Starting a conversation with someone new can feel like walking into a room with the lights off. For many adults, the idea of making new friends seems not just awkward, but nearly impossible. Yet, according to journalist and friendship researcher Anna Goldfarb, the real barrier isn’t our personalities—it’s the questions we ask. Goldfarb, author of Modern Friendship: How to Nurture Our Most Valued Connections, argues that most of us default to safe, surface-level topics that rarely lead to meaningful connection.
Goldfarb’s research points to a simple truth: lasting friendships are built on shared wonder about the world. That means talking about what actually matters to each person, not just what’s expected. She offers five practical questions that can help anyone move past small talk and into real connection. These aren’t magic scripts, but tools for finding common ground and opening up genuine conversation.
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Why These Questions Matter
Each of Goldfarb’s five questions is designed to bypass the usual social roles and get at what people really care about—what makes them laugh, what they’re passionate about, what they wish others knew. This approach lines up with research from evolutionary psychologist Robin Dunbar, who identified seven “pillars of friendship”: shared language, similar education, geographic proximity, common hobbies, moral values, musical tastes, and a sense of humor. The more pillars you share, the more likely a friendship will stick.
These questions help you spot those pillars without falling into the trap of talking about jobs or social status—topics that often shut down conversation or make people uncomfortable. Instead, they invite people to share what’s alive for them right now, making the exchange feel less like an interview and more like a real moment of connection.
The Five Questions That Build Connection
The first question: “What’s entertaining you these days?” It’s a simple way to invite someone to talk about their current passions, whether that’s a new hobby, a favorite show, or a quirky obsession. If you share the same interest, the connection is instant. If not, you can dig deeper: “You started balcony gardening? How do you keep your tomatoes alive?”
Next, instead of the tired “What do you do?” try “What’s taking up most of your time lately?” This question leaves room for work, but also for family, creative projects, or caregiving. It signals that you care about what fills their days, not just their job title. It also avoids awkwardness if someone is between jobs or in transition.
The third question taps into culture: “What have you watched, read, or listened to recently that you’d recommend?” Relationship expert John Gottman calls these small invitations “bids”—the building blocks of emotional connection. Asking for a recommendation, and then following up later, gives you a natural reason to reconnect and keep the conversation going.
Fourth, humor: “Who or what makes you laugh the most?” This quickly reveals whether your senses of humor align, which Dunbar lists as a key pillar of friendship. You can follow up with, “Is there a comedian or Instagram account that cracks you up?”
The last question is the most personal: “What do you wish people knew more about you?” Goldfarb once asked this of her mechanic and learned he’d served in the Army in Germany in the 1960s, sparking a lively talk about German beer. This question invites vulnerability, but without pressure, and often uncovers important parts of someone’s story that don’t come up in daily life.
How to Use These Questions
Goldfarb doesn’t suggest rattling off these questions like a checklist. Instead, pick one or two that feel natural to you. Start with lighter topics—current obsessions, what’s occupying their time, or cultural recommendations—then move toward humor and, if the vibe is right, the more introspective question. Always balance asking with sharing: “Lately, I’ve been obsessed with…” That back-and-forth, repeated over time, is what turns a casual chat into a real friendship.
According to Top Santé, these strategies help adults break out of the rut of transactional conversation and build the kind of connections that last. The key isn’t to force intimacy, but to create space for it—by asking better questions and being willing to share a bit of yourself in return.
In the field of friendship psychology, researchers are increasingly focused on the mechanics of how adults form and maintain close bonds. Unlike childhood friendships, adult relationships often require more intentional effort and vulnerability. Studies show that shared activities, regular check-ins, and open-ended questions all play a role in deepening trust and emotional intimacy. For those who feel isolated or disconnected, learning to ask the right questions can be a powerful first step toward building a more connected life.
