Emily + Josh by Rebecca Frank

We wanted something that was unexpected, to bring an element of cool to a classic setting.

Tell us a little about yourselves, what you do, what you love…  

Josh and I come from different backgrounds and hometowns, but looking back now, it’s almost inconceivable that it took us so long to meet. We’re both incredibly outgoing, with an expansive and overlapping community in Toronto.

Josh is a partner at Lerners LLP, a law firm, and I oversee social impact work at Wealthsimple, a Canadian fintech. Our free time is taken up with lots of trips, and staying active with an equal balance of exercise and entertainment – we pride ourselves on having a warm home and are known in our circles for regularly opening it up to our friends and family.  

How/where/when did you meet – and what were your first impressions?  

We met in the summer of 2017 at a mutual friend’s gathering before a concert. At the time, I was in a relationship, so the timing wasn’t quite right, but we became friends and stayed in each other’s orbit. By December, we were both single, and after months of lunches, nights out, and long text exchanges, Josh eventually convinced me to give him a real shot.

My first impression of Josh was how effortlessly he could captivate a room. He had an uncanny ability to make people laugh and a confidence that at the time, I mayyyyy have thought bordered on arrogance, but I came around quickly.   Josh later told me he saw me as joyful and magnetic, bopping between conversations, sharp, curious, and very much myself.

What started as a friendship loudly unfolded and publicly, in front of all of our friends over New Year’s 2018 on the dance floor. That PDA turned into something deeper, grounded in ease, humour, and a sense that we simply fit.

What styling and visual elements worked best for you? (could be things, the florals, particular hire products or your marquee, etc., something the stylist created or simply just the scenic beauty of your location or the existing design of your venue).   

From the beginning, we thought deeply about the guest experience. The vision was elevated East Coast — generous hospitality paired with thoughtful, playful personal details. We wanted to bring our community to a place that felt so special and instinctive to us (it’s where Emily’s family is from!) but was brand new to many of them.   

From customised wine labels, a one-of-a-kind bar and seating chart built by Emily’s brother and stepfather, to hand-painted signage by Emily’s mother, everything felt intentional and connected. We also created a mascot, a lobster in formal wear drinking wine, who showed up across all print materials – including handwritten notes for each guest.  

The florals also made the day. We gave Bri, our florist, a brief that included the phrase: “seaweed on land”. We wanted something that was unexpected, to bring an element of cool to a classic setting. She delivered. Lots of local ingredients that felt sculptural and contemporary: garlic scapes, foxglove, alliums and green smokebush. For my bridal bouquet, she paired bright yellow oncidium orchids and sweet peas, in a thoughtful nod to my engagement ring and my childhood nickname.   

These elements, against the expansive views of Chester’s famous sailing seas, made the day feel timeless.

What did you enjoy most about the planning process, and do you have any tips for couples starting their wedding planning journey?  

Planning our wedding was a constant joy and also, a constant stress… We’re known for hosting lots of parties, and we’ve been to a ton of weddings, so I (Emily) wanted to really make sure that if we were asking our guests to fly across the country, they would be REALLY happy they did.   

Consider the guest experience: Think carefully about what you want your guests to feel. Ensure no one is ever hungry, thirsty or bored. It’s not about the budget; it’s about the care and consideration. Plan unexpected surprises, personal touches, and leave room for kismet.   

Imagine little rituals or moments that will keep people engaged and the energy up. We had funny personalized props and gave them out to friends on the dance floor, we had table captains keeping the drinks flowing, everyone was always laughing and dancing.   

As much as it’s “your” day, everyone else spent money and time to be there; if you make sure they’re having the best time ever, it will add to your memories and experience.   

Time the music: We went from big band during cocktail hour, to disco for dinner, to Celtic classics to kickstart the dance floor and university club throwbacks for late night. Music is the magic ingredient that sets the pace.

Tell us about your vendors. Were there any standout suppliers you would like to make special mention of?   

We wouldn’t call them vendors; they were more like partners. I feel like we’ve created friendships – some of my most active DMs are still these with gals months later.

Rebecca Frank. I mean… c’mon. You can’t get any better. Rebecca blended into our wedding like family. We had her for three days: the rehearsal, the welcome party and the wedding. She got right in there with us, hanging off the side of a sailboat, jumping up and down on the dance floor, literally rolling on the grass to get our sunset shots. We have so much gratitude for her – even if the photos had been bad, we wouldn’t have had any regrets about hiring her, but they ended up far surpassing our highest expectations.   

Lovie and Sons Flower Co., Bri has an impeccable eye and great taste! She worked so closely with me on the floral design to make sure I felt great about it. She extended me (and my mom, who is a big floral aficionado) a lot of patience and grace, and I will always remember gasping when I saw the space walking into the venue for the first time.   

Yours for the Day. Coordinated all of the details and made my incredibly particular vision come to life. I had so many little curated moments, notes, ideas, visions… Leah and her right-hand, Steph, made it all happen (Despite a lot of wind and quickly changing weather!) We didn’t worry about a thing on the day of; they handled it all with grace and poise, and we got to be fully present during our day. We’re so grateful for that.   

