Elaine Welteroth—the Project Runway judge, New York Times bestselling author, and former editor in chief of Teen Vogue—had just returned from her bachelorette retreat in the Dominican Republic as COVID-19 was beginning to spread in the United States. Right around the same time, her now-husband, musician Jonathan Singletary, had been gearing up for his bachelor party in Mexico. “Almost every day in the lead up, another member of his crew, in order of personal paranoia, dropped out,” Elaine remembers. “Once it was clear that postponing the bachelor party weekend was the only decision to be made, our eyes turned reluctantly toward our wedding date.”
Elaine met Jonathan through church when they were both around 12, growing up in Northern California. (Their moms still sing next to each other in the choir to this day.) There wasn’t a romantic connection until they were reunited as adults in December of 2013 when Jonathan came to interview for jobs in New York City, where Elaine had been living since 2008.
“He reached out to me over Facebook to grab drinks while he was in town,” Elaine says. “I was fresh out of a breakup with nothing better to do than meet up with ‘that guy from church,’ but I expected to be home early.” Drinks turned into dinner, then dessert, then a mutual friend’s party, then karaoke in one of those unexpectedly fun, quintessential New York City nights that keeps getting better and better until it becomes unforgettable. Jonathan landed a job in music tech, and officially made the move to the city a couple of months later in February of 2014. “When my mom came to visit me for her birthday that March, we made a big dinner for her to meet all my friends, and she told me to invite him over,” Elaine says. “He tasted my fried chicken. The rest is history!”
By 2016, they’d been dating for two and a half years, and planned on traveling home to California for Christmas when Jonathan said he’d gotten a last-minute gig and wouldn’t be able to make the trip after all. “I was so bummed because it was the first time our families were going to be celebrating the holidays together,” Elaine remembers. “I grumpily travelled back without him and showed up 2 hours late to our family’s Christmas gathering in Napa. Everyone seemed antsy that I was late, which was weird because I’m always late and they usually eat late anyway.”
After Elaine arrived, everyone was instructed to sit down on the couch to watch a family video. “I whipped out my iPhone to capture it on my IG Stories, naturally,” Elaine says. “I started noticing that, for a family video, there were a lot of baby pictures and footage of me growing up. I started to think maybe they were organizing a 30th birthday video for me as I had just turned 30 on December 10th? At the end of the video a song I recognized came on, ‘Magic’ by Coldplay. This was ‘our song.’ It played over a scene where all I could see were flowers being driven towards my parents’ home, then they were being carried up to their door, and next I saw Jonathan say something to my parents on the screen and my mom starts crying and hugging Jonathan. It all sounds insanely obvious now as I think back on the events, but somehow in the moment, it didn’t click because it was all happening too fast. It really didn’t hit me until Jonathan came strolling into the room where we were all gathered to watch the family video. He was in a full suit, singing along to ‘Magic.’ He got down on one knee and asked me to marry him. I was in complete shock, to the point that I couldn’t even speak. Eventually I managed to say ‘of course.’”
Elaine and Jonathan initially thought about getting married in Turks & Caicos. “It was first on our list because it’s where Jonathan took me for my 30th birthday, but the costs would have been prohibitive for too many of our family members,” Elaine explains. California felt too familiar, but they had trouble feeling connected to any other destination.
Serendipitously, during a trip back to the Bay Area, Jonathan had a conversation with family friends from church who offered the couple their home as a wedding venue. “We visited their private estate with our parents and fell in love—the grounds were absolutely breathtaking, set atop rolling hills with stunning views that transport you to Tuscany!” Elaine says. “Suddenly the idea of coming home for this celebration was the only option that felt right.”
