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 L.A., where Amar lived, and the East Coast. At the time, it seemed natural, and was such an adventure together,” says Madeleine, who works in documentary film. “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 made a trip after 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 her friend Max to Hotel de la Ville for a rooftop drink. A concierge was supposed to escort them to the bar, yet led them to a hotel suite instead. “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! I was completely shocked,” she recalls. “After the proposal, we had a private dinner in the suite, then went out all evening and celebrated with friends at the Soho Hotel 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 The Estate Yountville and a rehearsal dinner at The Charter Oak in St. Helena. “The same location (then called Tre Vigne) as my parents’ rehearsal dinner 33 years earlier,” says Madeleine. The pair also decided to work with Shannon Leahy Events, who 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–her team can dream up the fantastical while making the process feel genuinely easeful and fun,” says Madeleine. “They brought not only extraordinary vision to the process, but also a spirit of collaboration, curiosity, and joy, which was very important to us.”