Real Weddings: Josh and Jenna

Jenna Cynamon, a 30-year-old head of marketing at a skin care company, first met Josh Rubin, a 32-year-old head of sales at a tech company, at a downtown Toronto after-party in 2016. They began dating a few months later and made their relationship official in early 2017. But it wasn’t until 2022 that Josh proposed to Jenna on Malibu Beach. Their destination wedding gathered 80 guests at a luxury resort in Palm Springs for a mid-century-modern-themed celebration. Here’s how it all came together.

Jenna: I first met Josh in the summer of 2016. I was out at a club—Spice Route on King West—with my friend Maddy. The guy she was dating at the time, Jordan, was having people over at his place, near the TIFF Lightbox, for an after-party. I expected it to be a big group of people, but when we arrived, it was just Jordan and his friend Josh.

Josh: My memory of first meeting Jenna is a little blurry since it was 3 a.m. But I remember having a great conversation with her. Jenna was really funny, and we got along well right off the bat. There was definitely a physical attraction there too.

Jenna: I also thought Josh was cute. We kept running into each other at clubs and bars on King West that summer. In October, Josh invited me to a birthday party he was going to at Nana, a Thai restaurant on King Street. We ended up going home together that night. It was after the party that Josh asked me out on a proper first date, to Locals Only.

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Josh: We talked a lot about where we’re from—I grew up in Toronto, and Jenna is from Calgary—and our childhoods. We discovered we’re both only children. And we talked about our mutual friends, since we had a lot of them. Also the fact that we’re both part of Jewish communities.

Jenna: We went on more dates after that. We’d go out for dinner a lot since Josh was in the hospitality industry and wanted to check out new restaurants. And we went to the Christmas Market in the Distillery District. In January of 2017, Josh and I made our relationship official. At the time, I lived alone in an apartment in Yorkville, just south of Bloor.

Josh: I was actually sharing an apartment with my cousin, also in Yorkville. When I moved in, he’d joked that neither of us was supposed to get into a relationship while we were living together. He wanted us to enjoy being single bachelors together. Sure enough, a couple of months later, Jenna was in the picture.

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Jenna: In 2018, Josh and I moved into our first apartment together, right next door to his place in Yorkville. He was able to move his stuff right through the shared garage between the buildings.

Josh: When Covid hit, Jenna went back home to Calgary for four months to spend time with her mom. I was sad that she was gone, but I knew that it was important for her to keep her mom company.

Jenna: Being apart was actually incredible for our relationship. We were so on top of each other in our small apartment that some time apart felt like a reset. It made us appreciate the little things more and reminded us that we truly wanted to be together. While I was away, I helped my mom sell our childhood home and relocated her and our 14-year-old dog to a new place in Toronto. Josh was super supportive through all of that.

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Josh: Jenna and I also decided to upgrade to a bigger apartment. She was still in Calgary while I was viewing places, so we did the walk-throughs over FaceTime. She put a lot of trust in me to find us a good spot. We moved into our new place in August of 2020. It was a two-bed-plus-den, two-bath apartment, which gave us a lot more space.

Jenna: Josh and I talked about marriage and kids pretty early in our relationship. It was something that we both wanted. But we got together when we were still young—I was 22 and Josh was 24—so we weren’t in a rush at first.

Josh: As more of our friends were getting engaged and then married, we started to look at each other and think, Maybe it’s time for us.

Jenna: In the fall of 2021, I sent Josh designs for the ring I wanted: a vintage-looking cushion-cut diamond. I told him that I wanted to be engaged by the first quarter of 2022. It felt like the time was right for us to take the next step in our lives.

Josh: Jenna has a family friend in Calgary who is a jeweller, so I got in touch with him and we went back and forth over designs and finding the right diamond. Jenna and I had plans to go to LA in January and stay for a few months, but the ring wasn’t finished until after we left, so I had it shipped from Calgary to LA.

Jenna: My friend Ethan owns a clothing company in LA, Every Other Thursday. In mid-January, he asked me to model for one of his photo shoots on Malibu Beach. I was super excited about it and asked Josh to drive me there.

