’s start with one question that’s all about our hidden friends of the forest: mushrooms.

1) “If mushrooms had personalities, which type of mushroom do you think would be your best friend, and why?”

Portobello. Enoki. Chestnut. Everybody’s got a favorite kind of mushroom. (Either that, or they can’t stand them at all!)

If you ever find yourself yearning for that perfect conversation starter to break the ice—which is probably why you’ve arrived at this fair article—don’t be afraid to turn to your favorite funghi.

Try this one on for size: “If mushrooms had personalities, which type of mushroom do you think would be your best friend, and why?”

This one’s a great one because mushrooms are undoubtedly enchanting, quirky, and downright whimsical wonders of nature.

They’re not just a matter of pizza toppings—mushrooms can be a hidden trove of intriguing stories, symbiotic relationships, and an array of mind-bending varieties. 

So, why not sprinkle some fungal fascination into your next conversation? 

On that note you might even like to have some mushroom facts up your sleeve, like the Mycena chlorophos, which is known as the “glowing mushroom.” 

These are the species of mushrooms that have bioluminescence, meaning they can produce light. 

These mushrooms emit a soft, greenish light that is believed to be a result of a chemical reaction involving luciferin and luciferase, similar to the light-producing mechanisms in fireflies.

How great is that?!

Bonus follow-up question: “If you were limited to eating mushrooms in one specific cuisine or dish forever, what would it be, and what makes that particular preparation so irresistible to you?”

2) “If your life had a soundtrack, and you could only listen to one genre of music for the rest of your life, what genre would it be, and how do you think it would influence your daily experiences?”

Okay, so if you want to avoid forever being labeled as “that weird mushroom guy”, you might like to roll out a few more questions, like…

“If your life had a soundtrack, and you could only listen to one genre of music for the rest of your life, what genre would it be, and how do you think it would influence your daily experiences?”

Let’s explore why this question is set to get tongues wagging.

Whether you find comfort in the intricate harmonies of classical music, get your adrenaline pumping with the beats of house music, or seek poetry in the lyrics of folk songs, your chosen genre becomes a mirror reflecting your emotions, aspirations, and how you navigate life.

Consider the emotional landscape that different genres cross, there are the soulful blues that capture the essence of melancholy, the rebellious spirit embodied in punk rock, or the infectious joy emanating from flamenco.

Each genre is a gateway to a distinct emotional world, influencing not just our moments of celebration but also offering a peaceful embrace during times of solitude.

The influence of a person’s chosen genre goes beyond mere musical preference, it becomes the lens through which they perceive and engage with the world.

Moreover, the “life’s soundtrack” question serves as a charming conversation starter because it invites storytelling.

People aren’t just sharing the innermost workings of their Spotify playlist, they are unraveling the narrative of their lives through the precious medium of music.

Anecdotes about the first concert attended, the song that got them through tough times, or the track that they fell in love to, these stories create a portrait of shared experiences and personal histories.

Bonus follow-up question: “What’s the most oddly-specific Spotify playlist you’ve ever come across?”

3) “If you could create a new emotion that doesn’t currently exist, what would it be called, and how would you describe the feeling it represents?”

Now here’s one for the deep thinkers.

(Because of this, I wouldn’t recommend throwing this one out into the arena right away—it’s certainly one to work your way up to!)

Next time the chat gets a bit stale, try this one on for size: “If you could create a new emotion that doesn’t currently exist, what would it be called, and how would you describe the feeling it represents?”

Now, why is this such a powerhouse conversation starter with strangers (aka friends you haven’t met yet!)? 

Well, it’s because it taps into our shared human experience while allowing for a deeply personal response. 

Suddenly, the conversation shifts from the usual script and people—strangers, really— start envisioning emotions that might encapsulate moments they’ve never had words for in the past.

It triggers us to reflect on our emotions, bringing an element of introspection that’s rare in everyday chit chat.

The question isn’t just an icebreaker, it’s a catalyst for connection, sparking discussions that wander well into the world of imagination and self-discovery.

Bonus follow-up question: “If you had to cast actors to play your emotions, who would you choose?”

4) “What’s the weirdest food combination you enjoy that others might find strange?”

French fries dipped in ice cream. The savory combination of peanut butter and bacon. Strawberries and balsamic vinegar.

Who doesn’t love to indulge in the surprisingly delightful world of unlikely, uber-specific food combinations?

We’ve all had the classics—the sweet and savory duos that comfort our senses. But here’s to the daring outliers that tantalize our palates.

These aren’t just food combinations, they’re flavorful experiments that challenge norms and redefine our expectations of taste..

So, here’s the question that turns boring conversations into memorable feasts: “What’s the weirdest food combination you enjoy that others might find strange?”

This is more than just satisfying taste buds, it’s about diving headfirst into the delicious unknown and discovering the nuances that make a person’s foodie preferences distinctly theirs. 

Bonus follow-up question: “What’s the weirdest cocktail you’ve ever had?”

5) “If you were stranded on a deserted island and could only bring three non-essential items, what would they be?”

Picture yourself marooned on a sun-drenched island with nothing but the crashing waves and the rustling leaves of palm trees to keep you company.

Now, here’s the kicker: you’re allowed three things to make life a little easier.

Intrigued? Well then you might like to ask your new friend or acquaintance this: “If you were stranded on a deserted island and could only bring three non-essential items, what would they be?”

This scenario isn’t just about playfully imagining your own version of Survivor, instead, it’s a reflection on our values, a mental exercise that unveils the essence of what we hold nearest and dearest. 

It reveals a great deal about our priorities, our attachment to material possessions, and the delicate equilibrium between necessity and desire.

Bonus follow-up question: “What role would you play on a deserted island?”

6) “If your life had a slogan, what would it be, and why?”

Everybody loves a catchphrase. Building on this, you might like to ask the following question…

“If your life had a slogan, what would it be, and why?”

Beyond the initial curiosity it sparks, this question invites people to bottle the essence of their life and character into a few words, capturing their values, aspirations, and perspectives in a quick yet deep way.

Whittling down the complex make-up of one’s entire life into a single slogan requires a huge amount of clarity and concentration.

Suddenly, the person you ask is confronted with the (hopefully fun) challenge of articulating the driving force behind their choices and the ethics guiding their journey.

These catchphrases become windows into each of us, offering a glimpse into the motivations and experiences that shape each individual.

Bonus follow-up question: “If you had to design your own personal logo, what would it look like?”

Final thoughts

These six quirky questions are great conversation starters because they make people open up in creative and unexpected ways.

They rise above the usual humdrum, encouraging people to share interesting aspects of themselves that might not come up in regular conversations. 

Whether imagining forest mushrooms with personalities or inventing a new emotion, these questions prompt fun and imaginative discussions. 

By exploring the unusual, they help break the ice, create a playful atmosphere, and allow people to connect on a deeper level

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Tina Fey

I'm Tina Fey, the founder of the blog Love Connection. I've extremely passionate about sharing relationship advice. I've studied psychology and have my Masters in marital, family, and relationship counseling. I hope with all my heart to help you improve your relationships, and I hope that even if one thing I write helps you, it means more to me than just about anything else in the world. Check out my blog Love Connection, and if you want to get in touch with me, hit me up on Twitter

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