Conversation tips from Toronto’s social scene stars

As the holiday party season approaches, Toronto's liveliest conversationalists—the people you want to sit next to at a dinner party—give us their tips for striking up meaningful, interesting conversations.

Edward BurtynskyLarge-scale, bird's-eye views of the Earth may be found in some of the world's most prestigious museums—everywhere from the Guggenheim to the Tate—but the Toronto artist isn't just one of the world's most important photographers, he's also one hell of a storyteller.

“These days, almost every conversation ends in the same thing – the mess we're in, from climate change to the impact of social media and artificial intelligence to geopolitics. Instead of focusing on how broken everything is, I'm trying to focus on hope. Where are we still seeing that? What are the examples, the projects, the people that are making a difference? That's the conversation I want to have.”

There is a reason, Venerable Adrienne Clarkson is a constant in social Toronto. From her days as a CBC talk show host in the 1960s, to her equally groundbreaking performance as Canada's 26th Governor General, to her advocacy work now, Clarkson has always remained curious and always entertaining.

“It's important to ask people what they're doing now, so you can always continue the conversation. Everyone loves to tell you what they're doing. I meet people from all different backgrounds and all ages, and it's always interesting to hear their stories.”

Canada's most rising producer and frequent collaborator with Guillermo del Toro, their latest film is “Jacob Elordi” starring Jacob Elordi.”Frankenstein– Oscar winner J. Miles Dale lays on dry.

“I'm trying to assess the situation. If it's guys, I might turn to sports. In our business, we tend to talk about… our business! And not gossip, but more about who's doing what. As for topics to avoid, given the increasingly divided society we seem to live in, it was risky to discuss politics with actors or studio heads. Gotta be true to my beliefs, but don't want to step on a landmine either!”

Legendary Canadian doctor Samantha Nutt — who is also the founder of War Child Canada and a member of Canada's Walk of Fame — always tries to find moments of levity and doesn't take herself too seriously.

“In my experience, there are a few things that can kill a conversation, such as: “What are you doing?” And there's nothing that ruins the holiday spirit faster than saying, “I work in war zones.” The reflexive step in many initial conversations for too many people is to try to establish dominance or authority in some way, and they often don't realize they're doing it, and it usually comes from social insecurity: “I need everyone here to think I'm the smartest and most interesting person in the room.” But what it shows is the opposite. If you spend more time talking about yourself and what you think and believe, instead of asking questions and listening carefully, you instinctively become less interesting to everyone else because your intellectual incuriosity and vanity are on full display. I always start by asking other people about themselves: what they like, what they don’t like, what their impressions are. This will also allow you to identify any pitfalls in the conversation – their ideological biases, cultural references, common interests. And create space for humor and honesty.”

A self-proclaimed “glam stimulant” and “Canada's harbinger of style” (according to Vogue), the former creative director of Room on Hudson's Bay adds a bit of zesty sizzle whenever she appears on stage.

Mellamphi has two simple topics for lively conversation: “Hollywood gossip and movie stars! Two things that I believe will prick up the ears of some, and which I often lean on. And know your audience. This is probably the most important thing in choosing your approach. Understand the brief. Something else to remember when entering into conversation: everyone is human. It doesn't matter if you are a foreign dignitary, a CEO or a housewife, everyone has had difficulties, uncertainty or being excited about something. Something that also often works: asking people about their travels. This can give people the opportunity to tell you something about their tastes, their family.

Lauren Holly, who starred in Dumb and Dumber to White Picket Fence, has called Toronto home for many years and is always admired.

“When in doubt, talk about sports,” she says. “I’m such a die-hard Leafs and Jays fan.” “Another way to bond is to talk about family,” says Holly. In her case, these are three boys whom she adopted. “I always knew I was going to adopt a child. When I was a kid, I saw an after-school program about it, and it stuck with me… They're all a year apart. My other two are completely biologically related. When I had three kids under three, I thought, OK, I have my family. They were supposed to be brothers and they were supposed to be mine.”

One of the new kids on social media these days, content creator and founder of Sobar Social Club, an alcohol-free event planning agency, is making an impression. There's the striking bright hair, a certain fearlessness, but also the warmth that she brings.

“My goal is always to make people feel seen. A sincere compliment, eye contact and a moment of real presence. I avoid topics that shut people out or darken the room: nothing too heavy. A party should be a space where people can expand, not contract. Joy creates openness, and openness is where real connection begins.”

By now, the Toronto mixologist has heard a lot of talk over the years, and like the best bartenders, he can entertain as well as he can shake and stir. Known for his years at Bar Banane (and previous life as an operatic soprano), he can now be found at his hip new Yorkville restaurant, the Powder Room.

“I've served literal stadiums of people and witnessed the Everest of first dates, so trust me when I tell you: people are bad at talking. And while part of that is because we're slowly becoming more introverted, the main culprit is the smartphone.” So leave it alone, he says. “Good conversations are earned, and there is only one currency that can buy the best conversations… vulnerability. If your protagonist is bragging, I have bad news: well, boring. So tell a story where you failed. Tell someone about a time when things didn't go your way.”

A royal historian, author, university lecturer and frequent pundit, this Toronto-based academic is always ready to speak powerfully about the Windsors and all things royal.

“I recommend open-ended questions that get everyone involved in the conversation. For example, asking people about their travels. Asking about hobbies, interests, and proud moments in life also gets people talking in any setting.”

One of Toronto's most attractive heroines, best known for her work as a concierge at the Four Seasons Hotel for nearly four decades, pocket O.G. makes people smile every time she comes to a party.

“If being a concierge has taught me anything, it’s that we all have stories worth hearing,” says Alim. Her general advice: “It comes down to asking questions. And listening. You usually get out of a conversation what you put into it.” For example, an experience she recently had in Barcelona when “a writer friend asked me to bring a book for an illustrator working there. I didn't know the person and thought it would be a quick cup of coffee and I'd drop off a package. Before going there, I lost my beloved cat Marty, and when I met this artist, he was a little teary-eyed because the day before he had lost his little dog Nuka. We ended up talking for hours about the loss of our pets. Grief bound us.”