365 Meaningful Conversations: A space for making connections that run deep

Image by Audrey Phillips

We’ve all heard about the Seattle freeze and some of us have even experienced it. In fact, there is even a cleverly named ice-cream shop called the Seattle freeze.

The term, in general, refers to a social phenomenon about the general unfriendliness of people in the city. It is true—but only on a superficial level. If we dig deeper, people from all walks of life, transplants or not, crave human connection.

The next question is—how do we dig below the surface? The good news is Audrey Phillips provides a platform through her Seattle-based company, 365 Meaningful Conversations. Audrey hosts a series of events every month all about finding these elusive meaningful connections. “You can really connect & meet people without awkward small talk” Audrey says. “We’ll use boxes of meaningful conversation-starting cards that I’ve designed. They spark conversations below the surface about topics like self-love, failure, happiness, relationships, etc.”

With 365 Meaningful Conversations, you can meet interesting people and skip the small talk. As the name suggests, the events are all about meaningful interactions where you get an opportunity to genuinely connect with people and talk about things that matter. From the lens of an immigrant, this initiative is really cool and much needed in the city. We caught up with Audrey to find out more about how the events work, her journey so far and big plans for the future…

Image by Audrey Phillips


1. Tell us a little about your growing up days?

I grew up in Woodinville, just east of Seattle. I’m the youngest of four siblings and always was a sensitive soul who loved running, listening to people, and playing outside.

I started to understand the epidemic of loneliness from the stories people shared and realized how these events created a safe space for people to connect.


2. What led you to start 365 meaningful conversations?

The journey of creating the box of 365 meaningful conversation-starting cards was a serendipitous series of events. It all started at a young age with my love of quotes & doodling. I got the idea to make a set of quote cards from a nature program and I spent two years hunched over in my free time at coffee shops…and I ended up drawing 365 quote cards! I started working as a wilderness therapy guide after college, which was jump-started by a fifty-day wilderness course with Outward Bound. We rafted 100 miles down an icy river, summited mountains in blizzards and scoured rock formations climbing.

I took copies of my quote cards along the journey and we’d read one before each meal (an Outward Bound tradition). My curated quotes sparked deep conversations as we ate beneath the stars. The culmination, of course, was a 3-day solo without food to contemplate the entire experience—and I spent the solo writing meaningful conversation questions on the back of each quote card and then I drafted my goal of hosting meaningful conversation events all across America (*the original dream was to live in a van and travel the US). I continued working on the cards while working as a wilderness therapy guide and a year later launched a crowd-funder where I raised $10k to get boxes of the cards manufactured!

I used my conversation cards on my wilderness therapy trips with at-risk students and was struck by how people craved spaces to talk openly. I started hosting meaningful conversation events on days when I wasn’t taking at-risk kids backpacking: 3 people came the first week, then 4 people, then 10 people, and soon enough, 30 people flocked to attend events. I started to understand the epidemic of loneliness from the stories people shared and realized how these events created a safe space for people to connect. I moved back to Seattle to go full-time on starting my business: Heart-to-Heart.

3. What do you think is the key to having a meaningful conversation?

I think there are five components to having a meaningful conversation—which I’ve defined as any conversation where you leave feeling seen & heard. I think a meaningful conversation starts with someone sharing vulnerably & authentically—stepping out of their comfort zone to share parts of themselves that they might otherwise mask, which requires courage! Then, it’s the listener’s job to be compassionate and curious when listening—to ask questions to show that they’ve listened, to connect with “me too” and let the person know that they’ve been seen & heard in what they’ve shared.

4. Can you describe the kind of events you host?

People arrive and get a name-tag where they can fill out their name, plus mark on a scale how comfortable they are opening up as well as if they’re a talker or listener! People mingle and small talk with others for about 10 minutes. Then, everyone gets a colorful chip that tells them what table to sit at! I give an introduction where I share the story behind 365 Meaningful Conversations as well as “how to have a heart-to-heart”—be real, be you, be compassionate, be curious and be present. Then, I encourage people to open up the box and look through the cards—and pick their favorite five. They take turns asking questions and get to set the tone for their table—if they want to dive in deep and answer a question like, ‘What’s the rock bottom of your life?’ they’re invited to…or, they can opt to talk about other things like self-love, body image, family dynamics, etc.—there’s an endless flow of meaningful conversations!

People crave a space to connect so much, so people are extremely grateful for these events! They’re incredibly special and people are always exchanging contact information with others at the end of events because people actually connect with people at these events.

5. How has the response been so far?

People crave a space to connect so much, so people are extremely grateful for these events! They’re incredibly special and people are always exchanging contact information with others at the end of events because people actually connect with people at these events. It’s pretty magical to sit back and watch strangers come together and over 2 hours be hugging each other and making plans for next weekend! I’m not surprised by the positive feedback or desire for the space because I think every single human wants to have a space to share who they are—to be seen and heard—and these events offer that space, which no other place does.

6. What are your plans for the future with 365 meaningful conversations?

The plans for the future are bright & big! 365 Meaningful Conversations is going to start hosting events within businesses—because workplace loneliness is part of the epidemic of loneliness with most people spending a majority of their weeks in the office, it’s so important to feel connected there! Also, 365 Meaningful Conversations is starting to host events for schools—because again, the epidemic of loneliness is hugely present in schools and meaningful conversations offer up a space for people to truly start to connect with one another. Finally, 365 Meaningful Conversations is going to keep expanding in the greater Seattle area with the hopes of creating a membership program and eventually create a shared community space for people to come together to connect—it’s so important to cultivate a sense of community for people.

7. What could someone expect when they sign up for an event?

When people sign up for an event they should expect an evening of meaningful conversations where they can open up and truly connect with others. It requires often stepping outside of your comfort zone, but that’s where all the magic happens!