On a humid July night, Madeleine Kelley and Amar Singh shared a bottle of orange wine on their first date in Brooklyn. Just four years later, the couple would toast again as newlyweds in California wine country. The pair first connected when Amar, a product manager at Google, was visiting the city from Los Angeles. “I had decided to spend six weeks in New York in the summer of 2021, which is when I met Madeleine at Have & Meyer in Williamsburg,” he says.
Clearly, that first date went well. “After just a couple of weeks, we started dating long-distance, traveling between LA, where Amar lived, and the East Coast,” says Madeleine, who works in documentary film. “At the time, it seemed natural and was such an adventure together. After a year-and-a-half or so of being on the move, we decided to build a life together in Brooklyn.”
Amar would hop on one more plane ride to see Madeleine to ask a very special question. He was at a wedding in Canada but then made a trip to Rome, where Madeleine was visiting friends. “It would require a five-hour drive and three flights, but it seemed like the best opportunity for a legitimate surprise,” says Amar.
Madeleine had no idea he was on the continent when she went with a friend to Hotel de la Ville for a rooftop drink. A concierge was supposed to escort them to the bar but instead led them to a hotel suite. “Before I had time to think, the concierge quickly ushered me out onto the terrace, and there was Amar, in a suit, holding a ring—definitely not in Canada!” she recalls. “I was completely shocked. After the proposal, we had a private dinner in the suite then went out all evening and celebrated with friends at the Soho House rooftop. I thought we’d be flying home the next morning, but Amar had already arranged with my job for us to stay longer and booked us a few extra days in Rome. It was such a deeply romantic city to get to celebrate our engagement in.”
Deciding to tie the knot at Madeleine’s family home in Calistoga, California, was an easy choice for the couple. “I like to joke that Madeleine had a date and venue ready 15 minutes after I proposed,” says Amar. The celebrations would take place over the weekend of June 14, including a sangeet at Estate Yountville and a rehearsal dinner at The Charter Oak in St. Helena (which happened to be the same location, then called Tre Vigne, as Madeleine’s parents’ rehearsal dinner 33 years earlier). The pair also decided to work with Shannon Leahy Events, which planned the bride’s sister’s wedding the previous year. “Shannon has a unique ability to be both a creative force and a grounding presence,” says Madeleine. “Her team can dream up the fantastical while making the process feel genuinely easy and fun. They brought not only extraordinary vision to the process but also a spirit of collaboration, curiosity, and joy, which was very important to us.”
Dining and Cooking