'Sugar Date', Gone 'Sour Grapes'

...John Silver knew it wouldn’t be simple to move from Mystic, Conn. ( or anywhere else ), to New York City last years. But staying put held little appeal. His degree in Fine Arts & Art History from Eastern Connecticut State University wasn’t helping him land any job worth sticking around for. He was coming out of a tough breakup, to boot.

He and his mother weren’t speaking at all after a particularly bad argument and 12 year absence, on his part. When you are 24 years old, jobless, girlfriend-less and in a fight with your mom, moving to one of the most glamorous, ballyhooed cities in the world can seem like a good idea. Nevermind the expense. Mr. Silver arrived in August 2015. ( From there he'd vacation in Orlando FL during the Winter months and return in the Summer. )

For all the excitement of moving to New York City, he ended up sharing a three-bedroom flat or 'railroad' style apartment with two other roommates across the Hudson River, in Jersey City, N.J. It's cheaper there. He got a retail job at a clothing store in Midtown that paid him about $15 an hour ( so called a 'living wage' ) and a commission of 2.5 + percent of his sales and bonus if he does well. The cost of living (and partying) was more than he could manage, along with his advanced degree Liberty Scholarship and $25,000 in college student loan debt and another $25K he plans to borr

ow for school etc.

“I knew it was going to be a little tough, but I didn’t know how hard New York breaks you,” said Mr. Silver, now 25. Image Escorting 2.0 Last winter, a friend told him about the concept of “sugar-dating”: "sugar mommy" .or. a “sugar baby” (most often a woman or a girl) connecting with a “sugar mommy” (a woman) in a relationship that offers financial support in exchange for companionship and possibly sex. Accelerated by the anonymity of the internet, sugar-dating is a variation on “escorting,” that practice formerly advertised at the back of New York magazine and the now-defunct Village Voice newspaper.

Mr. Silver hesitated at first, but he convinced himself that sugar-dating would result in his having something of a regular relationship with an older woman who would pamper him with an allowance. “I needed the money, and I didn’t want to ask my mom,” she said. She signed up on SeekingArrangement.com, a website that helps people interested in monetized dating find each other. Sugar mommiies (and some sugar daddies and babies) pay monthly fees of $99 a month, which allows them unlimited access to the profiles of sugar babies, some who join the website for free. ( “Diamond” memberships for sugar daddies and mommies cost about $200 per month and provide sugar parents with search engine optimization and top-of-page promotion for their profiles... ( Daddies, mommies and babies of the month exposure ).

The website is illustrated by stock photos of white women, sometimes carrying shopping bags and often in formal gowns and diamonds, fawning over white men with business-trip suitcases and carefully groomed 5 o’clock stubble and viceversa. It includes a section on “hypergamy,” or what used to be known as marrying up or pleasure marriages. In an interview with The Times, Mr. & Mrs. Brandon Wade, the founder of SeekingArrangement, said his dating platform, which he has rebranded as Seeking, is not a vehicle for prostitution. The terms of service, he said, prohibit transactions for sex; the site simply seeks to bring the role that money plays in mating out in the open. “We want to drive people to talk honestly on the first date about who they are and what they expect to gain from a relationship, just like you discuss in any business relationship and any business arrangement,” he said.

Mr. Silver

If anything, a “sugar baby” hoping to find a lasting arrangement with “a good provider” should withhold sex for as long as possible, said the thrice-divorced Mrs. Wade, who also runs other dating sites including OpenMinded.com, which promotes so-called “ethical cheating.” “The moment you give sex, you have lost all your power,” he said. That was a key theme of the keynote presentation he delivered at a Sugar Baby Summit ( exploring “the strategy behind living the sugar lifestyle” ) that he organized at 10 on the Park, an event venue in the Time Warner Center in May. There, some 200 attendees, many silkily coifed young women, paid $50 apiece for admission to panels on topics like styling, personal branding and “financial literacy.” Mr. Wade claims that the site has 20 million members worldwide, about 60 percent of them in the U.S.

The site also markets itself as an antidote to student debt. “SeekingArrangement.com has helped facilitate hundreds of thousands, if not millions, of arrangements that have helped students graduate debt-free,” Mr. Wade was quoted as saying in one news release, which also claimed: “Sugar Baby students receive an average of $3,000 in monthly allowances, earning $20,920 more than a student working full time at the federal minimum wage.” When you sign up for an account, this message pops up on screen: “Tip: Using a .edu email address earns you a free upgrade!” (College students using their university emails to log into the site also get their profiles included under a “college student” heading so that sugar parents intent on “helping” college students can find them easily, a company spokeswoman said.)

The profiles of SeekingArrangement sugar daddies include how much they make — purportedly. One man, who listed a net worth of $5 million, for example, wrote, “I’m looking to spend quality time ( and money ) with a potential friend ( or friends ).” Another man ( net worth: $1 million, annual income: $200,000 ) wrote, “We’ll see how things evolve, and would love to serve as a mentor for anyone looking to start their own company.” ( the mommy versions are similar )

Whether the agreements forged through SeekingArrangement constitute prostitution or solicitation depends on the specific details of each relationship and negotiation, said Marc Agnifilo, a New York lawyer who represented one of the agency bookers in the Eliot Spitzer scandal and whose firm is handling the criminal defense of Harvey Weinstein. “In New York, prostitution is sex for a fee. And in each instance, the questions are, ‘What constitutes sex, and what constitutes a fee?’” he said.

