Damnit, Cupid, SO NOT OK: The OkCupid Trials, Date 1

I first joined OkCupid back in December of 2009. Back then, I was working full time, I had my own apartment, and I was more of a developed adult than I am now. The only thing that was missing from my grown-up life was a boyfriend – so one night, I created an online dating profile, and the hits started coming in. 

By ‘hits,’ I definitely mean ‘weird messages from dudes who were clearly single for a reason.’ Every girl on OkCupid attracts a different sort of unsavory suitor. Mine can be described only as ‘gym-rat muscle heads with disproportionately shrunken heads,’ and there were definitely a bunch of messages from them, but there were also lots of cute guys to meet, so I started booking dates. 

I went out with around 10 guys the first month I was on the site. The first one seemed like a laugh riot online, but when we met up in person, I was startled by the fact that he had an unnaturally shiny, red face and an incredibly high-pitched lady’s voice. Seeing how I have a deep voice for a woman, it was deeply unnerving to be on a date with a guy who spoke in a higher octave than me. We went to McSorley’s, where I was forced to squeeze into a seat right next to the wood-burning stove or whatever that thing is. Predictably, I managed to lean against said maybe-stove and give myself a third degree burn on my tender, fleshy bicep. Date foul, for sure. We said goodbye on the subway and I’m pretty sure he gave me a high-five to end the night, which suited me just fine, except for the fact that his hand was simultaneously clammy, cold and smaller than mine. 

In which Caroline tries to make sense of something awesomely weird on OkCupid.

Just now, while skimming through OkCupid profiles how I do, I happened upon a rather promising potential date: 22, male, over 6 feet tall, good taste in music/books/movies and cute AS. I was about to rate him highly in the hope that we would forge a love connection – but then I saw his gem of an answer to the standard OkCupid prompt “most private thing I’m willing to admit here”:

My ideal partner would be a woman who is into pegging.* I’ve never been attracted to guys, but I would love to be some girl’s bend-over-boyfriend.

*Pegging is a sexual practice in which a woman penetrates a man’s anus with a strap-on dildo, says Wikipedia (in a grossly clinical and graphic way).

WOAH. Seriously, WOAH. Most people respond to that prompt with a funny little anecdote about their childhood or a statement like “the fact that I’m on this website.” THIS dude decided to respond by confessing to wanting to be done in the butt by a girl with a fake dick. I mean, I’m all about being candid, but DAMN.

I have so many questions for him. Did he not look at anyone else’s profile before he made his own? Has he not realized that, for the most part, the people who discuss such things on said website also have a proclivity for carrying around a filthy duffle bag filled with chloroform and sturdy rope? Or is he simply making it clear that he exclusively wants to date a girl who enjoys beat poetry, cooking farm-to-table dinners and wearing strap-ons?

It’s not the fact that he wants to be pegged that is boggling my mind. Hey, man – you do you; I’m not going to judge. His fantasy isn’t even that weird, in the scheme of things. It’s just…what if he’s never talked about this before, and then someone he knows sees him on Quickmatch (which happens ALL THE TIME) and then every time that person looks at him all they’ll be able to see is him with a ball and gag in his mouth getting pegged??? I’m so worried!!!

Then again, who am I to talk? I used that prompt as an opportunity to brag about how I built my soundproofed, cedar-lined S&M dungeon ALL BY MYSELF in ONE WEEKEND. Isn’t that impressive, though?

UPDATE: Here is YET ANOTHER “most private thing I’m willing to admit here” that talks about PEGGING!

My New Years Resolution was to be more honest, so here goes:

I am a cross dresser. It’s not that I want to be a woman, I just
really enjoy wearing womens clothing. I am also quite bi-curious
though I’ve never actually been with a man, yet. I don’t want to
list myself as bi on here, because I’m not sure I’m ready for that
stage of my life at this moment.
As things are now, I have a strong fetish for pegging (where you,
the woman would wear a strap on and I would wear a dress
and…well, I’m sure you can imagine the rest). Again, it’s not
that I want to be a woman, but gender reversal and male anatomy
highly interest me. I feel that this is something that’s very
important for a partner to know about me right from the
start.
Whew. I feel better now!! Here’s to 2010!!!