Finding My Perfect Sugar Daddy

26 Sep

I decided to enter the sugar world on a whim. The thought came to me in a cafe and I traipsed home, determined to find out more about being a courtesan (I didn’t know the term sugar baby existed). I google-d information on courtesans, read through their websites, personal blogs, as well as the websites of escorts. None of it seemed quite right. I was looking for more of a traditional mistress-type role, something on-going, with a slight emotional connection but none of the obligations and trappings of a traditional romantic relationship. Oh, and I wanted single men.

So, I searched until I came across the concept of a sugar relationship. It sounded like it could be something I could do. That night, I signed up for,, and The latter received the most e-mails, but I wasn’t able to check them until I paid. Reviews here.

For the next two weeks, I spent all my free time sugar daddy hunting. Responding to e-mails, chatting on the phone, exchanging texts, and arranging dates consumes serious energy and time. I began an Excel spreadsheet to keep track of everyone and wrote down every detail as soon as it happened. The spreadsheet was super helpful since sugar daddies tend to be crazy busy and some will express interest in you, but need to go away for a few days or so. Writing down the little details helps you pretend you remember everything they do and all the stuff you’d previously talked about.

I went on so many sugar dates during this time. Sampling restaurants around the city was great, but most of the men I met were really not appetizing.

I met a doctor I had corresponded with via email. He seemed incredibly sophisticated. He was a fellow bibliophile, expressed concern and consideration for my transit to and from dinner, and his idea of an ideal arrangement mirrored my own. Then we met. He was clinically unattractive. On the other hand, he was a really sweet guy and the dinner was enjoyable. Until he started talking about how he wasn’t ready yet, but later I would bear him children. Ummm, no.

I also met a European guy who was soft-spoken and shy. Perfect for me, I love introverts. But I just wasn’t physically attracted to him at all. His shyness wore off 30 minutes into dinner and he declared he wanted an arrangement, then proceeded to press me for it throughout dinner. He gave me my first taste of sugar afterwards. Just pulled out all the bills he had in his pocket. It wasn’t much, a few hundred, but it was a happy feeling. A feeling that this does actually work. Over the next few days, he text-ed me in 5 minutes intervals until I snapped and blocked him.

Another guy I met was a single dad, sweet but really nervous. He went off on a monologue about something (the past?) and it was pretty obvious he was not comfortable with the whole thing. He was quite cute though.

I met a bunch more that I don’t quite recall…maybe I’ll consult my spreadsheet later.

Anyway, I started chatting with a guy in NY. We had a lot in common. I could tell from his phone manner that he was circumspect, introverted, analytical, prone to monogamy, and as cautious about sugar dating as I was. He seemed to like me too. He wanted to fly me out to see him immediately, but I was hesitant. It’s always better to meet someone on your home turf first. What if he turned out to be a psycho? Well, I googled him, did a reverse phone search, etc. He checked out. We talked more often. He offered to fly me out again and I decided to go. Good news: he was not a psycho. Bad news: he was really unattractive.

I don’t consider myself superficial. Some of my ex-boyfriends have been questionable looking and I can usually fall for a guy’s brain. But…I knew I wasn’t ever going to be attracted to this guy. And this really should’ve ended there. Yet, I’d been on the sugar dating sites for about 2 weeks by then and I knew genuine guys with sweet personalities were rare. Plus, we had similar interests so conversation was so easy. He proposed an arrangement during dinner. I said yes.


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