A Festive Florida Wedding With Two Cocktail Hours, Two Aisles, Two Rabbis, and Two Receptions
In August 2018, Madeleine Gerrick ventured on her first-ever Bumble date with LGBTQ+ mentor and documentary executive producer J Winkelried at the bar Lovers of Today in the East Village of New York City. “We spent the first night we ever met drinking cocktails in the corner booth singing oldies together,” says J.
Three-and-a-half years later, J planned a proposal that would lead them back to that pivotal spot in their romantic history. “I told Maddie that we were meeting friends downtown to carpool to a museum event together to Connecticut. But when we were walking by Tompkins Square Park to meet everyone, I said I wanted to quickly pop in,” they share. “We walked into the bar to ‘Wouldn’t It Be Nice’ by The Beach Boys and there was a Lite Brite—something Maddie always wanted as a kid—that said ‘Marry Me?’ on the bar counter. I even looked up the menu ahead of time and asked the bartender to have the cocktails we drank that first night there waiting for us. I was such a nervous wreck that I left my glasses in the Uber we took there!”
Even though there was already a proposal, Maddie wanted J to experience that incredible surprise, too. She organized a huge group of their friends to attend a Yankees game together and had the words “J, let’s cheer on the Yankees together forever, marry me?” displayed on the Jumbotron. J shares, “I kept saying, ‘I can’t believe we got 20 of our friends to come to a Thursday night baseball game!’ Little did I know… If I had, I would have worn something nicer than my ‘George Costanza’ Yankees jersey. I love that being queer allows us to both experience the magic of a proposal. We think everyone should have that!”
When the to-be-weds began brainstorming their wedding vision, they first thought that as a queer couple, New York City would be the perfect location. “It’s our forever home and where we feel safest and happiest,” says J. “But we also knew we wanted a different type of wedding—one that was outdoors and at a venue that would allow us to customize our guests’ experiences outside of the traditional ‘ceremony-dinner-dancing’ party we often see.” When J’s parents offered up their family home in Florida to serve as the venue, the couple realized the beautiful property, which held so much meaning for the two of them, was the right fit. “At our intimate shabbat dinner the first night, our friends’ toast summed it up perfectly: ‘Welcome to Florida: the ultimate gay wedding destination!’ Even in a state where it is illegal to say the word gay [in schools], we knew it was important to celebrate ourselves and our love there because love will always win.”
Maddie and J worked with planner Marcy Blum to execute their wedding weekend experience. “We wanted our wedding to be fun, bright, entertaining yet relaxing, and offer more experiences than just dinner and dancing,” they explain. The celebrations began with the outdoor shabbat dinner on Friday night, followed by a “Palm Beach chic” welcome party at The Colony Hotel the next day.
The wedding day itself broke from traditional form, with plenty of key elements coming in pairs. The day began with the couple signing their ketubah with a small group, then joining the rest of their guests for a pre-wedding drink. “Everyone knows cocktail hour at weddings is sometimes the best part, so we thought, ‘Let’s have two!’ The pre-ceremony cocktail hour overlooked the beach, where the giant deck for the ceremony was,” share the couple.
For this first part of the day, J wore a white denim style by 21st Century Kilts, a Zegna tuxedo shirt, Celine canvas combat boots, and a Fry Powers silver studded pearl necklace. Maddie donned a rose corset top and oversize tuxedo pants by Danielle Frankel and Manolo Blahnik pearl heels. “Being able to wear such different types of outfits on my wedding day allowed me to express myself and my love for fashion,” says J. “We wanted to have fun by playing with her wearing pants while I wore a kilt.”
