30 Unique Questions to Actually Start a Conversation

One thing about me…? I’m a yapper. Shamelessly. Whether the habit is due to my inability to tolerate sitting in silence, or my incessant desire to ask questions about anything and everything, I can’t say. Regardless, the inarguable fact is that I love to talk. A lot. Thankfully: my time as a Professional Yapper has paid off! I’m here to share a curated collection of my most engaging conversation starters just for you.

Admittedly, as I’ve matured, so have my yapper tendencies. Conversation has evolved from “Who do you think is cutest in math class?” and “If you could have a superpower, what would it be?” to topics that hold substantially more weight.

Instead, I ask them questions the likes of, “How did that conversation with your mom go? Was it as triggering as anticipated?” and “How have you been since you’ve stopped speaking to your last roommate? Did you get your plates back?”

Becoming an adult inevitably shifts the caliber of the conversations we have with those around us, holding substance in a way they couldn’t when we were school children. While the depth of these topics serves to forge deeper, longer-standing relationships… What are we supposed to talk about when we don’t know much about the person across from us? When it comes to sparking new, genuine conversation as an adult, it can be so strange searching for a way to — for lack of a better phrase — “break the ice.”

The good news? It’s not just you.

At this age, when proximity to peers isn’t as consistent as it was when we were teens in high school, and “adulting” is beginning to grow into a behemoth of a monster that we’re all fighting to wrangle, finding the ability to do something like start a conversation can feel taxing where it once felt simple.

While this struggle to make new friends may feel daunting (or even, I can admit for myself, a touch embarrassing at times), Jesayah Hamilton, an experienced Associate Professional Clinical Counselor who works as an Associate Marriage and Family Therapist, assured those of us at Trill Magazine that it’s not as rare for young adults to struggle to build new friendships as one may think.

A full-time therapist who finds herself fascinated by the growing gap in young adults’ abilities to have unfamiliar conversations with one another, Hamilton spoke with Trill regarding the difficulty that seeking to forge connections with others can entail.  Speaking candidly of her own experiences within her career, Hamilton shared, “Finding and creating new and genuine bonds with peers is a topic that comes up a lot with my clients.” That said, what we don’t talk about often enough is society’s role in this newfound difficulty adults [18 – 30 years old] have making new friends.

“Consider society’s emphasis on ‘hustle culture,” Hamilton elaborated.

Could she be more spot-on…? In the age of social media, in which everything is incentivized, scrutinized, compared and demanded, how are we supposed to find value beyond what money we make? What “toys” we own? How are we, as young adults, supposed to find a way to surround ourselves with connection when society grows increasingly more focused on the solitary individual?

What does this mean for us?

Hamilton sparks an interesting question when sharing her observations: Where do we go from here? What does this struggle for connection mean for Gen-Z as a generation? We’re 20-somethings (or about to be) fighting to make friends beyond our social media mutuals. If we’re all struggling to fight through society’s attachment to “hustle culture,” how do we find connection with one another despite its isolating emphasis on individualism?

Hamilton elaborated, “[Taking into account society’s role] isn’t to also say the problem — and therefore, solution — doesn’t rest with us in any capacity. We as a community have lost connection with, and understanding of, one another because we aren’t having conversations that go beyond our individualistic head spaces….” This is important to note. Just because we’re in a hard place doesn’t mean changes can’t be made. If we hope to build a true community amongst each other (especially as things worldwide feel more unstable), it’s on us to find one another and begin together, despite our trepidations.

“You ask someone today, ‘What do you want from life?’ and most people answer ‘Stability, a home, a car,’ and all of that is good and important. But what is any of it for, if not connection with others?” Hamilton continued, eloquently framing exactly why it’s so imperative that we bridge this gap amongst one another. All that we work for amounts to very little when it comes without human connection.

Where does this behavior come from?

Where is it, then, that this instinctive self-isolation seems to originate from within young adults? Most children and teenagers are raised in environments surrounded by their peers nearly every day, whether because of classes, extracurriculars, after-school programs, or otherwise. Why do we, as budding adults, struggle to grasp the social habits that were instilled into us from such early ages?

