The art of conversation: how to have meaningful chats with new people

If ever there was a moment for self-doubt to hijack your soul, it’s the prospect of speaking to strangers; or people you don’t know all that well. There you are, searching for something funny or brilliant to say – but always with the risk that the other person (whispers it) might not be responsive. On the other hand, that ability to hit it off with someone you’ve just met is also one of life’s finest pleasures – an experience all in itself. 

“It takes courage to speak to new people; it’s normal to feel a little bit nervous,” says Georgie Nightingall, London-based founder and coach at Trigger Conversations. What’s needed, ideally, is “time and space to connect, along with new stimulation”, she says, and an environment in which people generally are “open to meeting each other”.

This could be a Christmas party, a community event, or an overnight train to somewhere new. Wherever you happen to be, there are some tried-and-tested techniques you can use to help skip the small talk and dig deep with rich conversations. Here’s how:

Be creative with your opener

“I like to think of conversation as a treasure hunt for common ground,” says Catherine Blyth, author of The Art of Conversation. “Ask open-ended questions, which require more than a yes or no answer. If you haven’t got an obvious topic to go in with, look around you. You already have something in common: the place you’re in. Make an observation, tack on a question, and you have a ready-made conversation starter.”

Georgie, who is also a TEDx speaker, suggests that you should veer away from the “scripts” of day-to-day conversations that we’re used to (and likely bored by), to elicit deeper interactions. “Statements are amazing ways to start conversations because you’re inviting other people to notice things and get curious about their environment,” she says. “The statement of the context you’re in always changes, too, so it’s novel and stimulating. You could make statements about yourself (‘I’m dying for a coffee’), the other person (‘You look like someone who knows where the bar is’), or the setting that you’re both in (‘This is an awesome café, isn’t it?’).”

A conversation is a treasure hunt for common ground

If you do decide to ask a question, Georgie recommends asking about someone’s individual experience of facts; because facts alone can quickly make an exchange lifeless, and you don’t learn much. For example, in a travel context, rather than just saying “Where have you been?”, you might ask, “What place were you most surprised by?”. Or, “Did you try out the zip-line?” becomes, “Were you scared to be hundreds of feet in the air?”

Catherine also suggests asking for help as a useful route into a conversation. “Seeking advice is inherently flattering,” she says. “It is, though sleight of hand, treating the other person as if they are already a friend; but not in an intrusive way.”

Prepare to share

“A conversation is a dance,” says Georgie. “You can’t just expect to be the one that does all the questioning – you’ve got to give something back.” At a basic level, this could involve an echoing tactic, whereby you say something like, “You sound like an adventurous person”. 

“If someone shares a couple of things about themselves, reflecting back what you’ve heard can make them feel incredibly seen,” she says. “They’ll open up more as a result.” 

Think of it as a dance. You have to give something back

Moving beyond, giving back also means being prepared to disclose things about yourself. “There’s this term in improvisation called offers, or hooks,” says Georgie. “You need to give people interesting hooks to allow them to get curious about you. If you’re open enough to be vulnerable, it helps other people to be vulnerable, which creates intimacy and closeness.” 

Catherine explains that most conversations progress through a “staircase to intimacy” that involves first sharing facts, then opinions, followed by feelings. It’s worth taking it slowly, but equally, “If you keep it vanilla, and take no risks, then you stay in a safe space,” she says. By being more open about yourself, “You feel the crackle of interest and the conversational ball starts bouncing back and forth. You want to chase it. And the other person is alive to that, so you’ll both have fun.”

Get playful and curious

A good conversation is actually more of a game than a smooth transaction. And thinking of it in this way also dials down the pressure for it to be “good” or “successful”. 

“To build rapport, it’s best not to over-engineer things; just be yourself,” says Georgie. “If you’re confident in yourself, people actually pick up on the energy a lot; it makes them want to come near you and talk to you. It’s good to have a playful mindset. Recognise that the messiness of conversation is a real thing; experiment with it, and enjoy it. Then you can let go and allow yourself to wander, explore, and actually end up in much richer places.”

It’s best not to over-engineer things; just be yourself

From this perspective, chatting to someone new is something best approached as an open-ended adventure. Go in with an open mind and an acceptance that it could go anywhere. “Great conversation brings us into the moment,” explains Catherine. “It reminds us to be a tourist in our world, to revel in the specificities of thought and place, and to be curious.”

Build your skills like a muscle

No-one’s born with suave conversational skills, and equally, many people feel intimidated by the idea of approaching strangers. So, it makes sense to think of conversation as a muscle; one which you can continually hone over time, without reading too much into it. “I think sometimes we put too much expectation around what a ‘successful’ interaction looks like,” says Georgie. “A two-minute exchange can produce just as much joy and curiosity as a longer chat. And the success comes in you trying, rather than how the other person responds.”

If someone you try to speak to cuts you off, try not to take it personally. Their response says far more about them (not you), and it happens to all of us. “I haven’t recovered from the time I was introduced to a woman at a party, and she looked me up and down and said, terminally, ‘Yes, we’ve met,’” says Catherine.

On the other hand, even the most unpromising starts can develop into something amazing later on. “I met a guy at a work lunch,” Catherine recalls. “I found him so dumb-founding that I said nothing. Next month, we’ll celebrate our 20th wedding anniversary.”

The messiness of conversation is real; allow yourself to be playful

Georgie says developing a “warm-up”, whereby you have small interactions with hundreds of people – with no real expectation of an outcome – can be a great way to work on your conversational muscle. 

Stefan Hofmann, professor of psychology at Boston University, outlined a similar approach when he spoke to us about overcoming social anxiety. His technique, known as social cost exposure, involves overstretching yourself a bit, or making a fool of yourself, to deliberately prove that nothing bad will happen. “We tend to exaggerate the social costs of interacting with others,” he says. “There won’t be any arrests, or crowds ridiculing you.”

Above all, says Georgie, a good conversation may be about, “just about going for it, having that kind of ‘hot’ quality rather than lukewarm-ness. Be bold”. So go forth, be silly, make playful conversation – the adventure starts now.

Flash Pack is a group travel company that specialises in small group adventures for solo travellers in their 30s and 40s. Find out more about how we work, and our mission to build a global community of friendships. 

Got a story or adventure that could inspire a solo traveller like you? Tag @flashpack on social or email [email protected] to be featured.

Images: Flash Pack