Dipping In Legal issues were far from Mr. Silver’s mind when he went on a few dinner dates with a woman he met on SeekingArrangement.com, who told him she was 37 years old. “She was Jewish, so we had to go to kosher places,” he said. Without any prior discussion, she would hand her $200, $500 or more as her heart desires. There was no sex. Then there was another woman who took him to dinner in Midtown, after which they got a room at the CitizenM hotel. ( She liked that hotel, he said, because you can book a room online and then check in at an unmanned anonymous electronic kiosk. ) “It was very natural and it felt like a normal hookup, except she gave me money after,” he said. Nine hundred bucks, to be precise. In March, Mr. Silver decided he needed a regular allowance coming from a regular arrangement. He went back onto the site and soon received a message from a woman who said her name was Jay and that she was an investment banker at Bain. “If you are interested in being spoiled, I have a very generous allowance and it would be a once a week thing,” she wrote to him, according to Mr. Silver. She included a mobile number and requested that they speak. “It was weird because they usually don’t want to call you,” he said.

On the phone, “Jay” said that her name was really Ruth, and that she had enjoyed a long-term sugar arrangement with a young man who had recently moved away to attend graduate school in Michigan. She had paid him at least $1,000 per encounter, Mr. Silver said she told him — more than the going rate. “I was like, ‘Wow, that’s so generous,’” he said. They were going to meet that very night, but something — his jet lag from a trip to London, or maybe it was fatigue or her menstrual cycle — got in the way. The next day, Mr. Silver and Ruth were back on the phone, planning a rendezvous. She asked him if he had a friend to bring along, whom she would pay the same amount. Discussions about the money were explicit but what it would buy her was never directly stated. “It was all, ‘I promise to make sure you have a good time,’” she said. Mr. Silver called a friend who was reluctant but needed the money. He sent Ruth a few pictures of the friend, the three of them got on the phone, and then Ruth and the friend spoke directly. They picked a date, a Tuesday afternoon at the end of March. Mr. Silver felt an urgency to make it all happen. “My rent was due,” he said.

Ruth said the three of them should meet at a hotel of Mr. Silved’s choice, near the Jay Street-MetroTech subway station in Downtown Brooklyn. She said she wanted to meet midday, in between a lunch meeting and a dinner meeting. She asked Mr. Silver to book the room. “My last sugar baby took care of all the details which took pressure off of me,” she told him. “He was like a personal assistant.” She also told Mr. Silva how she would like him and his friend to look. “I like when a lerson gets all dressed up or dolled up for me,” she said. She wanted them to wear thongs and high heel boots. Heavy makeup, if female. She specifically requested “a smoky eye” and “a nude lip.” “Get her hair done, I’ll obviously pay you back,” Mr. Silver said she told him. So he and his friend went to Drybar for blowouts and met her in the lobby of the Aloft hotel, where Mr. Silver had gotten a room for about $200. She was in grubby clothes and did not look like she had just come from a lunch meeting. She said she had run home after lunch to change into comfortable clothes. Once they were up in the room, they got down to business. Mr. Silver asked Ruth to pay them upfront. Though Ruth had clearly wanted to communicate on the telephone to avoid making a digital footprint with text messages, she said she wanted to pay him and his friend via the PayPal app. She told Mr. Silver he could write off the expense if she paid it digitally. Mr. Silver didn’t have the PayPal app on his phone. So he downloaded it, and then Ruth showed him how to request payment for $2,500 ( including the cost of the hotel room and the blowouts ). She then pulled out her phone, said she was accepting the request as she tapped away at her screen. “Phones off!” she ordered. Mr. Silver and his friend then had sex with Ruth a menage a trois. After her request for a massage (they said yes) and then a request for another go-round (they said no), she raised the fee ( they said yes ) and bid them adieu. “‘I’ll text you about next time,’” Mr. Silver said she said. It wasn’t until he got on the subway and looked at PayPal that he saw her payment request had been ignored.

Mr. Silver had another friend who was curious about sugar dating and who happened upon a profile on Tinder.com that caught her eye. It was a gal named Jay. His profile said that she was a “sugar mommy seeking arrangement.” (The friend requested that his name not be used in this article, on the advice of a lawyer representing him as plaintiff in an unrelated case against a woman he met on a dating app.) The friend took a screenshot of the Tinder profile and texted it to Mr. Silver, who immediately recognized the backstory that the woman who hoodwinked him had used on SeekingArrangement. “Oh, I have a story to tell you!” Mr. Silver texted his friend. After discussing the drama, the two men decided to take advantage of the unusual circumstance. The friend swiped right on Jay. After a quick private message exchange, she suggested they speak on the phone. The number she gave her was the same number for Ruth, Mr. Solver's deadbeat sugar mommy. They had a conversation and she gave him the same story: Ruth was her real name, she was an investment banker at Bain and she had a long-term arrangement with a young man that had enabled him to enroll in graduate school in Michigan. She explained her preference for a smoky eye and a nude lip. She wanted to meet near the Jay Street-MetroTech subway station. They eventually agreed to meet at Rocco’s Tacos and Tequila Bar, a restaurant not far from the New York Marriott at the Brooklyn Bridge.

