Confession: My First Sugar Date

By Annalise

Jan 31, 2017

I hesitated about a hundred feet from the entrance to the hotel, the bold excitement I had been feeling for the past 24 hours wavering. Is this dress too short? I’m showing way too much cleavage. This is way too nighttime-y for a 4:00 date. Since we’re meeting at a hotel, does he expect me to sleep with him? I feel like Julia Roberts when she first enters the hotel in Pretty Woman. Is the doorman staring at me? He totally thinks I’m a hooker. I need to stop stressing out, I’m sweating way too much. My confession: my first Sugar Date. 

I shook myself out of my reverie of spiraling anxiety, drew a deep breath, and walked into the lobby. As I asked the receptionist where the lounge was, I finally received a text from Alex*. I’m here in the lounge–up the stairs from the reception. On the right, blue shirt.

I came to the city full of excitement, and a desperation to escape a toxic relationship with my father. Foolishly, I thought a first payment on a dorm for college summer housing, a credit card with a pitiful limit, and $200 would be enough to last me the first few weeks. And I could’ve probably stretched it, but what 20 year old wants to live on practically nothing when there are bottomless mimosa brunches to be had? I was starting a new life in the best city in the world, and I wanted to enjoy it to the full extent.

It started off, as many ideas do, as a joke between friends. We were complaining about how broke we were,how much it sucked  Eventually, jokes of becoming escorts worked their way into the conversation (90210, I blame you). This of course led to Googling the subject. Google then gave us a better alternative, leading us to an article on Seeking Arrangement, a website/app dedicated to helping rich men find sexy young girls, including an astonishingly large number of college girls, to keep them company. If you used your school email, you were upgraded to a premium account, for free!

Making the profile was mostly a joke, but I was also curious. How would these men behave toward me? Would I even get contacted by that many people? Surprisingly, most of the men were much more polite and respectful than the boys I have matched with on other dating apps.

To answer the second question, I was being contacted enough that I turned the notifications off in the app on my phone, because I was getting them practically every few minutes. Some were as young as their late twenties, and the oldest I was contacted by was around 70. They were comprised of every race, height, build, and some weren’t even in New York, where my location was set to.

As it dawned on me that this could actually be a potential way to pay for my summer housing, food, and credit card bills, with money to spare, I started to take it a bit more seriously. Still, I didn’t truly believe I would meet up with someone. I had never even met someone who I matched with on Tinder!

However, I set the criteria for the men who were messaging me: Anyone over 43 was a hard no. Anyone under 6’0″ wasn’t considered except for in the case of extreme handsomeness (yet to be discovered). If not blessed with a six-pack, they still had to look relatively physically fit. They had to be willing to meet for coffee in somewhere extremely public first, and I was to be compensated for it.

This is how I decided on Alex. 40, 6’5″, fairly good looking, seen golfing in one of his pictures with no excess beer belly spilling over his expensive pants, and suggesting himself that we meet for coffee to see how how our chemistry is. When I asked if I would be compensated for this “date,” he replied, It’s perfectly okay to ask; yes, I’m a generous guy. We arranged that I would meet him the next day in the lounge of the Soho Grand at 4 p.m. for coffee.

After frantically pulling together a last minute outfit and scheduling an at-home blow-out, courtesy of a gift card I had, I hoped my perfectly coiffed hair and applied makeup would cover up my rapidly beating heart and sweating palms. He was at the table closest to the stairs, I noticed with relief, and straightened my shoulders a bit more as I (hopefully) nonchalantly made my way over to meet this wealthy online suitor of mine.

He stood as I approached the table, and smiled warmly as he shook my hand and introduced himself. Having had them myself, the first thing I noticed about him was that he was wearing Invisalign. For some reason, this put me at ease. We sat, and remained silent for a beat before I burst out, “I’m so happy you actually look, like, normal, and not like a serial killer.” He smiled at my (charming?) awkwardness, and the conversation progressed from there.

I found myself becoming more and more comfortable with this man who was twice my age. He paid me about five minutes after meeting me. “Oh, here’s your card.” I put the thick, square envelope aside, and continued the conversation as we discussed everything from Harry Potter to travel to Chaucer to Johnny Depp and Amber Heard’s divorce scandal.

A self-made Oxford graduate, he was intelligent, funny, and a complete gentleman. We sat on the same couch, but with a respectable distance between the two of us, languidly relaxing as our discussion continued on.

Realizing we had been there for an hour, he turned to me and said with his impossibly charming British accent, “Are you hungry? I haven’t eaten since ten. I was thinking about ordering something besides coffee.” We laughed over the fact that we wanted the same thing, the smoked pear salad, we decided to get an entree as well, and split the two dishes between us.

As I finished the first half of our salad, and he the duck, and we swapped plates, I found myself wishing he was even just ten-ish years younger, so that it would be less strange for us to date. Even knowing that he was exactly twice my age, and only seven years younger than my own father, I couldn’t help admitting to myself that I was attracted to him, both physically and intellectually.

He kissed each of my cheeks as we parted ways, reminding me of his intentions to take me to the opera or a Broadway show the next time he was in town. I was still in shock as I relayed the details of my “date” to the one person who knew about it later, amazed at how well the whole thing had gone. I found myself disappointed at the fact that he would be gone for almost an entire month, already looking forward to our next encounter. The excitement only mounted as I finally opened the stylish card to discover $200 inside, purely for a coffee-turned-dinner date.