A friend recently opened a group dinner with the topic “What’s one thing you’ve learned about yourself in the past year of your life?”. It prompted some awkward laughs and shifting in seats as we mentally shifted from chit chat and racked our brains on how we’d respond to such a question. Yet we engaged, and another friend shared that she’d had the confidence to leave her job and get a new one this year thanks to seeing me leave my job last year. She shared that my move had been the moment that she saw it was possible to leave and make that sort of change herself and it led to her having the confidence to take a similar step. Without the friend framing this conversation topic and encouraging the group to connect on a deeper level, I would’ve had no lasting memories from that meal, but instead I came away with a story about the impact I’d had on my friend’s life trajectory. These connections remind us that we matter.

Yet when was the last truly engaging conversation you had? If you’re lucky it was in the past couple of days, but you wouldn’t be in the minority if it was much longer ago.

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We’re starved of deep social connections in the world today. We spend more time on screens than ever before, remote work has sapped in-person connection, and we’ve turned to parasocial relationships with social media personalities as substitutes for increasingly rare real-world connections. With our busy lives and lack of regular hang-outs, finding time to meet with friends has become as painful as scheduling work meetings - I joke about playing calendar tetris with friends, a joke that originated in my life as a product manager at work. Yet when we finally meet up with a friend in a slot that’s been booked three weeks out, it’s all too easy for conversation to become formulaic, important life events masquerading as status updates in a meeting agenda. We’re desperate for deep social connection, and it’s lacking in our lives.

I think of social connection as where in conversation with someone else we learn something significant enough to form a tangible memory, the ability to look back weeks or months from that point and remember that conversation where you gained a deeper understanding about ourselves, them, or the world more generally. The more we understand the world and those within it, the stronger our ability to draw meaning from experiences. Each deep conversation adds another stepping stone on our path through life, extending our ability to explore the world and further connect with others, and for this reason we should treasure every opportunity to cultivate these connections.

When we’re starved of meaningful conversation, our wellness suffers. As an introvert, I feel the pain of surface level conversation acutely. One study has shown that the higher the percentage of conversation that is small talk, the lower the participants’ well-being, whereas the higher the percentage of substantive topics, the higher the well-being. Deep conversation is also often the only time that many of us get for introspection. In a world absent of journaling, conversation with friends helps us think and process our thoughts to discover how we feel, their reactions helping us process our situation.

Therapy has been embraced with open arms by the younger generation recently, at precisely the time where social connection has fallen to decade long lows. Therapy serves a purpose in providing professional input on situations we’re working through but it’s no replacement for true connection, a relationship conditional on payment doesn't meet human needs for mutual connection.

Making a change to experience deeper social connection more often can be scary, there’s comfort in the norms. But while these changes might feel uncomfortable at first, it’s worth pushing through that discomfort for the ability to connect with people on the other side. So how do we experience engaging conversations more often? There are four key components to consider.

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First, prepare. Think about what experiences you’ve had recently that you’d like to share and write a list of topics you want to discuss. You could create a Conversation Menu, where you write up a few questions for each course that can be used as prompts to help guide the conversation over dinner.

We have a faulty belief that preparation is bad or unnatural, and conversation suffers as a result. You wouldn’t decide what you’re cooking as your dinner guests arrive, and yet if we’re going around a friend’s house for dinner, we’ll spend ninety percent of our time deciding what to wear and what to bring, and topics of conversation are barely considered. 

Second, create an environment that’s conducive to connection. If you’re at home, get everything in place so everyone’s comfortable and doesn’t need to move around. If you’re dining out, consider waiting until the main course has been served and you’re free of interruptions before raising the conversation topic. This attention to environment matters because we're sensitive to environmental cues, from the music playing in the background to where we're seated and how we're lit - you wouldn't have a heart-to-heart at the break room table at work under blueish-white fluorescent lights. What would it look like to create an environment more conducive to social connection?

Third, go first. Introduce the conversation topic, confidently frame the discussion for the group, and offer to lead with your answer. Your answer can set the tone for the conversation, so consider leading with vulnerability - maybe something you’re grappling with at the moment that you’re open to receiving advice on. This opens the door for others to share their own experiences and develop meaningful connections together.

Fourth, lead with kindness. Think about what would help your conversation guests be more comfortable to open up. It might be to lighten the mood with good humor, it could be asking considerate follow up questions, maybe it’s just giving them space to take more time to think through their thoughts before sharing. I’ve often experienced friends not initially being ready to discuss the conversation topic when it’s first broached, but later in the evening they’ll proactively raise the conversation again after some thinking time, and these can be some of the most beautiful moments of connection that lead to deeper relationships.

These aren’t sure-fire approaches, you’ll want to adjust this based on your relationships with each person in the conversation. When I wanted to gain a deeper connection to my family over Christmas I bought The Hygge Conversation Game, a set of conversation cards to prompt conversation which had a friendly tone and some levity. The fact I'd bought the cards, instead of picking the topics myself, helped us skip any uncomfortable topics without feeling obligated to answer them. When I attended a Friendsgiving dinner, I placed conversation menus around the table which were only used for a couple of questions and that was okay, sometimes the mood isn’t there and introspective discussion shouldn’t be forced. What I’ve found particularly helpful is when I acknowledge there might be some discomfort and share that developing deeper connection is important to me - where this vulnerability has often been reciprocated with others' willingness to engage and beautiful conversations have come about because of it. 

Engaging conversation might not be easily found, but creating an environment for deep conversation can be surprisingly simple. Many of our conversation partners are eager to experience this connection; we just have to choose to prioritize it.