I found Seeking Arrangement and sites like it to be quite intimidating. My fellow prospective sugar babies all seemed to be skinny, tanned blondes. They were all exactly what I was not. I decided that since I’d already had such luck with Craigslist, it wouldn’t hurt to post an ad on there. I wasn’t expecting much of a response, but I was pleasantly surprised when I received quite a few. With all the emails pouring in, I was pretty sure that at least one or two of them would be what I was looking for. I was well on my way to becoming a kept woman of leisure.
The men who replied were far more diverse than those who replied to my advertisements for prostitution. There was a professor who wanted a girl to take on foreign trips, something that reeked of axe-murdering to me. There were a lot of men who simply wanted a prostitute–men who clearly didn’t understand the concept of a sugar daddy/sugar baby relationship–and a lot of obvious picture collectors. I narrowed down the candidates to a tattoo artist named Tony and a sixty-five-year-old testicular cancer survivor named Dennis who attached a picture of himself dressed as Hunter S. Thompson.
I decided I should go on my first date with Tony the tattoo artist. Because he was only in his thirties, I assumed his finances probably weren’t equal to the older man’s, making him a great candidate for a practice run. We exchanged numbers and made a date for dinner at some Italian restaurant of his choosing. I never got to the restaurant. About half an hour before our date, as I was walking to the train, he cancelled and, in doing so, made it abundantly clear that he didn’t realize this was more of an interview than an actual date.
But Tony was neither old, nor completely unfortunate looking, so when he texted me the next day–apologizing profusely and offering to take me anywhere I wanted–I gave him another chance. No, he wasn’t really my type at all. And no, he didn’t seem to understand that ‘sugar daddy’ wasn’t just some outdated term for ‘boyfriend’ from the 1920s.
But if I could get some free dinners and possibly tattoos before I even put out, I couldn’t really count it as a loss. After all, wasn’t that what most people call ‘dating’ anyway?