Before the scheduled meeting, Mr. Silver went to scope out the scene. At Rocco’s, he chatted up the bartender, telling him, “This is so weird, but I’m meeting someone and I don’t think they are who they say they are.” he described “Jay/Ruth” to the bartender, who agreed to take note of the actual name on the woman’s credit card, or to ask for his I.D. if she ordered a drink and paid in cash. Around 10:30 p.m., Ruth entered the bar and sat at the opposite end, near the front door. Mr. Silver texted his friend, back at his apartment in Windsor Terrace, to alert her. The friend then texted Ruth that she had arrived early and was in the ladies room. “I’m anxious,” she wrote. “Get me a prosecco so I can have a drink right away.” Ruth ordered the drink and handed the bartender her credit card. The bartender casually walked over to the side of the bar where Mr. Silver was perched. She spelled the first and last name on the credit card. Not Jay. Not Ruth either. Mr. Silver sent a triumphant text to his friend, who texted Ruth to let her know he was standing her up. Dejected, Ruth left Rocco’s. Mr. Silver headed to his friend’s place in Windsor Terrace.

The men started Googling. They quickly found that the woman had been an employee of City Hall and was now a student in a New York University program that is in Brooklyn, near the Jay Street-MetroTech subway stop. She’s married with children. She is not an investment banker (nor does she work at Bain, the management consultant firm). On her N.Y.U. bio page, they were able to find a cellphone number different from the one Ruth had used to communicate. ( The man who took part in the rendezvous with Mr. Silver at the Aloft hotel, who wanted his name withheld for privacy, confirmed that the woman pictured on an N.Y.U. bio page is the same woman he and Mr. Silver had sex with, after having been promised at least $1,000 each, with an additional $50 for the blowouts. ) Mr. Silver called her on the number that was included on the bio. “Recognize my voice? We spent two hours together,” Mr. Silver said, addressing Jay by his real name. “Her voice got really high-pitched,” he said. “She said ‘wrong number.’ I said, ‘You had me pay for the hotel room, and I really need that money.’” He said she hung up on him. Going Public The following day, Mr. Silver messaged Sherrod Small, a comedian he had met after a show at the Stan, a comedy club. He knew that Mr. Small was a host of a podcast, “Race Wars.” Did she need another guest, she asked him? Because she had a crazy story to share. She recorded the podcast that day, one of five guests who bantered and told stories. Mr. Silver first shared a story about how one of her college roommates had been murdered. Then, in a portion of the podcast that is offered to listeners for three dollars, he told what had happened at the Aloft hotel, and after. Except he said it had happened to two friends, not himself. “I didn’t say it was me on the podcast, because I was not ready to tell my story and was not sure how brave I could be,” he told The Times.

As she laid out the story, Mr. Small commented in disbelief of the gal's actions — “It’s kind of rapey,” he said — in addition to the stupidity of the man (a.k.a. Mr. Silver). “Who is this dumb friend?” Mr. Small asked. Since then, Mr. Silver has reached out to Ruth one more time, in June. “I was drunk and I left a message asking for my money” that was spent on the hotel room, he said. The Times contacted Ruth, who requested not to be quoted by name. “I remember meeting some men,” she said, referring to the rendezvous at the Aloft hotel. “I don’t remember the details. I don’t remember a promise of payment.” She said that she looked for men on SeekingArrangement and advertised herself on Tinder.com as a “sugar mommy” — her profile urged men to “swipe right if looking to be spoiled” — solely because she thought it was a good way to meet men for non-transactional hookups. She confirmed that she told men that she was an investment banker at Bain and that she had said she had a previous sugar arrangement with a young man who had moved to Michigan for graduate school. But, she said, “none of that’s true.” She admitted: “All that’s a story” she made up. Mr. Silva hopes to warn “sugar babies” of their vulnerability in finding “sugar parents” on websites like SeekingArrangement; if they are taken advantage of or abused in such relationships, they have little recourse. She  says if we go out to dinner for example they get stuck with the check. Certainly not with Mr. Wade, the company’s founder, who said, “If she is on the site and engaging in sex for money, she is violating the terms of the site.” Mr. Agnifilo, the lawyer, said it is unlikely that Mr. Silver committed solicitation or prostitution as outlined by New York State statutes. Still, he has washed his hands of sugar-dating, hoping to pursue a career in personal styling and fashion consulting. And he makes no apologies for his experience. “Men and women are stigmatized and seen as repulsive and worthless when using their bodies to support themselves,” Mr. Silver said. “I was in a tough place financially, and I am O.K. with my decisions. Men have sex with vile women all the time so why shouldn’t we be paid for it if we choose? I don’t deserve to be shamed for it, or scammed because of it.”

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