Couples bring decades of experience to their new — and hopefully last — restaurant
By Cory Schachtel | September 5, 2023
New restaurants never open when they’re supposed to, but the owners of Happy & Olive better hurry up, because people are literally banging on the door. As I walk up to the under-construction restaurant in Crestwood Centre, a woman approaches at the same time.
“Are they open?” she asks.
“Not yet,” I explain. “But soon.”
Throughout the interview, no fewer than 10 people walk up to the window, cup their hands against the glass and peer in. Andrea Olson, who owns the restaurant with her husband Frank (it’s named after his great uncle and his wife), sits next to the window. She seems to know, or at least recognize, most of the window gazers, and waits for their vision to adjust before holding up her fingers and saying “Give us another week — maybe two!”
The couple has been prepping this specific space for over eight months, but they’ve been preparing to start this kind of establishment from scratch for over a quarter century, since they started at (and eventually owned) Red Ox Inn. “It was 27 years, 12 tables,” Andrea says. “I was front of house, Frank was in the back, and we learned the business by doing it.” The couple worked hard, eventually had three kids, and then opened a new restaurant, Canteen, in their own neighbourhood in Westmount. “We weren’t business people opening a restaurant — we were restaurant people opening a new restaurant and actually working in our restaurants. And I think there’s a difference.”
Then came COVID, and with Red Ox needing major upgrades, operating two restaurants just wasn’t feasible, so they focused on Canteen. They couldn’t afford the space anymore, and they had to let it go too. It was heartbreaking, and frustrating, and the couple wasn’t sure if they’d ever restaurant again — until they heard about this spot in well-established Crestwood Centre, which “Frank and I always had our eyes on.”
Opening a restaurant is a daunting task, no matter how much experience someone has. But luckily the Olsons are not alone. Dave and Ann Jackson have lived nearby to them for 27 years (their kids went to school together), and ran the Wired Cup cafe next to Red Ox Inn for its last 22 years. “With the tiniest of kitchens, and a domestic electric stove, they were making their own bread, cooking and brewing coffee for a lot of people. And it was all consistently delicious,” Frank says of his partners and friends.
With the restaurant dream team complete, the couples set their sights on the new location. “We literally gutted the place,” Frank says. “There was no proper kitchen. There were no gas lines. There was no HVAC. Not even the bathrooms are in the same spot. We’ve changed every single thing except the windows and the door, because we couldn’t.”
Now that Happy & Olive is open, it’s really open. Monday to Friday mornings from 7 to 11:30 a.m., the Olsons are in cafe mode, serving breakfast sandwiches and muffins, then table-served lunch until 2 p.m. Happy hour runs seven days a week, 2 till 5 p.m., followed by dinner until 10 p.m. They sleep in a bit on weekends, starting brunch at 9 a.m. until 2p.m. Coffee is available anytime.
Andrea says that Canteen was open seven days a week in its early days, “But what has really driven us to be open seven days a week here is that during lockdowns, we were open, we were closed, we were 50 per cent capacity, we were takeout only — the hours were just crazy, and we weren’t alone. So when we came here we decided we want to be the neighbourhood place, we want people, when they think of us, to say ‘Let’s go there — we know they’re going to be open.”