Audrey Phillips is not great at small talk. She’s more of a listener. People have always felt comfortable sharing their stories with her. Once, she was seated next to an older man on the plane from Seattle to New Jersey. She asked him how he was doing. They ended up talking about his divorce for the rest of the flight. Phillips was 15.

Another time, when her car wouldn’t start, Phillips checked in with the woman on the phone from AAA roadside assistance. “It seems like you’ve had a hard day,” Phillips remembers telling her. She had. They talked for two hours about the woman’s daughter and her brushes with the criminal justice system.

For friends and family of the former ski instructor and wilderness guide, it came as no shock that she would carve a job out of skipping the small talk to go straight to what matters. With her one-woman-business, 365 Meaningful Conversations, Phillip’s doing that by organizing events where people “can genuinely connect.”

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Guests, seated at tables of 4 to 6 people in local breweries, coffee shops, and restaurants around Seattle, pick quotes and questions from a set of 365 brightly-colored “connection cards” created by Phillips. Questions like “How do you make a difference in the world,” “What was the last mistake you made” or “What’s the story of your heartbreak,” are meant to help bypass the “Where are you from?” and “Where do you work?” chatter. There have been 4 of these $20-ticketed “heart to heart” events in Seattle; the next one on Capitol Hill is scheduled for March 19th at The Lab at Ada’s.

“Most of us want to go beyond the small talk and get to know someone on a deeper level,” says Phillips. “So I’m making the a to dive right in to more meaningful conversations.”

On paper, going from Colorado wilderness therapy guide to event organizer might sound like a stretch. To Phillips, it’s the same thing: Spending time with people, make sure they connect, and “listening to hear, not respond.”

The idea of question cards came to her during a wilderness training and snow camping trip in the Three Sisters Wilderness. Every  night, the group read a quote —about grief, or love, or anything else— from the stack of “quote cards” she’d made for herself in college the year before. During the three-day solo survival leg at the end of the trip, Phillips sat under her tarp for three days, and wrote questions on all of the cards.

Nearly two years later, the stack had grown substantially. A crowdfunding campaign helped her pay for the manufacturing of 500 boxes of 365 cards, by the same company that produces the game Cards Against Humanity. “The difference is that I’m doing this for humanity,” Phillips quips.

It was only after moving to Boulder that everything clicked. “I didn’t know many people there,” Phillips, who’s from Woodinville, says. “I think I even googled: ‘how to make friends in Boulder.’”

“I decided I’d organize the event I wanted, and see if people would come.”

They did. Over the summer, the attendance of the weekly Heart-to-Heart events, which used Phillips’ question cards as prompts, had swollen to around 30 people. At the final event, one of the regulars cornered her: Could she please keep doing this, perhaps not take that dream job?

Phillips being Phillips, she listened. Since moving to Seattle this January, she’s been working to get her business off the ground from her north Capitol Hill apartment. She says she’s not feeling the Seattle Freeze: “I think it’s hard to meet people anywhere, for a variety of reasons. People would rather swipe on their phones or stay in to watch Netflix instead of meeting people and talking to them. That’s not limited to Seattle. It’s hard to meet people, period.”

Phillips says 365 Meaningful Conversation events are not “a dating thing” because of the pressure this would bring.

With her focus on friendship, Phillips joins a budding “friend-making market” in Seattle. Public radio station KUOW recently started hosting “Curiosity Club Pop-Up” dinners for strangers based on a guiding question, and local newsletter The Evergrey recently partnered with Connect Lounge to create a new monthly speed friending event.

“There’s no doubt a need for people to meet in Seattle,” says Phillips. She’s hoping to soon scale up to one Meaningful Conversation so that pockets of neighborhoods can host the events on their own on a subscription basis.

At this point, nearing the end of our conversation, I ask Phillips to choose from some cards I’ve randomly pulled out of the box of cards.

“How do you define empathy? How is it different from sympathy, pity and compassion?” is the card she picks.

“It’s looking at one another with your heart, not your eyes,” she answers somewhat hesitantly — she’s used to other people answering questions. “When someone says they had a bad day, pity would be to say: ‘Oh, I’m sorry.’ I think an empathic response would ask: ‘How has it been bad?’ That allows for a connection, space for me to listen and care. Compassion usually includes feeling compelled to do something to help the situation. But sometimes nothing can be done. Often, listening is helping.”

You can learn more and find upcoming event dates on 365meaningfulconversations.com