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.
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.
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
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.