What It's Like To Go Out With A Sugar Daddy

I was recently approached by a dating site specializing in helping Sugar Babies and Sugar Daddies find each other. According to the site, a Sugar Baby provides companionship in exchange for being pampered, while a Sugar Daddy pampers Sugar Babies in return for companionship. After poking around the website for a while, I was intrigued. A lot of the men on the site's glossy homepage looked like healthy, well-rounded people — not old, lecherous, perverted Internet creeps who can't get a date without flashing their wallet around — and so I responded to the letter.

After a long back and forth, I agreed to go out on a date and interview one of their most eligible Daddies. I was told that they'd pick someone who was a good representation of their client-base — not some Richard Gere lookalike fantasy who would make me feel like a Pretty Woman for the night. As someone who is deeply interested in modern relationships and the types of love that are born of the internet, I was curious about the website and who was on there.

The night of my date I was given an address and a thumbnail photo of a man that looked a bit like soccer player I saw on a jar of salsa during the summer of the last World Cup. Alas it was too small to see, and I assumed the picture was taken at least 10 years ago, anyway. I was told he would be called John, and we would be meeting at a small tavern in Tribeca. Earlier in the day, I made a list of questions. The list was over seven pages long and ranged from general questions like "how has your experience with the site been so far?" to invasive questions like "do you feel like you're giving away a piece of your soul and dignity when you transfer money from your bank account into one of theirs?"

By the time I actually showed up to the interview, my palms were sweating and I had forgotten everything I wanted to say. When a thirtysomething man in a neon green Lacoste teeshirt came up to me at the bar, I told him the seat next to me was taken. "I'm, yano, 'John'," he said "I Googled you so, I knew what you looked like," he said, awkwardly shifting his weight and tugging at his nose — perhaps a nervous tick. John was tall, fit, handsome, with an innocent boyish face. Despite my obvious shock, we quickly shook hands, let out a few forced laughs, smoothed out our shirts, played with our hair and moved over to a table in a quiet corner. I ordered my third glass of wine when he ordered a glass of top shelf scotch.

Over the next two hours, John and I talked like old friends. We talked about poetry and politics and the craziest things we've seen on subways. We talked about our aging parents and New York City loneliness. We talked about Tom Cruise and Scientology and Ancient Aliens and The Food Network and the best falafel in Brooklyn. We talked about the many different types of bread and the lingering complexity of Vanilla Sky — whose voice is that in the end? Before we knew it, John was on his fourth scotch and we were slapping our knees and cackling with tears in the corners of our eyes. And then, after a brief post-laughter lull, John slipped, "So the casting director said you'd have some questions for me?" "Casting director?" I asked. His face sagged. "I mean, the lady, the woman, um, the person who set up this date, our matchmaker..." he attempted to salvage it.

Wait, is this a real date?

When I asked what he meant, he explained that he was prompted by a "casting director" about what he should say about the site before he met me. While he was a member of the site, which I later confirmed when I saw his profile on there, I was disappointed that he didn't seem like a proper representation of the men on the site. Was I getting a real Sugar Daddy experience?

We shook hands and went our own ways. I wanted to figure out what exactly was going on here, so I did what any half-ass journalist of the internet does, I made an account and waded through their database. I wanted to know who used it and why.

Within the first hour of having my profile picture approved, I had a dozen messages in my inbox. Mostly older, white men, ranging from 40-70, looking to "spoil me," and a few international men with broken English and upfront money offers in exchange for Skype-sex. Yes, these were the Sugar Daddies I had in mind. I went through their profiles, one by one. Some of them were married and looking for some fun on the side. Others were world travelers who didn't have the time or patience for dating and wanted to know they had a open-legged woman ready for them when they touched down in whatever city they were headed to. That's why the money was OK for them — it was a business transaction, and that's a language most of these men understand. Paying for a service, the girlfriend experience. All the perks of a relationship — affection, attention, sex — but none of the emotional baggage that comes with it.

After a few hours, I had slipped into a dark web hole. I wanted to find out how disgusting and degrading and sexist these men who use the site are. But then I read through some some my messages. And a different feeling set in. Sadness. And then my initial question returned: Is this wrong? Most of the men in my inbox were not pigs, they were lonely men who will pay anything to feel otherwise.

So, I dragged the text from the messages from my inbox into a word document and cut and pasted them together in a language I know best, poetry. Because for me, poetry is a tool used to express the darker thoughts and every melancholy note between. I wanted to free these words from the context of the website. I wanted to answer my own question with their words. Is it wrong?

Here are 19 poems, directly collaged together from my inbox.


I’ve just given you accessto my private photos,go to my profile to view them. So, what do you think? Hello?Are you there?Take a look at me, please?


I am very fitand athletic,super healthy,and have a Richard Gere kind of look... Seriously.


I enjoyed your profile..and your photos.. you’re stunning..Interest piqued...let me know....


You look amazingin your pics.I am not looking for emotional disconnection, I am looking for an authentic person.Physically,I'm into fit girls with some curves,shocking, I know.


I’m intense, generous, affectionate and have a lot of love to give.I've reached the topof a very competitive fieldand I very much enjoy helping people reach their goals/achieve success.I’d like to help you, too.So, let’s make an arrangement that works for both of us. Do you understand?


Respected Goddess I kneel and kiss Your shoes and present myself as Your pet for Your use. Please guide me Almighty. I live in Beacon and work in Manhattan. I can run errands for You, be Your driver at Your beck and call and shine Your shoes. Will always do my best to fulfill Your orders.


Your servant


I really liked your profile and I’m hoping you'd agree to meet for some vintage wine and Swiss cheese


Brains are my # 1 priority .. I'm a lawyer, and a fun, friendly, attractive, in shape, adventurous, and sweet man. One thing you should know: Is that I'm married. If that's ok with you, we should talk.


I have everything I need in life except intimacy with a beautiful, intelligent woman like u.


As for what I am seeking:A special friend whom I can helpin whatever way she needs,a companion for whatever mischief we contrive,and a lover. . . all without emotional blackmail.


I’m no immature hipstersearching for himself,coding in his underwearat home or making artisanal beer or chocolate.I like living a nice lifestyleand sharing it with fun people.Do you want to meet tosee if our requirements can be met?


if you will marryand have kids with me. I can support you, okay?think about it.


sadly, given the public nature of my profession, I refrain from sending out pics ....but my mother used to insist that I was unbearably adorable


how about a fun and generous sugar da$$y? 1st of the monthwith just weeks to the Holidaysmakes for daddy time,doesn't it?Hit me up if you are ready,willingand able.


You look beautiful -

and I get compliments on my looks often, so that may give us natural chemistry.


I hope you like older men. Here is my story:I am marriedbut have not had intimacyfor too long.I love to be romantic,go out for long dinners, cuddle,kiss andmake love -ever so slowly.I am not looking for a hooker butI would love a long term affair.


Help me help you. I want to put a little Honey in your life. Maybe we can make each others lives a little Sweeter.


Did not hear back from you so, assuming you’re not interested.

Hello? Are you interested? Hello? I assume you’r not interested.


You don’t seem to be clear in what brings you here. Care to explain?I’m not sure what you’re looking for.NeverMindIt doesn't matter.

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Image: Kaitlyn Wylde