After the first cocktail hour, Maddie changed into a Chanel ruched strapless top and lace skirt with Maria Tash diamond stud earrings. “She loved how the very feminine lace skirt was offset by the edgy top and punk earrings—a perfect summary of her style all in one,” says J. “Being non-binary, I’ve always had challenges finding formal clothes that don’t make me feel like I’m in a costume. A few years ago, I came across the designer Emily Bode. I got a few pieces of hers and from the second I put them on, I had never felt so affirmed in my gender identity, which is something I’ve never experienced but had always been searching for.” They wore custom Bode shorts and a shacket made out of an unused army infirmary blanket to exchange vows.
The ceremony deck, which was built over the sand, featured a blue ombré seating arrangement that split to allow for two aisles. “Being a queer couple and J being trans-masculine non-binary, there was no ‘bride’ or ‘groom’ at the wedding, so we didn’t want our ceremony to have any gendered traditions,” the couple explains. “We walked down together before meeting our respective parents, who walked us down the two aisles at the same time before meeting again at the chuppah.” As an extra special touch, the couple had musician Calum Scott sing “Biblical” throughout their procession.
“My two rabbis that I have known most of my life—one of which supported Maddie throughout her entire conversion to Judaism—were there under the chuppah to marry us,” says J. “Our rabbis used multi-gendered Hebrew throughout the ceremony—a very new practice for the evolving queer Jewish community. After we both stepped on glasses, Calum Scott sang his song ‘You Are the Reason’ as we walked back down the aisles and left our guests to experience the performance.” Next came the second cocktail hour, which felt truly unique due to a special activity. “Marcy’s team had the idea to turn our backyard into a putt-putt course—a thrill for all of our guests,” the couple says. Each hole was themed based on a meaningful part of the duo's lives and had three different stations for golf equipment, concessions, and lemonade.
After hosting two cocktail hours, J and Maddie naturally wanted to create two different vibes for their reception as well. The dinner and speeches were held in a large glass tent filled with stunning modern interiors that felt far from the traditional wedding layout. The environment was decorated with soft white couches, seating areas with bookshelves, glass tables, and even a rug-inspired dance floor. “The hanging lamps and huge plants everywhere made it unlike anything we’ve ever felt,” the couple says. “It only brought us and our guests closer together.” Guests enjoyed a tasting menu and “carb carts,” and later watched the couple cut into an exact replica of Elvis and Priscilla Presley’s wedding cake. “We never wanted a typical first dance, because we always prefer to dance with our friends right there with us. So the first time we got on the dance floor that night was actually for the hora,” they share. “It was magic.”
The chic, minimalist tones of the dinner were a stark contrast from the bold colors and energy of reception number two. “We had an amazing jazz club-style tent built in the courtyard of the property, where guests were greeted with passed desserts, wedding cake, and espresso martinis, and one of our favorite bands, Postmodern Jukebox, performed pop hits in their 1950s style,” the couple explain. The space featured a velvet-swathed doorway, printed wallpaper with jungle cats on the staircases, and colorful lanterns above. “There was a vintage Zoltar fortune teller machine and fire-breathing bartenders. Needless to say, our guests are still talking about it.”
After the night of excitement, the newlyweds headed off to St. Barth’s. “We knew we wanted a relaxing honeymoon with great food and where we could feel safe being queer, so St Barth’s really stood out to us,” says J. “Plus, it was where my parents, who just celebrated their 37th wedding anniversary, went on their honeymoon. So, we knew it had good ju-ju. It was absolutely perfect.”
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Photo: Allan Zepeda1/79In mid-February, we welcomed our friends and family to Florida for one long, joyful weekend celebration.
Photo: Allan Zepeda2/79We hosted an outdoor dinner at one of our favorite local restaurants to kick off our beautiful wedding festivities.
Photo: Allan Zepeda3/79Starting the weekend off with an intimate shabbat dinner was a no-brainer. Friday night set the tone of celebration, love, and family for the entire wedding weekend.
Photo: Allan Zepeda4/79Marcy Blum and her team arranged a gorgeous coastal tablescape to compliment our family-style dinner.
Photo: Allan Zepeda5/79All smiles on night one!
