The Bride Wore Vintage ’90s Valentino and Her Grandmother’s Bracelet for Her Beachside Wedding in Mexico

Sarah Istel and David Shay’s first date almost didn’t happen. It was February 2025, and David had messaged Sarah four times to get her to say yes to drinks at the Ugly Duckling, a now-closed bar in Washington, D.C. “I did not love dating,” Sarah explains.

She even called her mom on the way to the date, asking if it would be rude to cancel at such short notice. Sarah’s mom told her she had a good feeling, but that she would call during the date with a “fake emergency just in case.” The date ended up lasting four hours. “I remember being captivated by Sarah’s energy and smile,” David shares. “The conversation seemed to just come easy.” They laughed a lot, and the time “flew by,” David says. Suffice it to say, Sarah did not need the escape route. After the date, she called her mom to tell her she was glad she went.

They continued seeing each other, and David gave Sarah faith in their compatibility. “Very early on in our relationship, in a moment of rare vulnerability for me, I told David that I am not good at being happy in a relationship,” Sarah says. “It just sort of slipped out, and I immediately felt embarrassed. But he took my hand without hesitation and said, ‘Don’t worry, I’ll teach you.’ He has lived up to that promise.”

In November 2025, David proposed to Sarah. He planned a surprise weekend getaway to Charlottesville, telling her he had a padel tournament there. At the time, she had just started a new job as a managing director at a venture capital firm focusing on energy investments, after spending years in government service, including as Deputy General Counsel for the Intelligence Committee. When David insisted she skip a work meeting to leave early on Friday with him, she was confused by his uncharacteristic sternness. When a notification popped up on the car ride that said “David’s proposal—photographer,” she pretended not to see. He proposed by a lake at a vineyard, and she said yes.

They then went to one of their favorite hotels and toasted with Champagne. When they got home to D.C., David had yet another surprise waiting: 100 of their friends at Maxwell, their local wine bar, to celebrate their engagement. “The best part was that he had gotten Mount Dessert, our favorite ice cream place, to make a gallon of ‘the dude flavor’ for the occasion,” Sarah says, adding: “They only make it one month a year, so I savored that gallon for a while.”

They decided to have essentially three weddings: “A big party in D.C. for everyone we love on April 18, a small ceremony at my dad’s beach house where I grew up on May 1, and our wedding in Los Cabos,” Sarah says.

For their main wedding location, they wanted somewhere “with an easy flight, on the ocean, that would feel like a vacation for friends and family,” Sarah explains. Los Cabos fit the bill, and they went with the Four Seasons Costa Palmas. They worked with wedding planners Lee de Lange and Adilenne Rodríguez to pull off a weekend of disco, tacos, beach partying, and more.