Real Weddings: Steph and Adam

Stephanie Holmes, a server and fashion-and-lifestyle influencer, and Adam Holmes, a producer, met on Twitter just over 11 years ago. After a whirlwind romance involving a spontaneous trip to Jamaica, the pair moved in together in late 2014. After they found out they were expecting a child, in the spring of 2022, Adam proposed to Steph during her pregnancy-announcement video shoot at Sunnyside Beach. This past June, Steph and Adam hosted a glamorous, retro-inspired 50-person wedding at the Darling Mansion. Here’s how it all came together.

Steph: Adam started following me on Twitter in early 2013. I don’t remember who sent the first tweet, but we exchanged a few messages. I was living in Kitchener, and Adam was bartending and doing video production for MLSE in Toronto. I was curious about his profile—he described himself as a cool producer working in New York, LA and Toronto. We were both in relationships at the time, so our exchange was very innocent.

Adam: After both of our relationships had ended and we’d been single for a few months, we started texting and then hanging out casually—going for walks in High Park or grabbing coffee. One day I posted a photo of a laundromat I was at on Instagram, and Steph happened to be just around the corner, so she surprised me with a visit.

Steph: During one of our texting conversations, Adam mentioned that he needed a vacation. He’s often off in February, when the NBA is busy with the all-star break, and it was a particularly frigid winter—the year of the infamous Toronto ice storm. A few weeks later, he casually asked me to go to Jamaica with him. I thought, Pardon?!

Adam: I was going to go regardless, so I shot my shot. I liked Steph a lot, and I knew we’d have a blast, so I threw caution to the wind.

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Steph: At first I thought he was out of his mind, but then I got excited about the idea. I figured, I’m single—I should be spontaneous. So I agreed. We booked the trip for early February, before we had even been on a real first date.

Adam: Before the trip, we did finally go on a proper first date, on New Year’s Eve of 2013. We went to the Beaconsfield (now Death and Taxes) for drinks. We were having so much fun chatting that we almost missed the countdown.

Steph: After midnight, we went to a friend’s loft party. The next morning, I headed back to Kitchener totally smitten.

Adam: In February, we took an action-packed five-day trip to Negril, Jamaica, where we stayed in a gorgeous cliffside hotel just up the coast from Seven Mile Beach. We were there for Bob Marley’s birthday, and good energy was flowing. It felt like a year’s worth of memories happened in that one trip.

Steph: Without prompting, two older ladies slathered us in aloe vera and then charged us for it (in their defence, we were sunburned). We ate amazing homestyle goat curry on the beach, hired a private driver who took us around in a beat-up Honda Civic and toured the most incredible waterfalls.

Adam: I remember the moment we both felt like we were falling in love but weren’t ready to say it yet. We were lying under a clear, starry sky, listening to the waves and talking. There was a long pause that we both knew meant “I love you,” but instead I just said, “Well, this is pretty cool.”

Steph: A few weeks later, I came into Toronto to celebrate Valentine’s Day with Adam, and he surprised me with a night at the Thompson Hotel and dinner at the Drake. He was in full wooing mode, and I was wooed. Everything happened so organically that I don’t know exactly when we decided we were official, but we exchanged I-love-yous that night.

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Adam: Over the next year, we took the bus to see each other every weekend. In a way, it was good to have the short distance between us to help us take things slow.

Steph: When my lease was up near the end of 2014, it made sense for us to find a place together in Toronto. We moved into a cute unit in a two-storey apartment just off of the Danforth.

Adam: For the first few years of living together, we were on opposite schedules. I started producing full time and would often wake up before 5 a.m. and see Steph as she was coming in from a late-night bartending shift.

Steph: When Covid hit six years later, we were suddenly spending all of our time together. I know some couples struggled with the intensity of that much intimacy, but being locked down together only reaffirmed how much we wanted to be together. When gyms started reopening, I’d even book our time slots together.

Adam: We were struck by how grateful we felt to still really love hanging out. That’s when we started to talk more about our future together. I’ve never been against marriage, but I didn’t grow up with a goal of getting married. My dad is Scottish, and seeing him experience strife during the Troubles also made me hesitant about the Catholic practice of marriage.

Steph: It was a bit different for me. I grew up in a Christian household where there was an expectation that if you dated someone, the goal was to marry them. As a little girl, I was surrounded by women excited to get married and become moms. So I was transparent from the start that I wanted to get married and have a child one day, but I didn’t feel rushed. I was confident that we were in it for the long haul.

Adam: Steph never put pressure on me—it wasn’t a put-a-ring-on-it-or-else situation.

Steph: In 2021, before getting married, we decided to have a baby. I lost three pregnancies before becoming pregnant with our daughter in the spring of 2022.

Adam: After that, I thought, It’s time. I gotta do the thing. Steph’s best friend was coming to Toronto in June to take photos of Steph on the beach for a baby announcement, and I decided to photobomb the shoot with my proposal.

Steph: I was distracted by the shoot, so when Adam got down on one knee, I was shocked.

