I Met a Sugar Sister on my First Sugar Date

By Katya

Jun 27, 2017

I met my first Sugar Sister in March of 2014, within days of moving to New York City. I’d become fed up with the lack of opportunity in the post-industrial upstate town I was living  in. I’d been accepted as a transfer student to a prestigious university in Manhattan. I spent all my money on moving, and was financially strapped upon my arrival. I’d recently heard of Seeking Arrangement, and decided to try it. Less than two days after moving to NYC I established plans to meet with a potential Sugar Daddy.


First Date Sugar

Joe* and I met for drinks on Manhattan’s Upper West Side. He seemed like a kind, sane individual who was willing to be generous. He was in his late forties, attractive, and had an established career. After a few rounds, Joe asked if I would like to retreat to his apartment for further drinks and conversation. I obliged.

Joe lived in an upscale doorman building. Having come from a small-town, modest upbringing, I was wowed. Moving to New York City exposed me to vast wealth for the first time. Until then, I’d only seen such extravagance in television and movies. Upon entering Joe’s spacious, luxurious apartment, we sat down in his living room. Not wanting to come across as unsophisticated, I tried not to act too impressed by my surroundings.


A Man With Options

“Anna!”, yelled Joe. “Could you bring us some drinks, please?”

A few minutes later, a gorgeous, brown-eyed woman with long, dark hair and a curvy figure entered the room with a tray containing an array of wines, beers, and spirits. I selected a drink, thanked her, and she exited the room.

“Who’s she?”, I asked curiously.

“Oh, she’s my personal assistant”, Joe replied nonchalantly.
For a few minutes, Joe and I continued our conversation. Suddenly, a landline phone rang. Anna answered it, and said to Joe, “there’s a woman here to visit you, Tanya something?”

“Oh, shit”, replied Joe. He looked at me nervously, and said “I forgot that I scheduled for another girl to come over tonight.” Nevertheless, he gave permission for Tanya to come up to the apartment.

I was instantly overcome with anxiety. Anticipating an awkward verbal confrontation with Tanya, I gathered my bag in preparation to make a quick exit from the apartment. Before I could make my way out the door, Tanya arrived.

At this point, I didn’t know what else to do, so I introduced myself to Tanya. She had a polite, calm demeanor, despite seeming surprised by my presence. She was a Sugar Baby who’d seen Joe in the past. Over the next hour or so, we warmed up to one another quite well. We talked mostly about our lives (past and present), with Joe intermittently chiming in with advice and to talk about his experiences.

As positively as things went between Tanya and I, Joe’s behavior became bizarre. He’d been drinking heavily, and it was starting to show. His words became slurred, and his statements became less coherent. We encouraged him to take a break or slow down, but like many intoxicated people tend to do, he insisted he was fine.


Drink Responsibly

Joe left the room and went to his kitchen for another drink, while Anna was involved in some other task. While Joe was in his kitchen, Tanya looked over at me, rolled her eyes, and said “girl, let’s get out of here”. We didn’t feel unsafe, but it was clearly time to end the night. Tanya had me take down her number and said “we should be friends, especially because you’re new here. I’m a native New Yorker, and I can help you get accustomed to living here. And I don’t feel comfortable talking to many of my friends about this Sugar Daddy stuff, but now I’ll have you.”

Upon Joe’s return to the living room, Tanya stated her intentions to leave. Joe handed her a wad of cash, and called Anna into the room. “Go to the ATM, and pull out $400.”


Not the Arrangement I Came For

Tanya waited with me until Anna returned to the apartment. Anna handed me a wad of cash, which I thanked her for retrieving. I thanked Joe for his generosity, which I wasn’t expecting on a first date. Tanya and I talked while heading to our respective subway stations, and made tentative plans to hang out again soon, without a Sugar Daddy being present.

I never pursued an arrangement with Joe, and Tanya ended their arrangement shortly thereafter. It wasn’t personal, but we’d both been turned off by his heavy drinking, along with his seemingly accidental scheduling mishap. We were thankful that it led to us meeting each other, but knew it might happen again in the future with another girl, and that things may not go as well. To avoid potential drama, we moved onto other Sugar Daddy pursuits.

Tanya judge, they also couldn’t relate. It felt nice to be open with someone who understood firsthand what Sugaring is all about.

To this day, Tanya remains one of my closest friends. Both of our lives have changed drastically since that night. She’s moved onto becoming a mother and seeking a traditional relationship. I’ve decided to participate in the Sugar Bowl on a much more limited basis than I ended up doing shortly after Tanya and I first met, while focusing on establishing myself in my chosen career field.

Despite my first Seeking Arrangement date with my first Sugar Sister and now best friend, but I couldn’t be happier that things turned out this way!

*Names have been changed to protect the privacy of individuals.