A Well-Planned Date That Sealed the Deal and Inspired an App

A Well-Planned Date That Sealed the Deal and Inspired an App

The 14 guests who sent screen shots of negative Covid tests to Jordan Scott and Nick Gash before their New Year’s Eve wedding did so out of devotion to a couple whose love felt worth leaving home for amid a pandemic. But they couldn’t have been blamed for expecting to attend a more action-packed celebration than normal.

Ms. Scott, 26, and Mr. Gash, 32, have flown over the Hudson River with their legs dangling out of a helicopter. They’ve taken a couple’s welding class. They’ve visited New York speakeasies, built their own lamp and, since Covid, painted each other in the style of Picasso as part of a virtual art class.

For Ms. Scott, the founder and chief executive of Cobble, an app that curates dates for couples who want to avoid the romantic doldrums, knowing how to generate a good time is a calling card. Mr. Gash, whom she met at a dive bar, gets credit for teaching her how.

Ms. Scott was an underage New York University student in April 2015 when she was introduced to Mr. Gash at the now-closed Exchange Bar & Grill, in the Gramercy neighborhood of Manhattan. “Jordan likes to say it was a dive bar, but to me it was just a very welcoming spot, a neighborhood hangout,” Mr. Gash said.

With the help of her N.Y.U. friend Natasha Van Duser, a bartender, the 20-year-old Ms. Scott slipped past the doorman on a crowded Thursday night. When Ms. Van Duser pointed out Mr. Gash, then an analyst for the personal finance company Bankrate, and introduced him as a regular, she fought an eye roll.

“All I heard was ‘regular,’ and I thought, ‘Um, no,’” she said. “But he put his hand out to shake, which I found strangely professional in a grimy bar, so I shook it.” Then she lost herself, and Mr. Gash, in the crowded bar. “It was one of those nights we yearn for these days, with everyone smooshed together and the music so loud you have to scream to be heard.”

When she bumped into Mr. Gash later that night, the professional vibe was still with him. He told her he flew drones as a hobby and was considering launching a business around them. She mentioned she was interviewing for an internship at Vice the next day. A light bulb went off. “I said I thought drones would be a perfect story to pitch to Vice if they asked me for any ideas,” she said. “Remember, it was 2015 and drones were especially cool.”

She asked him for his number in case she had drone questions before her interview. He took her number instead and told her he would text her in the morning. He never did.

“Needless to say, at my interview Vice asked if I had any story ideas,” she said. “I said, ‘Drones.’ They said, ‘What about them?’ I had absolutely no further information, and therefore never interned at Vice.” She wasn’t mad, though. Later that day, she visited Ms. Van Duser at the bar again. Mr. Gash was there.

“‘You were supposed to text me!’” she said. “’About drones!’” By the time she left, the blown internship was forgotten, its memory chased off by Mr. Gash’s charm. “He was so witty. I had no idea what was going to come out of his mouth next.”

Mr. Gash, 32, grew up in Hauppauge, N.Y., on Long Island, with two sisters, Dayna and Jackie, and his parents, Jeffrey and Cari Gash. He graduated from James Madison University in 2010. “Moving to Manhattan after college was always the plan,” he said. Having a serious girlfriend while he found his footing career-wise wasn’t, really. But when he asked Ms. Scott for a first date a week after they met, he put together an elaborate evening.

“I felt I needed to up my game,” he said. “Right from the beginning I knew Jordan was special and that I had to shake this dive-bar rep.” In one of their shouted conversations at the bar, Ms. Scott had mentioned she had recently seen and loved the movie “Whiplash.”

“It’s all about jazz, so I thought I’d surprise her by taking her to a jazz club,” he said. First he took her to Otto Pizzeria, near Washington Square Park, where they decided to forgo pepperoni and be adventurous. “Neither of us had ever had a clam pie,” Ms. Scott said. “It was the best pizza ever.” A few blocks away, at Zinc Bar, both fell in love with the 10-piece house band. At intermission, they approached a trumpet player to compliment his performance. His response made Ms. Scott melt. “He was like, ‘I wouldn’t have guessed you two knew there was a band onstage, you were so busy looking into each other’s eyes.,’” she said.

Ms. Scott and Mr. Gash both lived with roommates in Gramercy at the time. They had barely said good night to each other when they met for a trip to Central Park the next day. The rendezvous they call their 48-hour first date ended that night with dinner at Pomodoro, an Italian restaurant on the Upper West Side. “It was the best date I had ever had, just so thoughtful,” Ms. Scott said. But if love was dropping anchor, neither was ready to sit still.

“I was going away for a summer abroad with N.Y.U., and I told him I didn’t want to be attached when I was in Italy,” Ms. Scott said. Mr. Gash agreed they shouldn’t get too close. “I told her, yeah, you should be open and free,” he said. Within hours of her flight touching down, though, they were exchanging text messages. When she returned to New York, “that was it. We were officially together,” she said.

Mr. Gash had already met Ms. Scott’s parents, Jeffrey and Lisa Scott, when she took him to their lake house in Averill Park, N.Y., that year on the Fourth of July. Weeks after they started dating, Mr. Scott had invited a group of friends to the foodie-magnet Manhattan restaurant ABC Cocina to celebrate his 48th birthday. He told his daughter the invitation was open only to couples, but she didn’t want to miss out. “I was like, I’ll do whatever I need to do to go to this dinner, so I asked Nick,” she said. “I had just met him and all my dad’s intimidating best friends were there, but he held up so well.”

