They are the raconteurs, the wits, the storytellers. They bring the fizz and froth to parties and functions in the city.
In our culture of screens — where communication is waged by emojis — the art of conversation can sometimes feel like it’s in peril. And yet it’s still what makes the social sphere go ‘round, as the folks below know so well.
As we head deep into holiday-party season, Toronto’s liveliest talkers — the people you want to be seated beside at the dinner party — give us their advice on sparking meaningful, interesting conversation.
1. Edward Burtynsky, photographer
Edward Burtynsky‘s large-scale, bird’s-eye Earth images may sit in some of the most prestigious museums in the world — everywhere from the Guggenheim to the Tate — but the Toronto artist is not just one of the most important photographers in the world, he is also one hell of a storyteller.
Conversation tip
“These days, almost every conversation ends up in the same place — the mess we’re in: from climate change to the impacts of social media and AI to geopolitics. Instead of focusing on how everything is broken, I try to pivot to hope. Where do we still see it? What are the examples, the projects, the people that are making a difference? That’s the conversation I want to have.”
2. Adrienne Clarkson, former Governor General of Canada
There’s a reason the Right Honourable Adrienne Clarkson is a perennial in social Toronto. From her days as a CBC talk show host in the 1960s to her equally groundbreaking run as Canada’s 26th Governor General, to her advocacy work now, Clarkson remains forever curious, always game.
Conversation tip
“It’s important to ask people what they are doing right now, and from there you can always spin out the conversation. Everybody likes to tell you what they are up to. I meet people from all kinds of backgrounds and of all ages, and it is always interesting to hear their story.”
3. J. Miles Dale, film producer and director
Canada’s most ascendant producer and a regular collaborator with Guillermo del Toro — their latest film is the Jacob Elordi-starring ”Frankenstein” — Oscar winner J. Miles Dale lays it on dry.
Conversation tip
“I try to gauge the room. If it’s guys, I might turn to sports. In our business we tend to talk about … our business! And not gossip, just more about who is doing what. As for topics to avoid, with the increasingly divided society we seem to be inhabiting, it’s been risky to talk politics with actors or studio executives. Gotta be true to your beliefs but don’t want to step on a land-mine either!”
4. Samantha Nutt, founder of War Child Canada
Storied Canadian physician Samantha Nutt — who is also the founder of War Child Canada and a Canada Walk of Fame inductee — always tries to find moments of levity and doesn’t take herself too seriously.
Conversation tip
“In my experience, there are few things that can kill a conversation quite like ‘And what do you do?’ And there is nothing that quite crushes any festive mood faster than ‘I work in war zones.’ The reflexive move in a lot of starter conversations, for too many people, is to try to establish dominance or authority in some fashion, and they often don’t know they’re doing it, and it usually comes from a place of social insecurity: “I need everyone here to think I’m the smartest and most interesting person in the room.” But what it reveals is the opposite. If you spend more time talking about yourself, and what you think and believe, instead of asking questions and listening deeply, you’re instinctively less interesting to everyone else, because your intellectual incuriosity and vanity are on full display. I always start by asking other people about themselves: likes, dislikes, experiences. That will also identify any conversation traps — their ideological leanings, cultural reference points, shared points of interest. And create space for humour and honesty.”
5. Nicholas Mellamphy, creative director
A self-styled “glamour enabler” and a “harbinger of style in Canada” (according to Vogue), the former creative director of The Room at Hudson’s Bay adds a dash of naughty fizz whenever he makes the scene.
Conversation tip
Mellamphy has two easy topics for livening conversation: “Hollywood gossip and movie stars! Two things that I find will prick up some ears, and that I often lean on. And know your audience. That’s probably the most important thing, in tailoring your approach. Understand the assignment. Something also to keep in mind when going into a conversation: Everyone is human. No matter if you’re a foreign dignitary, a CEO, or a stay-at-home mom, everyone has had struggles, has insecurities or is excited about something. Something that often works, too: asking people about their travels. Where they’ve been or would like to go. This can give people an opportunity to tell you something about their tastes, their family. It opens up the conversation.”
6. Lauren Holly, actor
Lauren Holly, who appeared in “Dumb and Dumber” and “White Picket Fences,” has called Toronto home for many years, is always a loquacious delight.
Conversation tip
When in doubt, talk sports, she says. “I’m such a diehard Leafs and Jays fan.” Another way to bond is by talking family, Holly says. In her case, the three boys she adopted. “I always knew I was going to adopt. I saw an after-school special about it when I was a kid, and it stuck with me … They’re all within a year apart. My second two are fully biologically related. When I had three under three, I thought: OK, I have my family. They were meant to be brothers and meant to be mine.”
7. Renesha Monaco, content creator
One of the new “kids” on the social circuit these days, this content creator and founder of Sobar Social Club, an alcohol-free event agency, makes an impression. It’s the statement colourful hair, a certain fearlessness, but it’s also the warmth she brings.
Conversation tip
“My goal is always to make people feel seen. A genuine compliment, eye contact and a moment of real presence. I avoid topics that close people off or dim the room: anything too heavy. A party should be a space where people can expand, not shrink. Joy creates openness — and openness is where real connection begins.”
8. Jacob Martin, mixologist
Toronto’s mixologist of the moment has heard a lot of talk over the years, and like the best bartenders, he can amuse just as well as he can shake and stir. Known for his years at Bar Banane (and a previous life as an opera soprano), he can now be found at his hot new boîte in Yorkville, Powder Room.
Conversation tip
“I have served literal stadiums of people and witnessed an Everest of first dates, so believe me when I tell you: People suck at talking. And while some of this is because we have slowly become more introverted, the chief culprit is the smart phone.” So put that away, he says. “Great conversation is earned, and there is only one currency to buy better conversations … vulnerability. If your protagonist is one that brags, I have bad news: Ya boring. So tell a story where you lose. Tell someone about a time when things did not go your way.”
9. Carolyn Harris, royal historian
A royal historian, author, university instructor and frequent pundit, this Toronto academic is always ready with a sparky sound bite on the Windsors and all things royal.
Conversation tip
“I recommend open-ended questions that bring everyone into the conversation. Ask people about their travel, for instance. Questions about hobbies, interests and proud moments in life also get people talking in any setting.”
10. Liloo Alim, former Four Seasons Hotel concierge
One of Toronto’s most beguiling characters — best known for her time as the concierge at the Four Seasons for nearly four decades — the pocket-sized OG makes people smile whenever she enters a party.
Conversation tip
“If my time as a concierge taught me anything, it’s that we all carry stories worth hearing,” says Alim. Her overarching counsel: “It all comes down to asking questions. And listening. You generally get out of a conversation what you put into it.” Like, an experience she had recently in Barcelona when “a writer friend asked me to carry a book for an illustrator based there. I didn’t know the person, and was thinking it’ll be a quick cup of coffee and I’d hand over the package. Before going there, I had lost my beloved cat, Marty and when I met this artist, he was a bit teary-eyed because he had lost his little dog, Nuka, the day before. We ended up talking for hours about the loss of our pets. Grief connected us. ”