Once they selected the date—5.10.20—they really started to get excited. “There was so much symbolism in this sequence of numbers that only come together once in a lifetime,” Elaine explains. “Also, it fell on a Sunday—the day we met as kids and saw each other every week growing up. But it wasn’t just any Sunday, it would be Mother’s Day!” Their wedding plans became a tribute to their mothers, who not only introduced them through church—“but, to let them tell it, they swear it was their collective prayers that made this marriage happen!” Elaine says. “And now, we would be holding the marriage at the home of someone who witnessed us grow up in that same church together. It all felt divinely orchestrated. So, we leaned into all that meaning and wove it into every aspect of the wedding.”
The creative brief was for it to be “an elevated—literally, by the hills of Mt. Diablo—Sunday-gospel-brunch wedding with elegantly plated soul food and a festive black tie dress code.” The couple envisioned every detail with the help of their wedding planner Mindy Weiss.
When it became clear that their dream wedding wasn’t going to happen due to COVID-19, Elaine and Jonathan both felt overwhelming waves of denial. “But as the reality set in, both of us realized that we actually felt more ‘married’ to our date and to each other than we did to our big, exciting plans,” Elaine says. “There was so much meaning wrapped up into the date we picked. Plus, we had a long engagement—3.5 years!—so the idea of waiting any longer felt painful. More painful than losing out on celebrating our wedding the way we had initially envisioned. I kept seeing messages online that read, ‘Love Cannot Be Cancelled,’ and it really resonated,” Elaine says. “So I woke up one day and walked into Jonathan’s home studio and said, ‘I am marrying you on 5-10-20. It may have to be right here on our stoop. And I might be in sweats. But we are still doing this, come hell or high water.’”
Figuring out the “how” became an exciting challenge. “I think what we learned in our process of pivoting is that the key is to get clear on your ‘why’ and what exactly is most important for your wedding,” Elaine explains. “For us, the priority became saving our date. From there, we could move forward to sort out the how.”
The first step was notifying their guests of their change in plans, as it was very apparent by then that it would no longer be safe for their guests to travel or to be together in the way they had originally planned. In their message, they announced that they were saving their date—literally—with a “virtual quarantine wedding” on their stoop in Brooklyn.
“I woke up one morning with this whole vision of how we could do it—and the excitement of planning began,” Elaine says. “In my mind, I saw the faces of people we love from afar surrounding us on iPhone screens and a small group of our local friends in white lining the sidewalk with gloves and masks on. I envisioned transforming our stoop into an altar glowing with pretty lighting and gorgeous florals. I had no idea if any of this was even possible in the middle of a pandemic, but I was excited about having a new wedding vision to work towards.”
They wanted the stoop to be the centerpiece of their virtual wedding because it’s a space that holds a lot of significance for them as a couple—especially during these quarantined times. “For New Yorkers without rooftop access, a backyard, or a weekend home upstate to escape to, a stoop becomes your coveted slice of outdoor space—your one refuge for fresh air and sunlight,” Elaine explains. “Whenever we need to clear our heads and get out of the house, we sit—or dance—on our stoop together.”
Any time Elaine and Jonathan started feeling a little cabin fever, they would bring a mini speaker out to it and play Frankie, Beverly & Maze’s classic “Happy Feelings,” and dance their worries away. “The neighbors next door and the little kids across the street started coming outside to dance with us from their stoops,” Elaine says. “It brought us all so much joy to smile, and wave, and dance—together, apart—with neighbors who had been merely strangers to us before the quarantine.”
At their wedding, they wanted to recreate that feeling, and spread some joy in the community in a bigger way. “All while maintaining the necessary socially responsible distance, we wanted to give our whole block a reason to dance despite all the devastation in the world around us.”
From there, the wedding became a communal effort. “Whether it was jumping in to DJ or donating a piece from their own closet to help us pull our wedding lewks together, everyone in our tribe contributed something special to the celebration,” Elaine says. “It was humbling to see how our community showed up for us in big and small ways at every step in this process.”
The dress code for guests—both virtual and IRL—was all white. For guests attending via zoom, the couple noted that this was a “waist up” request. During the wedding, one guest commented, “This wedding went from black tie to pants optional. LOL.”