Adam: I just looked up at her silently with the box open, tongue-tied—I thought it was pretty obvious that I was proposing. After she said yes, the beachgoers nearby gave us a standing ovation.

Steph: Right afterward, I saw the Chicks at Budweiser Stage, had tater tots at Pennies and swooned over my new ring. I was excited to get married, but planning for our daughter came before all of the wedding planning. We waited until she was born, in early 2023, to get started.

Adam: We half-joked about eloping, but we ultimately decided to have a wedding at a non-traditional venue in Toronto.

Steph: A friend of ours posted photos of a wedding at the Darling Mansion, a Victorian-meets-’70s-rock-and-roll venue in the west end. I know the owner, Tanya Grossi, and Adam and I had always wanted to host a party there, so we thought, Why not our wedding? The property’s style guided our aesthetic.

Adam: The small venue helped us keep it intimate. With two big families, it could have ballooned into a 400-person wedding, which we couldn’t afford.

Steph: I saw a blog post about a vow renewal ceremony in Vegas that was casual, retro and a little costume-y. Immediately, we knew we wanted a similar look for our wedding.

Adam: The guy in the blog post had a professional Western vibe, and I decided to go all-white to match Steph. MasterSupply in Markham made me a special custom white leather jacket with fringe, which was fun to wear on a sweltering June day. I also got white jeans, a white linen shirt and a bolo tie. We found my cream-coloured sombrero at AFC, a haberdashery in Kensington Market, and they reshaped the brim to give it a formal edge. I paired it all with cowboy boots.

Steph: I wore flat mules with gold detail. For my dress, I visited three shops. The first was Tilted Veil in Guelph. I tried on a stunning dress I had seen on Pinterest, but it just didn’t feel like me. I tried on another dress at a shop in the Distillery, but it didn’t fit the retro mood of the wedding. Then I found a Gatsby-ish floor-length fully beaded dress by Rosa Clara at Kleinfeld. It was perfect. I also bought a beaded purse on Poshmark and earrings from the One of a Kind Show, and I made sheer ruched sleeves with a tassel detail to echo Adam’s fringe.

Adam: Steph did so much herself. She curated playlists, made invitations that looked like vinyl records, and spent two full days making bouquets and building an arch out of chicken wire and fake flowers for the ceremony.

Steph: My friend Katie, a co-owner of the Old York Tavern, helped us pick out wine. Kwento made our heart-shaped vintage cake topped with disco cherries, plus matching cupcakes. Instead of a formal dinner, we hired All the Graze to put together a massive grazing table.

Adam: A friend and talented mixologist, Joe Broadhands, agreed to bartend for us, and he made three signature drinks: one for me, one for Steph and a mocktail for our daughter.

Steph: Finally, our wedding day arrived, on June 22, 2024—the second-longest day of the year. The ceremony, which was held in the property’s intimate courtyard, was casual, with the perfect amount of personal touches. Charity Adams, a minister who offers open-minded ceremonies and calls herself a modern nun, officiated.

Adam: It rained before and after the ceremony but held off during.

Steph: We had spent a long time thinking about our vows, and I planned to write mine down, but in the flurry of the day, we ended up speaking directly from the heart—and we killed it.

Adam: When I finished, our daughter, who sat in the front row wearing a purple ’80s dress that Steph had worn to her own parents’ wedding, reached out to give me a fist bump.

Steph: After the ceremony, our photographer, Nathan Cyprys, took some gorgeous photos of us. Then, at the reception, we grazed and danced.

Adam: Our daughter slept upstairs while everyone hung out, and after our parents took her home, the dance party got going. Our friend David Gillespie deejayed for us, and much later—around 3:30 a.m.—he hosted an impromptu Polaroid photoshoot of the remaining guests. We also had our friend Rocky, a videographer for the Toronto Raptors, in attendance. He shot some amazing footage.

Steph: Instead of a guest book, we had an old dial phone from After the Tone that our guests could leave voice notes on for us. We still haven’t listened to the digital file, but I know my dad left a message right before he left around midnight saying something like “It’s past your bedtime.”

Adam: We crashed in the Darling suite, which Tanya named “the Opium Den.” The only downside of a DIY wedding is cleaning up in the morning, but that was part of the fun, in a way.

Steph: It was one of the best days of our lives. I loved seeing our vision of a casual wedding meets fancy house party come to life. I still feel proud when friends rave about what a great time they had.

Adam: Being married feels mostly the same as before. It doesn’t feel like a shift as much as a continuation and affirmation of the deep love we were already lucky to share.

Steph: My advice to anyone getting married is to have the wedding you want and always make sure you’re the ones having the most fun.

Cheat Sheet

Date: June 22, 2024 Photography: Nathan Cyprys (@nathancyprys) Wedding planner: Stephanie Holmes (@tallestmermaid) Wedding venue: The Darling Mansion Decor: Stephanie Holmes Food: All the Graze Dessert: Kwento Late-night snack: Pizza Badiali DJ: David Gillespie Wedding dress: Rosa Clara (purchased at Kleinfeld)