Dancing in the Street: Elaine Welteroth Got Married on Her Brooklyn Stoop, Then Threw a Virtual Block Party
Elaine Welteroth—the New York Times best-selling author, Project Runway judge, 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 and 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 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 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 traveled back without him and showed up two 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 and 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—May 10, 2020—they really started to get excited. “There was so much symbolism in this sequence of numbers [5-10-20] 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 Mount 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 Canceled,’ 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.”
