skip the small talk: a conversation with Kate Terentieva, creator of Off the Record

How a card game can help you ask better questions and spark real connection

As part of Love, Writing, where I explore the craft and heart of storytelling, I’m chatting with writers and creators whose work I admire. These exclusive Q&As for paid members are a chance to dive into their creative worlds, hear about their journeys, and share a little of the magic behind the scenes. I hope these conversations spark something in you too.

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Happy Easter, friends (to all those who celebrate)! Whether you're spending the day with family, friends, or just trying to dodge awkward convos with relatives you haven’t seen in a minute—this one’s for you. I got to chat with Kate Terentieva, the creator of Off the Record, a card game designed to turn small talk into deep talk. Which is perfect, because if you're anything like me, small talk is definitely not my fave!

Kate is a creative director and self-proclaimed chatterbox who’s passionate about meaningful conversation. Growing up, she was the girl who could talk to anyone, but as she got older, she noticed conversations often stayed surface-level. During the pandemic and struggling with her own loneliness, Kate realized how disconnected we’ve become and created Off The Record as a way to foster deeper, more authentic conversations. For her, it’s all about building connections that leave you feeling seen and heard, and helping others break free from superficial chats with fun, intentional prompts.

The pocket-sized conversation game is designed to spark meaningful dialogue and deepen connections, and comes with 45 cards with 90 questions and an easy-to-follow booklet to guide you on your first game.

I'm all about connection, I'm all about games, and Off the Record kind of has it all. It's a tool for getting closer—to your friends, your family, or your partner. Or maybe even that cousin you haven’t seen since 2019.

I’m interested in trying out this game with the new guy I’m seeing! I really like asking deep questions, but sometimes I don’t know what to ask! Plus we both like games, so this is a refreshing way to get to know each other better while also having some fun. :)

I asked Kate why she created this game, how to actually use the cards without it feeling awkward, and why it’s totally normal to be a little scared of asking real questions—but also why those deep, deeeeep questions are actually everything when it comes to creating authentic connection with those we love (or at least like a little). Let’s get into it.

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What inspired you to create Off the Record? Was there a specific moment that sparked the idea?

Oh my goodness, I’ve always loved a good conversation. Growing up, I was a social butterfly, a chatterbox, the girl who could talk to a wall. Making friends was easy breezy!

As I got older, I started to feel a shift. Conversations were rarely going beyond work or surface-level celebrity gossip. I noticed the other person was also itching to talk about something more interesting, but was either too nervous or didn't know how to make the transition.

I began to wonder...despite spending a lot of time around people, how well do we actually know each other?

Then COVID-19 brought in-person interactions to a total standstill, giving me the perfect opportunity to solve the pandemic of superficial conversations, especially since my professional background is in communications.

I thought, “How can we improve our overall happiness by feeling more connected to the people in our lives?”

This led to me to create Off The Record. I developed the game to help my friends and me build strong conversational habits by asking better questions, fueling more enjoyable, unforgettable interactions. Now, Off The Record is in hundreds of pockets, handbags, and homes around the world! We’re even loved by Jay Shetty & Radhi Devlukia, Whitney Eve Port, Dear Media, Cosmopolitan, Girlboss, and SXSW :)

it’s time to get deep with your peeps!

How did you choose the prompts for the deck? What makes a great question for deeper connection?

All 90 questions in the deck were pulled from a list of 400+, all of which I would ask my clients – I have a creative direction background in the advertising industry, one in which it’s impossible to find success without investing in relationship-building.

Since most of my clientele were founder-led brands or ones with lean startup teams, I approached my work with this philosophy: “If I understand the people behind the brand, I can better connect their story to their target customer.” When I saw how cathartic these conversations were for my clients and how deeper our relationships grew with one another (many of them are friends of mine to this day!), I realized these questions were meant for an even bigger purpose. The rest is history…

One of my personal favorite questions (and a great alternative to “soo…wHaT dO yOu Do?”) is “Introduce yourself as your superpower.” It’s such a great way to shift our identities from our jobs and think about what makes us special as human beings!

Why do you think people tend to stick to surface-level conversations, especially in dating and relationships?

From my experience, I’ve found it’s a mixed bag of the following:

• Fear of rejection

• Not enough shared values or interests (we don’t need to be the same, but building some common-ground is important for connection)

• Feeling as though you don’t have anything interesting to say

• Fear of someone using what you share against you

• Social anxiety, or the fear of judgement or negative perception

• Thinking that the other person won’t hold space for what you share

• Pressure to conform to social norms

• Being taught that asking questions makes you a burden and you should just “mind your business”

• Needing more time to express your thoughts intentionally and feeling as though you may not be given that grace in a conversation

• Fear of conflict or disagreement

• Not wanting to accept the reality that deeper conversations force them to face

Then, of course, there are people that simply don’t enjoy emotionally or intellectually stimulating conversations, but I don’t 100% believe that – I think maybe they just haven’t been asked the right questions because, at our core, most humans crave (and evolutionarily desire) emotional connections with others through conversation.

Sometimes I hesitate to ask deeper questions—not because I’m afraid to open up, but because I worry I won’t know how to hold space for the response. What advice do you have for that?

That’s okay! Remember, you’re not there to fix that person. You’re just there to serve as, quoting Gabor Maté here, “as an empathic witness.” That’s where active listening comes in, ensuring the person feels heard and seen, even if I won’t always understand. Depending on the question posed, I sometimes like to follow-up with, “Would you like my thoughts or do you prefer I just listen?” or a simple “Tell me more about…” can help them see that you’re trying to understand how this lived experience shaped the person sitting in front of you today.

For someone who isn’t used to asking more intentional questions, where’s a good place to start?