To make the stoop into the centerpiece of the special occasion, Lewis Miller Design installed a whimsical floral arch that framed the front door of the couple’s brownstone. “It was a bountiful explosion of bright, colorful florals that trailed the stair rails,” Elaine says. “It was beyond dreamy and elevated the entire visual experience.”
Notes were distributed to neighbors in advance of the wedding, inviting them to join in the celebration from their stoops, and 200 family and friends joined virtually via zoom. “Additionally, a small group of local loved ones came in person for the ceremony, which observed all of Governor Cuomo’s social distancing guidelines,” Elaine says. “Including maintaining six feet of distance—I even created a social distancing standing chart and wrote guests’ names on the sidewalk in chalk to ensure everyone kept their distance.” They provided gloves and masks on-site in addition to white parasols, bubbles, seeds to plant flowers, and homemade brownies from Elaine’s mom’s family recipe in a gift bag.
“As soon as the music started, neighbors poured out onto the streets, onto their roofs, and some watched from their windows with homemade signs or pots and pans to celebrate with us,” Elaine says. They cheered as the bride walked down her “Soul Train” sidewalk aisle in a label-less white dress from her own closet. “I hadn’t worn it in over three years,” she says. “But it was the first idea that came to mind when I envisioned us getting married on my stoop. And since the mantra we set for our stoop wedding was, ‘do the best you can with what you have,’ I decided to not overthink it. My mom mailed me her wedding dress from California to try on, and I loved it, but didn’t quite feel like me in it. I still wanted a piece of my mom with me that day, though, so I decided to wear her veil. It ended up matching the dress perfectly.”
With so much to do the morning of, Elaine ended up doing her own makeup in the backseat of a car. “I did touch ups perched on the floor in front of a mirror where my longtime friend and ‘hair husband’ Vernon Francois guided me through a live wedding hair tutorial. He was always supposed to do my hair for my wedding—I’m so happy I didn’t have to give that up!”
Close friend Aurora James of Brother Vellies insisted on making Elaine a custom pair of shoes to wear on the day, and they just barely cleared customs in time. “They were the one fancy thing on my body when I walked down the aisle,” the bride says. Meanwhile, Jonathan wore a white vintage blazer he borrowed from a friend, along with white linen pants with a fresh pair of white sneakers.
Officiating via Zoom was Dr. Stanley Long, the founding Pastor of South Bay Community Church, the couple’s home church in California. “He has known both of us and our families for most of our lives so it was very special to have him marry us,” Elaine says. Jonathan took on the role of music director and worked with Rootstock Republic, who helped the couple hire violinist Jannina Norpoth and cellist Malcolm Parson for the ceremony. A label on the sidewalk showed each guest where they were supposed to stand, to ensure distancing, and everyone had a Face-Time buddy so Elaine could see those who couldn’t be in attendance IRL as she walked down the aisle.
After the couple said their vows, the “virtual” block party commenced. “We sent our wedding party playlist to everyone in advance and asked them to join us for our dance party,” Elaine explains. The couple’s friend Adeline Bolden, a Brooklyn-based singer and musician, DJed the wedding as IRL guests danced in the street and on the sidewalk while keeping a distance from one another. “She played everything from Stevie Wonder classics to the Wobble, a cookout hit,” Elaine says. “Everyone let loose and had a blast.”
At one point, an ambulance drove by, and the entire block cheered in unison. “At another point, during our first dance, a police van approached, but when they saw that everyone was wearing masks and maintaining a safe social distance, they passed by without stopping—and the entire block went into an uproar,” Elaine says. “I think we all felt a collective sigh of relief. Then the DJ started our first dance song over, “Find Someone Like You” by Snoh Aalegra, and we got to do it over, the way we planned—this time with all the love and energy of our whole community cheering us on. It was nothing short of magical.”