Hamilton reassured Trill that, while responsibility certainly lies upon us as individuals to develop better habits, our elder’s past habits cannot be discounted. They may even help to inform us as we work to trudge into adulthood. “Unfortunately, most people [of an older] age simply haven’t been taught or prepared to understand their emotions and deeper selves. Our parents and caregivers have coped and pushed through their own traumas the best they could, and often with a severe lack of support.”

“Most of us weren’t taught [growing up] that our feelings are important, so how can we be comfortable opening up and giving our emotions to others? It’s uncomfortable, and risky, because you never know what you’re going to get. Deeper conversations lead to deeper emotions that many individuals don’t know how to manage. In this, bravery can be found in being willing to be open to others first, and spark the initial flames of conversation.”

Being the chronic conversationalist that I am, you can imagine the trepidation this sentiment left me with. Still, Hamilton’s encouragement to create conversation despite any fear of rejection emboldened me.

What’s next, then?

We are, as adults, inaptly equipped to function while isolated, and at its core connection begins with conversation. We all deserve to love radically, and hold space for one another with warmth and empathy, even if we struggle to learn how.

Never fear, dear readers (and fret no longer!), for I am here with a solution: A certifiably unique list of questions you can ask the people in your life to create meaningful connections.

Whether you’re trying to impress the person across from you at the bar, start a conversation with someone in a long line, or get to know a friend on a more personal level, I have a conversation starter for you (and — as a special treat for the sake of loosening up those with tighter lips — I’ve included optional instructions that turn this list of queries into a Getting-To-Know-You drinking game. The questions grow more intimate as they go, so following the game along its pre-written path is likely to lead to more open conversation surrounding some of the more intimidating questions later down the line).

Without any further ado, here are 30 Unique Questions to freshen up your ability to spark a conversation:

Questions to ask strangers

Sharing a communal table at a cafe? Standing in a painfully long concert line? Or worse– Stuck in the mosh pit for hours? Maybe you’re sitting in class and your professor is running late. Spark something engaging with those around you:

(If drinking: anyone who cannot or will not elaborate on their answers takes a drink for each withheld detail.)

1. Where does your subconscious reside in your body?

Imagine your subconscious is a small marble. Where, exactly, does that marble sit?

2. What is something you hope people notice about you?

3. What’s one normal thing you’re really bad at, and one obscure thing you’re really good at?

I, personally, have nothing short of a horrific sense of direction. Thankfully, I am also gifted with the ability to properly put a duvet in its comforter without any folds or wrinkles in less than 30 seconds.

4. If you had to separate your life into a “before” and an “after,” what would be your life’s defining moment?

5. If you could know the answer to any one unsolved mystery, what mystery would it be?

Hamilton feels strongly about solving the mystery of Jonbenét Ramsey’s murder… an inarguably adequate answer, and not the first (nor, likely, the last) time I’ve received it.

Questions to ask when you have 30 seconds to make an impression

Out at the bar? Have a blip of a chance to chat with someone who’s caught your eye? Eager to make sure someone remembers you? No sweat.

(If drinking: If either/any of you can’t think of an answer to your question within 30 seconds, take three drinks.)

6. If I had a box containing everything you’ve ever lost, what would you search for first?

7. Besides the line “you only live once” what’s the line that you drop before you make an incredibly bad decision?

I’ve found the popular answer in my household is, “Money comes back!” Though I’m not sure that theory’s been proven, my breath remains bated, and my fingers crossed.

8. How do you visualize time?

9. If you could haunt anyone, who would it be? Why?

10. If you could tell a “new” soul to experience one thing on earth before they disappeared forever, what would you tell them to do?

Questions to ask people you want to know deeper

You know that awful feeling when you’re soaked up in a friend-crush that you’re unsure about? You’ve met a potential friend: they’re cool, and you enjoy their time, but you can’t quite figure out how to know them beyond brief chats and promises of hanging out. Don’t worry, babe, I’ve got you.

(If drinking: Anytime your partner’s answer to a question surprises you, take a drink.)

