The Worst Boyfriend on the Upper East Side

In the summer of 2018, my friend Julia learned that her mother had a new boyfriend. Julia’s mom, whom I’ll call Rachelle, was a septuagenarian nearing retirement who had been amicably divorced from Julia’s father for nearly three decades. She had signed up for a dating site called Our Time, which catered to an older clientele. (“At last!” the Web site reads. “A dating site that not only understands what it is to be over 50, but also celebrates this exciting chapter of our lives.”) I’d known Julia for more than twenty years—we met during our freshman year of high school—and for that entire time her mom had been single. Though she had casually dated, she’d never found anyone to be serious with, until she met Nelson Roth.

Their first date had been at the Surrey, a luxury hotel on East Seventy-sixth Street, not far from where Rachelle lived on the Upper East Side. She took to Nelson instantly. He was handsome, with a slim build and a full head of hair despite being in his mid-sixties. He started cracking jokes and asking thoughtful questions as soon as they sat down. He was well dressed, in jeans and a crisp white shirt, an outfit suggesting both means and easy confidence. He was in business and, at the moment, in the middle of a major deal. He also told Rachelle that he was an art dealer. She noticed that he wore a showy watch with a red band on his left wrist, which he flashed frequently. This lack of subtlety wasn’t exactly a turn-on, but she found Nelson impressive, charming, and, above all, tremendously fun.

They decided to meet up again, and then again, always at the best restaurants. Nelson would treat, and he tipped well. Everyone around town seemed to know him, and greeted him by name; a doorman at the Carlyle would welcome him in, and the hostess at the hotel bar would usher him to a table. Nelson was boisterous, frequently chatting up strangers. He seemed dazzled by the world—and by Rachelle. She recalled him saying that he could spend all day looking at her. After just a few weeks, they were an item.

Nelson was constantly boasting about his various homes—his apartment in London, his house in Saint-Tropez—although he told Rachelle that his primary residence was in New York, at 35 East Sixty-third Street, a mega-mansion a block and a half from Central Park that had been converted into luxury apartments. He was tiring of the city, however, and he told Rachelle that he felt like settling down somewhere quieter—maybe Connecticut. They talked about looking at homes together. They had been dating for only two months or so, but everything in Nelson’s life seemed to move at warp speed.

Nelson set up a meeting with a high-end New York City broker. Rachelle wondered why they would meet with someone in the city to explore Connecticut real estate, but Nelson insisted that this broker had all the right connections. He also wanted Rachelle to go alone to the meeting. He told her not to mention him, and to make it seem as if she were looking for real estate for herself. She was puzzled, but she followed his instructions.

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One evening, Rachelle found Nelson distraught. He needed to make an important purchase, but his broker was off the grid, and, it being a Friday night, he wouldn’t be able to get the cash from the bank. He needed seven thousand dollars. Rachelle didn’t have the cash on hand, but her daughter happened to. Nelson, overjoyed, told Rachelle that, if she lent him the cash, he’d give her the money back on Monday, plus an extra five hundred dollars.

Julia had just had knee surgery and was in a foul mood. She’d heard her mother talk about Nelson, and had never had a particularly good feeling about him. Now she was outraged that he would ask to borrow money, and was stunned that her mother didn’t see it the same way. But Rachelle insisted, and so, reluctantly, Julia handed over the cash.

On Monday, Julia didn’t get her money back. Nelson kept promising to get it to her. But day after day passed, and still nothing; each day, he had a new explanation. Eventually, he told Rachelle that he was in the hospital for some heart troubles. Julia, smelling a lie, called the hospital, posing as Nelson’s daughter, and was told that he wasn’t currently a patient. Rachelle said that, when she later spoke with Nelson, he explained that of course there had been no record of him—he had been on a V.I.P. floor.

After a month had gone by, Rachelle paid Julia back herself, but this didn’t assuage Julia’s suspicions. Who was this guy, supposedly rich but obviously strapped for cash, who was borrowing large sums of money and trying to get her mother to invest in Connecticut real estate? “Nelson Roth,” Julia said to me, when I was passing through town that fall, “is the fakest fucking name I’ve ever heard.”

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