Trickdough. We have a bunch of mutual friends, and I’d heard rumours about her exceptional skills in the kitchen, but I’d never tried her cake before hiring her. I knew from Instagram she could nail the vision, so I reached out. Then a few months later, I’d flown out for a site visit and ended up at Olivia and her partner Raxx’s home for an impromptu kitchen party. They are so warm and inviting. She had some leftover cake set out casually in a takeout container, and I took a bite, and my mind was blown.   

The staff at the golf course were true MVPs. Somehow, our last bus of the night left the venue without grabbing the remaining 60 guests. We were stranded at 1:30 AM – no cabs, no cars – out on the coast. The staff all jumped into their vehicles, told us to all hop in and started doing runs back into town with guests in formal wear piled into the cab of their trucks. True East Coast hospitality made for a great memory.

Tell us about your main outfits, what was unique, and is there a story?  

I (Emily) tried on more dresses than any bride should. I wanted something I would look back on in the future with ease and the assurance that I selected “the one”. It needed to be elegant and enduring, and appropriate for our East Coast setting.   

I didn’t know it right away, but the dress grew on me. Looking back on photos from a trip to New York, I became hyper-fixated on a Monique Lhuillier number I had tried on. Thick lace, a removable bolero with a high neck, form fitting.   

I couldn’t justify the price tag for a few hours of wear, BUT I ended up finding it online, pre-loved at a bridal shop in Beverly Hills. I had it shipped to me the next day! It was perfect – I just had it taken in at the waist, but it was cut to my exact height already.   

I also leaned into something borrowed; my pearl earrings were from my husband’s dad’s partner, Andrea Hopson, who has exquisite taste. My veil and second dress were from a dear friend, Hinson Chaplin, and my purse was from my bridesmaid, Lauren.   

Josh’s suit admittedly was a bit of a last minute affair, but we picked out a Canali number together at Harry Rosen. We spent hours agonising over his tie. He also wore silver and blue convertible cufflinks I gifted him for Valentine’s Day, a nod to his other true love… his vintage Mercedes.

Tell us about your wedding and engagement rings.  

Josh led the design of my engagement ring, which exceeded all expectations. I always wanted something that felt unconventional but timeless. He surprised me with an emerald cut canary diamond, set with two trapezoid diamonds. Yellow is my forever favourite colour – to me, it evokes sunshine, positivity, and happiness.   

The ring has an heirloom quality, and we reflected together at the time that it would be a beautiful ring to keep in the family for the next generation. Truly, it is my all-time favourite engagement ring. (!!!!!!!)   

Our wedding bands were simple, from Mejuri, a Canadian brand we love. Although Josh lost his first one 3 days after the wedding in a run-in with a hornet’s nest.

What were one or two elements that were most important to you both that you were happy to spend a little more on? (food, photography, florals, the venue, your outfits?).   

Photography. Everyone told us how fast the day goes, and we both agreed we wanted to look back and not just have a record of the day but a recording of the most intimate, joy-filled moments. Rebecca has a unique eye and an uncanny ability to capture emotion in unexpected places. When we look back on the photos – the expressions, the laughter, the love – we feel it all over again.

Entertainment. We knew we wanted our wedding to be a party, so great music was a non-negotiable. We booked our band early; they are well known out east and played a mix of East Coast essentials and wedding classics. We hired an amazing DJ a few weeks before, because we realised our night would not be complete without a few rounds of Avicii. Do NOT skip out on entertainment; the music completely sets the tone for the night.

Was there a favourite moment (or two) that you will treasure always?   

Our entire ceremony was so different and fun, filled with contemporary takes on Jewish traditions and well-wishes from many friends and family, but my (Emily’s) aisle walk took the cake. One of my best friends, and bridesmaid, Lauren, said to me that morning: “Remember to pause and look around before you walk down the aisle. It happens so fast, take it all in!” So when I walked, I stopped to really see everyone and feel that moment fully. I kept starting and stopping and crying and laughing. Everyone you love, who has travelled to your favourite place in the world, outside in the ocean breeze, clapping and cheering. Inconceivable joy.   

The dance floor was also the best. We moved straight into our first dance before sitting for dinner, letting the energy crest instead of settling. It was electric. Our first dance was Mike Mains and the Branches’ cover of “I love you always forever” when the beat dropped, all of our friends and family ran onto the dance floor and just put their arms around us, jumping and screaming the lyrics. Our venue was in an older building, and looking back, honestly, we’re relieved the floor didn’t collapse. If you could bottle that feeling and sell it, you would be the richest person in the world.  

What does being married mean to you, and are there any special rituals you have that you would like to share?   

It’s been much more different than we anticipated – in that we didn’t think anything would change, and somehow everything did. We’d dated for almost eight years when we finally married, lived together for more than half of that time, so we figured married life would be an extension of that. But something switched for both of us.   

We’ve settled into this new routine of contentment and connectedness. Small rituals like reading together in bed each night, opening our bedroom door to morning light to greet the day, or calling each other throughout the day…. In making the active decision to choose each other in marriage, it feels like we’ve moved into a new moment in our relationship. One where the other areas of our life seem to have fallen beautifully into their rightful place.