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I’M WITH CUPID – How I Impersonated a Man on a Dating Site




How I Impersonated a Man on a Dating Site

Text and Illustrations by Girtrude Belle

Sometimes I take up strange jobs. And so one winter  it came it pass that I took a very strange gig indeed. It entailed impersonating a guy who found online dating tedious and time-consuming and who was willing to pay me an hourly sum to do it on his behalf. Yes, to play him on the internet. It was part acting, part writing, part social research. In short, I couldn’t say no. Plus, I love jobs you can do in your underwear.

I read the dating profile he had created to get an idea of his tone and sense of humor. I interviewed him about the types of women he likes, looked through a bunch of their profiles along with him, and eventually a picture of his preferences emerged. He’d never go for someone who wears a baseball cap non-ironically. He’s not into people who look too exotic. He relates more to European exiles. He won’t like legs this muscular. He prefers more feminine facial features, no strong jaws. Anyone below 5’5” will be too short for his taste (in porn parlance, he’s not into “spinners”). This one’s too geeky. This one’s too gawky. The list went on. And suddenly I had become…a successful dude looking for a hot girlfriend.

Prior to having taken the point of view of this virile, handsome, intelligent man, I had a rather generous view of what makes a woman beautiful. For one, I had lived in a good number of cosmopolitan cities, where women knew how to appear presentable. Most of them were relatively hip. Most had goals, interests, hobbies. In short, most of the women I had been lucky to observe in my life had a clue, and this made them attractive. Then there was all the other stuff.


“It’s important to note that, when it comes to dating, there are two types of men…”


Like Bill Clinton famously, I am a person who tends to find something appealing about everyone I meet and to compliment them on it without hesitation. I do this because I can’t help it, not for any other reason. I notice, for instance, that some girls have beautiful hair. Others have luminous skin. Some have a great cleavage. Cute perky boobs or nice shoulders.  Tiny athletic butts. Luscious rounded thighs. Huge sexy mouths with perfect rows of teeth like a toothpaste ad. Perfect feet. Some girls move so well you can’t stop watching them. Some just have great posture that’s worthy of admiration. Others have  sexy voices, or eloquent diction, or a charming way of enunciating. Some are so sweet their sweetness is infectious. Some are so sharp their astuteness keeps you guessing. Some are naturally and devastatingly chic. Some have killer haircuts. Some can sing. Others have interesting jobs that endow them with dignity. The list of what could make a woman sexually attractive was seemingly endless. Until I became a man.

Now it’s important to note that, when it comes to dating, there are two types of men (yes, I know, sorry). One is the connoisseur – the guy who, like me (and Forrest Gump), sees life as a box of chocolates and every woman as a special truffle to be gently picked up, sniffed, examined, unwrapped, licked and only then placed in one’s mouth for a bite or two. This man enjoys his gift for discerning what makes each woman special. And he very much enjoys honing this skill by tasting every kind of truffle. Because he’s a consummate gourmet, there is no truffle he doesn’t find at least intriguing. Heck, he’ll even give a moist raisin cookie a chance every now and then.


“The list of what could make a woman sexually attractive was seemingly endless. Until I became a dude.”


The second type of guy is the Type Guy. He’s the acquaintance whose taste in women you know so well you could play matchmaker for him in his absence. This sort of man is more common. Most guys I know fall into this category either by choice (or Freudian proclivities, if you don’t believe in free will) or necessity (i.e., that’s pretty much the type of woman that tends to go for him). I have the friend who goes for petite mousy-looking girls with quietly demanding personalities. The friend who goes for stout big-eyed brunettes with artsy proclivities. The friend who goes for long-legged plaintive divas-on-the-rise. The friend who goes consistently for unavailable women half his age. The guy I was called upon to impersonate was definitely a Type Man. He was bright, accomplished and sufficiently good-looking to aim for the kind of woman (girl, to be more precise) that most people, and television-sitcom talent scouts in particular, would consider to be Coltish-Doe-Eyed-Young-Leading-Lady material (addendum: who sorta knows she’s way hot).

And suddenly a switch flipped. Girls who, as a mostly-straight female, I’d find to be objectively good-looking (good skin, good hair, good features) but whose smiles were a little too big now began to look “horse-like” or excessively and annoyingly “eager.” Suddenly I began to notice a lot of what looked like “crazy eyes” on otherwise pretty human females. I also started noticing with a great deal of annoyance that a lot of women were designating themselves as “thin” in the body type category who were not thin by any stretch of the imagination. They were, well, regular. Maybe thinness is in the eye of the beholder but my beholder liked his chicks slender indeed, and all this body-positivity suddenly struck me as false advertising. I caught myself getting kind of pissed off: good for you, you think you’re thin, well guess what, nobody else does! What was happening to me? A second ago I found everyone beautiful and suddenly I had become a model-monger. FML.


“Are there, in fact, people who consider their own sense of humor unfunny?”


There were many things hitherto unremarkable that in my picky role as a dude now irritated me. For instance, I began to notice with some dismay how many women listed a good sense of humor as one of their “requirements” in a man. Either that or some variant of “he must make me laugh.” You might not make much of this, but as a guy I felt indignant. First, why should I, a man, be required to entertain you? I’m not a clown. Besides, what sort of consumerist attitude is this? And what, pray tell, do you bring to the table – the ability to giggle? Second, what response to this are you looking for? Am I expected to open with my best stand-up routine, my latest one-liner, or should I rather inform you off the bat that I am a humorless dolt? Are there, in fact, people who consider their own sense of humor unfunny? Never mind that anyone who asks point-blank for a “good sense of humor” probably hasn’t got one and so, as a dude, I probably didn’t want to date them.




Once I did select a few lucky hotties with whom to strike up a conversation, I had to be careful to avoid commenting on things my guy would never notice – like the stylishness of someone’s backpack, or which he wouldn’t find too important – like their cool artsy photos. I began to eliminate filler words such as “somewhat” from my sentences, thinking that they didn’t sound assertive and, therefore, manly. I instinctively used less “smilies,” sensing that a man is valued more for his reserve than his agreeableness. I felt that too much back-and-forth chatting would land me in friend territory rather than in Mysterious Sexy Stranger territory, which I thought preferable in the circumstances. For the same reason, I opted for brevity, thinking that the less I say at any turn the more I leave for the imagination. And yet I wasn’t very serious in tone, thinking that silliness is an unthreatening precursor to sexiness. It worked. Most of the hotties I pinged agreed to dates, with the occasional exception of those mega-hotties whose mail..*cough*..boxes had reached their allotted limit. And whose self-assessment had probably done the same.

As for my dude, he never went on any of the dates. Neither those that I had set up, nor those I’d passed on to him to follow through with. Apparently online dating wasn’t just tedious for him, but also not all that appealing a medium. I can relate. For some reason, I find the whole process of “dating” to be onerous and reminiscent of interviewing for a job. Or maybe the romantic in me simply refuses to believe that love and connection are about statistics, effort, and software, preferring instead to entertain notions of serendipity and happenstance. You’ll be glad to know that now, a year later, our dude is happily coupled to a girl who both suits his type and with whom he shares a somewhat convoluted and charming accidental-love story. IRL. As for me, well, this story isn’t about me, now is it?

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