Weddings
From Friend Zone to the Front Row
Inside Emily Naddaf & Josh Lerner's East Coast Wedding
Some love stories begin with fireworks. Others begin with an Arkells concert, a mutual friend’s living room, and impeccable timing. Emily Naddaf and Josh Lerner first crossed paths in the summer of 2017 at a pre-concert gathering before an Arkells show. Emily was in a relationship at the time, so any sparks were politely filed away for later. Still, something lingered. They laughed. They talked. They became friends.
“He was hilarious,” Emily recalls. “Josh had this infectious energy that filled the room. He could make anyone laugh — deep, belly laughter. And he had that rare mix of confidence and charm you don’t forget.” Josh remembers his first impression of Emily just as clearly. “She was joyful,” he says. “The life of the party — buzzing around, talking to everyone, incredibly smart. Emily can hold her own in any conversation.”
By December, timing finally caught up with chemistry. Both newly single, Emily and Josh began lingering over lunches, staying out late, and texting just enough to keep things interesting. Eventually — after what Josh might call strategic persistence — Emily agreed it was time to officially move him out of the friend zone.
Despite overlapping social circles and countless group hangouts, their first proper date didn’t happen until six months after they met. Dinner was at Noce, an Italian restaurant in Toronto’s Trinity Bellwoods neighbourhood. They laughed, learned more about each other, and then, in classic Emily-and-Josh fashion, left dinner to attend a mutual friend’s birthday party.
As their relationship deepened, life got busy. Josh practiced law at Lerners LLP, while Emily, a Director at the Wealthsimple Foundation, poured her energy into work and community-building. Whether hosting dinners, organizing fundraisers, or planning their now-legendary annual Chrismukkah party, community has always been Emily’s north star.
For Emily, knowing Josh was her person wasn’t a lightning-bolt moment. Instead, it arrived as a quiet accumulation of certainty. “There was just a growing sense of ease,” she says. “Everything fit — our friends, our families, our lives. About five months in, I told a friend I thought we’d get married. It sounded wild at the time… but here we are.”
Josh’s realization came during the quieter stretches of the pandemic. In 2020, the couple isolated together in rural Nova Scotia at Emily’s family home, and later at Josh’s family cottage in Grand Bend. “We’re both incredibly social,” he says. “So when it was just us — and it still felt great — I knew.”
Josh proposed in 2023 over Thanksgiving weekend at Gaffs Point in Kingsburg, Nova Scotia. After hiking to a secluded beach just off the main trail — one they had discovered together during COVID — he asked Emily to marry him. They celebrated with lukewarm beer (the Rose Bay General Store was, regrettably, out of champagne), soaking it all in before sharing the news with their families.
On July 12, 2025, Emily and Josh were married at the Chester Golf Club, surrounded by 110 guests. They envisioned an event that felt elegant yet unfussy — an elevated East Coast celebration grounded in hospitality and joy. Much of the décor was designed and created by Emily’s family, lending the weekend a deeply personal, familial feel.
With prints, patterns, and colour encouraged, the celebrations began with a welcome party inspired by a traditional Scottish ceilidh, complete with fiddle players, seaside group dancing, and lobsters to kiss — a playful nod to the East Coast tradition of getting screeched in.
The rehearsal dinner unfolded on the water, with lobster rolls served during an evening sail. A thread of whimsy carried through the weekend thanks to a custom logo of lobsters in formalwear — serving wine and cupcakes — which appeared on wine labels, signage, and other thoughtful details.
The wedding ceremony was officiated by best friend Suzanne Tillmann alongside Justice Joshua Arnold, who guided guests through meaningful Jewish traditions. Set outdoors, the ceremony was framed by florals that felt entirely of the place — an artful mix of garlic scapes, smokebush, alliums, and sweet peas. Emily’s standout bouquet featured bright yellow oncidium orchids flown in from Holland, a joyful echo of her engagement ring.
Before dinner, guests were treated to one of the day’s most memorable moments: a surprise band set that sent the dance floor into near structural collapse.
Dinner reflected both place and personal history. Guests enjoyed oysters, shrimp, fish, and scallops, alongside nods to the couple’s roots — Chicago 58 salami and spinach fatayer. Dessert came courtesy of the couple’s talented friend Olivia (@trickdough.hfx), who created both the wedding cake and donuts.
Each guest received a handwritten note with a shared core memory — a small but powerful reminder of the relationships that shaped the couple and carried them to this moment.
Emily and Josh postponed their honeymoon until this month, when they’ll trade the Canadian winter for South Africa. A fitting next chapter for a couple who have always believed that the best things — love, community, and a life well-hosted — are built slowly, thoughtfully, and together.
Emily + Josh's favourite gifts
"We're big sleep hygiene people and love to get a proper night’s shut eye as often as we can. This bedding is soft, understated and luxurious. The pom details on the sheets are so charming!"
VENUE: Chester Golf Club PHOTOGRAPHER: Rebbeca Frank COORDINATOR: Yours for the Day CONTENT CREATOR: Style with Christie FLORIST: Lovie and Sons Flower Co. HAIR AND MAKEUP: Alyssa Thomas Makeup; Selena Makeup RENTALS Element Event Solutions East OYSTER BAR: Cams Coastal Catering CAKE AND DESSERT: Trick Dough DJ: Andrew Tufts BAND: Merimac Music