Josh: Little did Jenna know that I’d asked Ethan to send her those texts. I planned the proposal to happen at sunset, but once we arrived, there were tons of people around.

Jenna: I was about to get out of the car to find Ethan when Josh stopped me and said, “Unfortunately, Ethan’s not going to make it.” I was confused.

Josh: Because the beach was so busy, I decided last-minute to pop the question in the car. I just pulled out the ring and asked her if she’d marry me.

Jenna: I would have hated everyone on the beach watching us, so I’m glad Josh did it in private. He had a blanket and champagne in the trunk, so after I said yes, we sat on the beach and watched the rest of the sunset. I wasn’t totally surprised—I knew we were going to get engaged at some point. But I didn’t think he’d be able to get the ring to LA, so I had it in my mind that he was going to propose in March or April, after we were back in Toronto.

Josh: We dragged our feet on wedding planning for quite a long time. We enjoyed our engagement.

Jenna: We knew we wanted to do a destination wedding. We thought about Mexico, but a lot of our friends had already gotten married there. We also wanted a place that had direct flights from Toronto. It wasn’t until October of 2023 that we decided on Palm Springs. Earlier that year, while we were in LA, we’d booked a weekend trip at the Parker, a luxury hotel, and loved it. The property was so gorgeous, and it had so much character. We looked up the best weather in Palm Springs, and March was the month. The Parker only had dates left in 2025, so that’s how we picked our date.

Josh: The cool thing about the Parker is that it’s a 13-acre property with all these different lawns and areas, so we could use multiple spaces for our wedding. We’d get married on one of the lawns, then do cocktail hour on another lawn with a different view, then have dinner on a third lawn and go indoors for the after-party. We had about 80 guests in total. Most of them booked rooms at the Parker, but a few people got together and Airbnb’d homes nearby. Our guests would arrive on a Thursday, the day before the wedding, for a welcome party, then leave on Sunday.

Jenna: I spearheaded the vision and design of the wedding along with my planners. I chose a mid-century modern vibe and carried it into our choice of plates, furniture and floral arrangements. Yellow stood out as a colour since the Parker has some gorgeous yellow sun umbrellas and a cute lemonade stand. Yellow was also having a moment in fashion. We had a lot of the colour in our florals too.

Josh: It was important for us to have Jewish tradition incorporated into our wedding. We brought our rabbi to Palm Springs from Toronto. He’d actually given Jenna’s grandfather a bar mitzvah at 83 years old, since her grandfather was a Holocaust survivor and hadn’t gotten to have one. Two of our best friends would sign the ketubah, a Jewish marriage licence, before the ceremony. One of them was my friend Jordan, who had introduced me to Jenna in the first place.

Jenna: We also did a floating chuppah with a lot of yellow florals. Josh and I had spent our winters in LA in the few years leading up to the wedding, so it was easy for us to plan things while we were there.

Josh: Shopping for my wedding suit was pretty simple: I just went to Harry Rosen and got a tux. I had worn black tuxes for a lot of my friends’ weddings, so I decided on dark navy instead.

Jenna: I wanted a vintage dress for the welcome party. Initially I chose a floral Dior dress, but it was just not the right vibe: too English garden party, not enough retro Palm Springs. So, at the last minute, I found a Jacquemus polka dot dress online. I wouldn’t have enough time to get it delivered to LA and altered before the wedding, so I sent it to my mom in Toronto, who got it altered on herself since we’re the same size. She flew it down to Palm Springs with her on the same day as the welcome party. For my wedding dress, I saw a Vivienne Westwood design online from her 2023 collection. Before I even tried it on, I knew it was going to be my dress. Bows are having a major moment, and I loved how it felt classic and timely all at once. I got mine from Loho Bridal in LA.

Josh: We had our welcome party at Seymour’s, a speakeasy inside a steak restaurant in Palm Springs. The party was supposed to end at 9 p.m., but everyone was having such a great time that we extended it to 11 p.m. Then some of our friends who were staying in an Airbnb house had a big after-party. That probably wasn’t the best idea: Jenna and I were up until 4 a.m. the night before our wedding.

