Toronto Through the Eyes of Ashleigh Dempster and Amanda Blakley

Ashleigh Dempster and Amanda Blakley need little introduction. The sassy, smart and enviously stunning pair run The Society, a Toronto-based members-only club for the creative set (or, of course, those who really want to run in that circle). From the annual Boobyball and S.M.U.T Soiree to their Yogart series, the cultural curators have transformed the way people can experience and engage with the city.

Since they began The Society a few years ago, the club has grown from only a few members to hundreds. Their events have grown too, from intimate dinner parties to scotch tastings at Raptors' games, and exclusive polo or sailing lessons with experts in the field. The lovely ladies have even used their curating skills to expand the club to New York City. It all means we've only just begun to hear about the clever events they can concoct.

I caught up with the pair to discuss how they met, why they love Toronto and their favourite places to eat in and around the city.

How did you two meet?

We met in Bangkok through a mutual friend in the spring of 2001 and later that summer we traveled to Laos together. We shared some outlandish adventures during our travels and after returning home found a cute little apartment off College street and became roomies.

Why did you come up with the idea for The Society?

The simple answer is that we were socially bored and culturally stifled. The more long winded response is that we were searching for a bit more meaning in our night's out. Sick of going to the same bars and spending our small disposable incomes on bar tabs and shopping - we saw an opportunity to create unique cultural experiences that were equal parts affordable, approachable but still cool and relevant to our lifestyle.

What kind of events does The Society throw? What's been your favourite so far?

We call our events "Cultural Encounters" - everything has a cultural focus but with a unique twist making it relevant and approachable for a young, interesting and interested member base. They can range from offbeat literary salons in the park, to graffiti art tours on bicycles, or classical music in an underground warehouse. Favorites to date? Hmmm... hard to pick but The Great Debate with Mark Kingwell in Toronto and the foodie crawl (in SUV's) around Manhattan would be at the top of our list!

Neither of you grew up in the city, but moved here later on in life. What's the best part of moving from a small town to a big city?

Access. We're both small town girls at heart but the access you have in a large city can't be beat. Both of us are always on the hunt for new and exciting experiences. A big city provides a level of exploration for the culturally curious that a smaller town just doesn't offer. We love checking out new gallery exhibits as well as performances at the TSO, National Ballet, COC. We also eat out far too much!!

Being the party-planning ladies you are, what are some of your favourite hangout spots in the city?

Outside of work events, we crave low key and cozy places. Anything that's fun, chill and makes you feel like you are at your friends home! We love Le Petit Castor for their poutine, roasted chicken at Rosedale Diner and Amber for late nights!

Describe how you would spend an ideal weekend in the city?

Sleeping as late as possible then heading out for a long lazy brunch followed by a fun activity in the afternoon, i.e. tennis, picnic in the park, shopping, a matinee, etc. We rarely go out on the weekends so the evenings are usually spent over a dinner party with close friends.

What are your favourite places to eat?

For brunch, Harbord Room, Saving Grace, School and Mildred's Temple Kitchen.

For lunch, Terroni at Yonge & St. Clair, Patachou, Le Paradis as it's right next door to our office or Caffe Doria.

For dinner, Julie's Cuban, Senior's Steakhouse, Le Select, Table 17, Delux, OddFellows, TOMI-KRO and Capocaccia.

When you think of Toronto, what three words come to mind?

Emerging. Creative. Unassuming.

How do you get around the city?

In the summer we drive Vespas from Motoretta. Come fall, we put the Vespa's to bed for the cold weather and ride our matching black Dutch Batavus bikes from Curbside Cycle.

What makes Toronto a good place to party?

The people. The more we travel the more we realize how incredibly friendly and warm this city is. We're a refreshing, non-jaded bunch who work hard and play hard. Lately, we've noticed that the parties are loosening up a bit too which is fun. Yes, you can be in a pretty cocktail dress at a fancy party but that doesn't mean you can't cut some major rug on the dance floor!!