46288 On the Fifth Try, a First Date to Remember

On the Fifth Try, a First Date to Remember

Wilson Grad Conn wasn’t going to let his dating inexperience become a liability when he started seeing Rachel Lyn Honig in the fall of 2019.

Rookie mistakes, he knew, were unavoidable. But at 55, he felt he had the life skills to get himself up to speed quickly, and that he had met a woman who merited the effort. “When I found Rachel, I knew she was right for me,” he said.

He hadn’t been a believer in love at first sight, but he became one.

Ms. Honig, 51, and Mr. Conn, now 58, were both living in Manhattan when they swiped right in April 2019. That they didn’t meet until October owes itself to an outsize case of the jitters. Mr. Conn, who goes by Grad, had moved to the Upper West Side in 2018 from Seattle, where he had been Microsoft America’s chief marketing officer, in an effort to revive a faltering first marriage.

“That failed spectacularly,” he said. His former wife returned to Seattle shortly after, leaving Mr. Conn, who had been married to her since 1987, untethered in an unfamiliar city.

Most of his waking hours were consumed with a new job as chief experience and marketing officer at the software company Sprinklr. But by spring 2019 he was ready to lay the groundwork for a new social life, too. He and his wife, who have two daughters, Myrna, 28, and Trinity, 25, were legally separated. “We had started thinking about divorce,” he said. “I thought, I should get out there and start meeting people.”

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When he downloaded Tinder, “I wanted to meet someone who was oriented toward a passionate romantic relationship.” He estimated he scrolled through thousands of faces before he matched with Ms. Honig, who became the first and only woman he met online. A more noteworthy statistic: She became only the second woman he had ever kissed.

Ms. Honig is a psychotherapist in private practice in Manhattan. When she met Mr. Conn, she was living in Midtown and managing Amplify Cooperative, a marketing communications consultancy she founded in 2013.

Like Mr. Conn, she had been previously married; she was divorced in 2006 after a five-year marriage. Unlike him, she had no children and knew her way around dating apps. “I tried a lot of them,” she said, including the rare-for-Manhattanites Farmers Only. In her 14 years of post-divorce dating, she estimated that a total number of men she communicated with had surpassed 3,000. Of those, she met hundreds in person.

Mr. Conn’s profile photos on Tinder, including one with his DeLorean, struck her as “kind of zany,” she said. Also, “he had his first and last names on his profile. Nobody does that.” The full name enabled Googling him, though, which helped her piece together a fuller picture of the man who had started messaging her for dates but not following through.

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“I knew his professional background, I knew the company he worked for,” she said. She liked both. If she hadn’t, she wouldn’t have been as patient with his excuses, including one he texted from London hours before they were supposed to meet in New York. “It was like, Come on, buddy. You’re on another continent.”

Mr. Conn canceled four dates with Ms. Honig before he asked his assistant to make sure he attended one they scheduled for Oct. 4. “She literally pushed me into the elevator,” he said. “My legs were so stiff they wouldn’t bend.”

Ms. Honig had invited him to a screening at the Paley Center in New York of a “West Wing” episode followed by a question-and-answer session with Aaron Sorkin, the series creator. She threatened to quit communicating with him if he canceled. “It was worded powerfully,” he said. “It was effective.”

He knew he was in love when they sat down for a drink at the 21 Club before the event. But when they parted company at 1 a.m., the feeling wasn’t mutual. “He didn’t offer to get me an Uber or even walk me to the curb,” she said. Mr. Conn now calls that “a bush league move.” Ms. Honig, who found him earnest and sincere, agreed to a second date anyway.

On that date, 10 days later, she became his second-ever partner for a passionate kiss. At her suggestion, he leaned in on a walk along the East River, “I was shaking like a leaf,” he said. The result generated a mixed review. It was, “strong potential, needs work,” Ms. Honig said. Mr. Conn was eager to put in the hours it took to learn.

By mid-October, though it was a new endeavor for him, Mr. Conn was exhibiting a gift for romance. For a third date, at Bistro Vendôme, a French restaurant in Manhattan, he arrived with a beribboned robin’s egg blue box. Inside was a compass from Tiffany & Company. A note attached said, “Thank you for helping me find my way.”

“Rachel literally instructed me” on how to be a boyfriend, Mr. Conn said. But he didn’t want to remain one for long.

Ms. Honig grew up as an only child in Rockville Centre, N.Y. Her mother, Patricia Honig, a librarian, died of throat cancer in 2002. Her father, Ronald Honig, is the owner of Ron Honig and Company, a floor covering sales agency. In 1993, she earned a bachelor’s degree in art history and ethics from Smith College. Last year she received a master’s degree in clinical mental health counseling from Northwestern University.