11. What’s a pivotal moment in which you knew you had to change something in your life, and acted on it?

It’s that “and” that tends to make people pause. Recognizing a need for change is the easy part. Acting upon the knowledge? Brave, and far more difficult in motion than it is in theory. Never forget to ask the “and.” It’s the details that count.

12. What’s something you have an opinion on that you don’t think many other people have any thoughts on?

13. Imagine a room full of everyone you’ve ever met. Who would you look for first?

14. In what ways do you feel most misunderstood as an adult?

15. What’s your favorite smell, and what memory do you associate with it?

Maybe this is corny, but my late father and I always used to go to ARCO gas stations for their hot chocolate (the best hot chocolate you’ll ever find for less than $2, by the way). No matter what state I’m in, every ARCO smells the same. It makes me miss him, and feel briefly closer to him every time.

Questions you should only ask the bold

Occasionally, some of the most enlightening questions can be stale, when the receiver of them is unwilling to answer honestly. Here are some conversation starters that often create fascinating exchanges, so long as whoever answers is bold enough to give any gritty truths they may have.

(If drinking: Claiming to be brave enough to answer these questions raises the stakes! Any question someone is unwilling to answer, they must finish their drink.)

16. Do you have any conspiracy theories that you truly believe in, but others generally don’t? Explain why, and defend your side if anyone disagrees.

17. What’s one random, bitter resentment that you hold against someone? Extra credit if it involves someone in the room with you.

Personally, I never truly forgave the girl who stole my Pink Nintendo DS out of my backpack in our first-grade class. She was my friend and everything. She gave it back, and we’re cool now, or whatever, but still…

18. What’s the last incorrect thing you’ve done?

Sometimes, when I ask this question, near strangers will tell me about a terrible betrayal they’re desperately regretting committing against a close friend. Other times, someone tells me about the name they mispronounced at work that day. I suppose you could call this question something of a “wild card.” It’s one of my favorites for this reason.

19. What is hardest for you to say as an adult: I need help, I’m sorry, or I love you? Why? Give details if there is a specific memory or event associated with your reasoning.

20. What do you hope people will say at your funeral? Further, what do you fear people saying?

Therapist-approved questions

While conversing with Hamilton, she confessed to me that she has an interest in curating a “question’s deck” in her future: a box of questions with a concept similar to that of We’re Not Really Strangers, focusing on questions that can be built upon, encouraging intimate conversation between friends that are often otherwise exclusive to a therapist’s office. She encourages asking these questions in group settings so that each individual member can be pushed to share their own opinions, advice and experiences in a setting with differing experiences.

(If drinking: Anytime someone gives an answer that resonates with you, take a drink.)

21. What’s your best friend’s biggest pet peeve? Explain why to the very best of your ability.

Hamilton feels like this is one of her more effective conversation-initiators. It allows all parties to discuss something neutral, that they find warmth in, while still attuning themselves to the details and intimacies of one another. You can learn much from the way someone describes the people they love.

22. What’s a non-romantic relationship you should have left sooner? What kept you from leaving? Would you change anything looking back on it? If you had changed it, what would those changes have meant for you?

23. With as little information provided as possible, look around the group and describe what role you think each of them played in their household growing up, based on what you know of them as adults.

Hamilton clarified this question further for Trill. While roles such as “golden child,” “scapegoat,” and “forgotten middle child,” are roles well-known in conversation about family dynamics, there are many other, more abstract roles. When answering this question, consider lesser-known options, such as The Enabler, The Rescuer, The Hero, The Mascot, The Lost Child, or anything else you may come up with. Try to think beyond the “norms” of family dynamics.

24. What reality show do you think you would do best on? Why?

Hamilton admitted, as she shared this query, that while she understands that the question may sound a bit frivolous, in truth an answer to this question says quite a bit about the adult it belongs to. It can speak to their confidence, their insecurities, their strengths, and weaknesses. Someone who feels they’d conquer Survivor is certainly different from someone who may appreciate the initial privacy of the pods offered in Love is Blind. Plus, considering different shows and roles within them can be conversation starters of their own accord.