Jenna: I had to be up at 7 a.m. to start hair and makeup, which was hard. But I powered through. My bridesmaids trickled in around 8 and 9 a.m.

Josh: Jenna and I were staying in a villa at the Parker, but the plan was that I’d get kicked out when Jenna started getting ready. I had planned to meet Jenna’s uncle and cousins to play padel—a racquet sport similar to tennis—at 7 a.m. Afterward, I took a bunch of guys from our families out to breakfast. Then I kicked my parents out of their room at the Parker and got ready there with my cousin, who was my best man.

Jenna: For the ceremony, we had a guitarist and violinist playing instrumental versions of songs we loved. Josh walked in to “Starting Over” by Chris Stapleton, and I chose “Invisible String” by Taylor Swift. The ceremony was about 30 minutes long.

Josh: We had champagne waiting for our guests when they came into the ceremony to help set the tone. Before the wedding, our rabbi had told us to remember to be present and take the moment in, to look around and see our friends and family.

Jenna: I felt a little nervous, but I had my late dog’s tags on my bouquet, and holding on to them calmed me down. After the ceremony, we had cocktail hour on an adjacent lawn with beautiful views of the mountains. We wanted everything to feel elevated and chic with a retro spin, so we served lobsters and caviar, which felt very 1960s. It was important to us to do something different from all the other weddings we’d been to.

Josh: Jenna runs events for her job, so she’s extremely detail-oriented. From sourcing vintage vases and silver trays to custom artwork on the menus, nothing was overlooked.

Jenna: Dinner was in another courtyard. We wanted it to feel super intimate, so we did three long tables. The Parker prides itself on its white-glove dinner service, so everyone at the table was served at the exact same time, in unison. I wanted it to feel like an elevated 1960s dinner party, and I think our guests got that memo. Everyone was table-hopping, running to the bar, and mixing and mingling with each other.

Josh: The food was delicious. We had steak, chicken madeira—one of my favourite dishes—and butternut squash risotto. A retro ’60s band performed at dinner.

Jenna: I wanted the after-party to have a very different vibe, like a swanky retro speakeasy. We had the room draped with red velvet, and there was black furniture, disco balls and a mirrored bar. There was a merch table with fun things for our guests, which I designed and produced myself. There were joints, custom-designed hats, tote bags, matchboxes, keychains and ashtrays. I changed into sequinned pyjamas for the after-party.

Josh: We did the hora during the after-party. Jenna almost got dropped when she was thrown in the air. There was also a vintage photo booth. We partied until 1 a.m. at the hotel, then we went back to our friends’ Airbnb and had an after-after-party until 5 a.m.

Jenna: Our wedding was so much fun. It was just the best time.

Josh: We wanted our wedding to be a fun party, and it was. I was tired at the end of the night, but honestly, I think everything went perfectly. People partied and showed up for us. Everyone was all in.

Jenna: The next day, we had a little pool party at the hotel with all our guests. Then we had a mini-moon in Cabo for a week. We did our official honeymoon in Mykonos and Crete in July.

Josh: Married life has been nice so far. We’d been together for so long that it wasn’t a drastic change in terms of our day-to-day. It’s been nothing but good things.

Jenna: Things are the same, but it’s a little bit sweeter. It didn’t change the fundamental core values of our relationship. It’s been nice seeing Josh wear a ring.

Cheat Sheet

Date: March 27, 2025 Photography and videography: 515 Photo Co. Planner: Duet Events Venue: Parker Palm Springs Officiant: Rabbi Aaron Flanzraich Florals: Luna Design Studios Additional decor: Theoni Collection, Adore Folklore Food: Parker Palm Springs DJ and entertainment: Dart Collective Guest favours: Hats, tote bags, match boxes, keychains, ashtrays and custom fortune cookies designed by Jenna via her business, Off the Aisle; stationery designed by MaddieolaMade. Photo booth: Photomatica Bride’s dress: Vivienne Westwood, from Loho Bride Bride’s shoes: Manolo Blahnik Makeup: Shadi Malek Hair: Robyn Tornabeni Groom’s outfit: Zegna, from Harry Rosen