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Mr. Conn grew up in Toronto and Vancouver, British Columbia, with a younger brother and sister and graduated from Queen’s University with a bachelor’s degree in marketing in 1985. His mother, Genevieve Conn, is a retired high school French teacher. His father, Charles Conn, an advertising executive, died of pneumonia in April.

When he met his previous wife, in college, “he was smitten and felt he had no reason to look any further,” his mother said. That he felt the same way after a single date with Ms. Honig, she added, doesn’t point to impulsivity or limited patience for playing the field. “Grad is quite deep, and very measured in what he does,” she said. Ms. Honig, however, was a jolt of instant chemistry.

Ms. Honig wasn’t sure it was healthy. In November 2019, she wondered aloud whether, by becoming his girlfriend, she was depriving him of dating experiences he might benefit from. But when she suggested he see other women, it was a hard no. “When you know, you know,” he said.

Six months into their relationship, when Covid started tearing through Manhattan, he suggested they apply for a marriage license in case one of them got the virus. “That was in the days when you thought if your person was hospitalized, you could go sit with them,” Ms. Honig said. “Grad had amazing foresight. He knew we were going to want to be there for each other.”

That license went unused and expired in August 2020. But the sense of rightness both felt on obtaining it never left them. Mr. Conn, whose divorce was final in March 2020, proposed twice. The first, on Sept. 12, 2020, happened on a midnight walk on an island off the coast of Boothbay Harbor, Maine, where Ms. Honig spends summers.

“Grad had carved our initials in the boathouse the way other people do,” Ms. Honig said. “We went and saw that, and then he proposed to me under the stars.”

She said yes a second time when he proposed three weeks later, on the anniversary of their first date, during a visit to Frank Lloyd Wright’s Fallingwater, in Mill Run, Pa. The trip was to celebrate their mutual love of midcentury-modern design.

The grand wedding for 325 they put on at the TWA Hotel at JFK Airport in Queens on Dec. 10 was also a tribute to midcentury modernism, but the date had been chosen for another mutual passion: Christmas.

“Grad has been known to count down Christmas as early as January,” Ms. Honig said. The couple now split their time between Ms. Honig’s apartment in Midtown; a house in Delray Beach, Fla., they bought together in 2020 to be closer to Ms. Honig’s father; a cottage on Long Island Ms. Honig’s mother left her; and Mr. Conn’s work residence in Houston. In May 2020, he left Sprinklr to become chief marketing officer at PROS, a software company based in Texas.

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Both like the idea of eventually dedicating a yet-to-be-purchased house to Christmas exclusively, with a tree up and carols playing year-round.

At the wedding ceremony, guests got a glimpse of how that might look. Dozens of Christmas trees done up in tinsel and ornaments the couple asked their friends and families to bring in lieu of gifts dotted the capacious onetime air terminal. Scenery also included a Christmas-themed ice sculpture and Grinch-inspired wedding cake. “The place was transformed into an absolute wonderland,” Ms. Conn said.

Ms. Honig, wearing a pillbox hat and a custom Anne Barge wedding gown with a jeweled belt, walked with her father down a candlelit staircase. Mr. Conn and his mother descended a staircase on the opposite side while he was dressed in a tuxedo by Tom Ford with a shawl collar. Ms. Honig’s cousin, Marian R. Shelton, a retired judge of the New York State Family Court, met them at an altar strung with festive greenery to officiate.

In handwritten vows, Ms. Honig called Mr. Conn “a unicorn among men.” Mr. Conn thanked Ms. Honig for helping him believe in love at first sight. After both repeated “with this ring I thee wed,” the proceedings took a break from Christmas when Mr. Conn stomped a glass, a nod to Ms. Honig’s Catholic-Jewish upbringing.

With a cheer of “mazel tov!” from the crowd and sleigh bells ringing in the distance, the couple recessed through the terminal, hand in hand.

When Dec. 10, 2022

Where The TWA Hotel, John F. Kennedy Airport

The Most Wonderful Time Ms. Honig’s wedding prep included a Christmas-themed Mani-Pedi. “Every bride should have snowflakes on her nails and candy cane toes,” she said. Her jewels for the ceremony featured her late mother’s opera-length pearls; Mr. Conn wore vintage TWA port of call cuff links, a gift from the bride.

Traditions Food stations at a reception in the terminal reflected both sides of Ms. Honig’s background. One offered a Christmas turkey dinner with all the trimmings, the other, Chinese food.

Unbroken The couple hired predominantly woman-owned wedding vendors. One, the Israeli artist Talia C., made the glass Mr. Conn broke underfoot. After the wedding, the shards were collected. The artist will repurpose them into resin candlesticks for the bride and groom’s table.

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