25. If you were to die tomorrow, how would you want your belongings distributed?

This question, in particular, struck something within me. As a queer individual who values chosen family as deeply her blood, this made me wonder how typical queer responses may vary in comparison to the typical cis-gendered, heterosexual answers. Food for thought.

Questions to ask those you already know

Have a best friend you think you know everything about and working to strengthen that relationship even further? Someone you’ve asked every question under the sun? That one person who you can never seem to take off guard? I bet you haven’t asked them anything like these questions:

(If drinking: Try to guess your friend’s answer. Answering wrong means you a drink. Answer correctly, and they drink instead. If you have the same answer — before discussing it  — finish your drink.)

26. Tell a story about a memorable mixed tape or playlist that was made for you, and still evokes emotion to this day.

27. If you could eliminate one human emotion, which would it be?

In my humble opinion, the answer feels obvious: anxiety. Without hesitation. I’d do anything to rid myself of it. Fear, or hesitancy, can be healthy at times, but anxiety…? That unrelenting, senseless feeling of fight or flight? I can’t imagine why anyone would choose to eliminate any other emotions. And yet, I am given many different answers by others: anger, embarrassment, self-doubt. I find this to be one of the beautiful aspects of using conversation starters like these with adults. Every one of us has experienced unique childhoods and early adulthoods, and our different relationships with our emotions can shape that experience more than most realize. If I live my life avoiding my anxiety, I very likely live life differently from someone who may spend their time doing whatever they can to avoid the feeling of lacking control.

28. If your pet had pockets, what would they carry?

An obscure, and maybe ridiculous query, I know. But have you ever really thought about it? My blind cat would carry a pawful of loose puzzle pieces, and her sister would definitely be well-stocked on loose anxiety medication. Anyone I ask this question to tends to have long-winded, and detailed answers to give, and it’s always enjoyable.

29. If you were a robot, and didn’t know, but I knew, would you want me to tell you?

I have yet to decide my own answer on this. Ignorance is bliss…. But would knowing I was a robot give me special abilities as a piece of technology? Would I benefit from knowing more than I would ache? My partner says she wouldn’t want to know, so long as my memory was wiped and I didn’t know, either. Her answer, admittedly, is much better than my lack of one by default.

30. When was the last time you did something for the first time?

Extra credit: For those willing to go the extra mile

If you’ve made it this far, give yourself a pat on the back. I’m proud of you. It takes courage to take steps toward being vulnerable, and I recognize that. In fact, just for you, here are three bonus conversation starters, if you don’t mind a couple extra steps, and care to go a step further.

31. This suggestion is best for a group: Choose any date at random, and everyone in the room has to pull out their phone to show a picture from that day in their camera roll.

If someone didn’t take a photo that day, they then show a photo from the soonest day after the chosen date. Don’t be afraid to use these photos as conversation starters! (If drinking: Anyone unwilling to show their photo takes a shot.)

32. Instead of just asking and answering the questions, try asking these questions in a group setting. Have everyone anonymously write their answers down on a piece of paper, and then mix the answers in a bowl. Draw the answers at random, and see if the room can guess who wrote the answer!

33. Have someone you talk to often? A roommate, partner, or nightly FaceTime bestie? A simple, valuable, and endlessly recyclable question to ask (rather than an overused “How was your day?”) is “What were you thinking about today?”

In all honesty, I love this question. It’s gentle, yet so effective. It allows you to get to know something small and intimate about the person you’re speaking to that you likely wouldn’t have come across, otherwise. It feels like exploring the nooks and crannies of a loved one’s brain in a whole different way.

Yes. Yes, yes, it’s true. Being an adult can be hard, and confusing, and really weird. Nonetheless, existing is always easier to bear, kinder to stumble through, and safer to fall into when you have community and connection pervading throughout your life.

If nothing else, my dear future yapper, I urge you: Don’t let your fear of rejection stop you from reaching out to those around you. Your bravery in making the “first move” not only acts as a gift to your recipients but as a way to build community in a world that can feel increasingly lonely. Put in the effort to build friendships as an adult that nourishes you. Hold space for others. Listen intently. Inquire fearlessly. You will grow from every question you’re willing to ask, and the world is forever in need of someone willing to hear.