“Looking back, Jordan was always full of energy for whatever struck her motivation,” Mr. Scott said.

“I’d often come home to her having some sort of lemonade stand, selling stuff in our cul-de-sac. One time she did a bookstore and was charging $100 for used books,” he added with a laugh.

That was in Guilderland, N.Y., where Ms. Scott grew up with an older brother, Dylan. “She would recruit other kids to work for her,” her father said. “There were definitely early signs that she was entrepreneurial.”

When she graduated from N.Y.U. in December 2015, she wasn’t sure where that instinct would lead. Her degree, from the Gallatin School of Individualized Study, was geared toward a career in journalism; she had interned at Cosmopolitan magazine, NY1 and NBC News. But her first real job, as a news associate at “CBS This Morning,” caused her second thoughts. “As much as I loved the show, I realized pretty quickly that I didn’t want anyone else’s job there.” Six months in, just after she and Mr. Gash moved to the West Village together, she quit.

“It was like, ‘Oh, I know we just moved in, but I’m quitting my job and I’m not going to look for a new one,’” she said. Mr. Gash, who was moving up the ladder at Bankrate and is now vice president of partnerships at the real estate tech company Clever, was unconcerned. “I hadn’t envisioned her quitting her job that first month, but I was totally confident she was going to be able to do what she set out to do,” he said.

What she set out to do was launch Cobble, which she envisioned as an extension of sites like Tinder. “Dating apps were becoming super popular at the time, and I was thinking, there needs to be an app for once you find someone and delete the dating app,” she said. “Now you’re growing your relationship. What would an app for me and Nick look like?” First she built a website, idk tonight, that drums up New York date ideas, like “see the city from your own private igloo on a rooftop.” But “I knew there needed to be some extra tech to sort of guide couples through content, to help them make decisions,” she said. That extra tech became Cobble. The app was in development by 2019, the same year Ms. Scott won Entrepreneur Magazine’s Elevator Pitch competition for the concept. “The launch was supposed to be in 2020,” she said. “That’s when the world went crazy.”

If there was a stabilizing force amid the craziness, it was Mr. Gash, who had proposed on Dec. 31, 2018 during a vacation to the Bahamas. On a beach walk, he asked her to stop at a jetty. “He was like, ‘Can you go stand on that rock?’” she said. She thought it was an athletic challenge and climbed to the top. When she looked down, he was on one knee. With his words “Will you marry me?” and hers, “Yes,” those on the beach erupted in cheers.

Planning a wedding eventually became nothing to celebrate, though. Back in New York, in a new apartment on the Upper West Side, they settled on an October 2020 wedding for more than 200 in the Hudson Valley. “We wanted a long engagement, but that came back to bite us in the butt because of coronavirus,” Ms. Scott said. The launch of Cobble wasn’t quite as doomed. In June 2020, after raising $3 million in seed money, its first users signed on. “It turned out to be a great excuse to showcase all the amazing things you can be doing while you’re at home.”

It also set them on a path to envisioning how an intimate, at-home wedding might be made spectacular. A little scouting this winter turned up an Airbnb property in Mount Kisco, N.Y. It was big enough to accommodate both families and a few friends, including the maid of honor Lexi Rabadi, an actor who moonlights as a yoga instructor, and her boyfriend, Matthew Farcher, an actor who was ordained through the Universal Life Church to officiate.

On Dec. 31, Ms. Scott, holding a bouquet and wearing her mother’s wedding dress, walked arm in arm with her parents down the Airbnb’s hallway to a formal living room. Mr. Farcher and Mr. Gash, in a velvet tuxedo jacket and bow tie, awaited her near a candlelit bay of windows, with sofas arranged to face the makeshift altar. “We are observing an outward sign of an inward union that already exists between these two,” Mr. Farcher said. The couple read handwritten vows.

“I promise to provide you with the space you need to grow and shine, without ever being out of reach,” Mr. Gash said.

Ms. Scott reflected on the path she carved to founding Cobble. “For a living I think about decisions and figuring out how to make them,” she said. “Marrying you has been the biggest decision I’ve ever made, and hands down the easiest.”

On This Day

When Dec. 31, 2020

Where An Airbnb property in Mount Kisco, N.Y.

Two Days of Doing The couple and their 14 guests had a two-day celebration, which included a night-before murder-mystery party and a primer on making the traditional Portuguese soup caldo verde with a professional chef. Ms. Scott and Mr. Gash’s mothers both are of Portuguese descent.

Two Weeks Later Ms. Scott said none of their guests, all of whom stayed at the house both nights, have contracted the coronavirus. “Hurrah!” she said.

Something Old Lisa Scott wore the cap sleeved ball gown Ms. Scott was married in for her own wedding in 1990. The pandemic interfered with her buying the dress she planned for the big October ceremony. “That was one happy thing that happened because of Covid,” Ms. Scott said. “I’ve always loved that dress.”

The Finale To ring in 2021, Ms. Scott and Mr. Gash led a group explosion of a pair of confetti cannons.

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