About That Time I Dated a Penis Doctor: A Chronicle of Online Dating in New York City (Part 1)

It can only be a sign of strange coincidence that as soon as I agree to write a column about online dating, I close up shop. That’s right, CupidGal has a CupidGuy now, thanks to a little site we call OKCupid. And it’s just as wonderful and exhilarating and terrifying as I expected. But on to that in a little–now’s a time to reminisce.

Making that final goodbye “click” on the OKCupid profile, CupidGuy doing the same next to me, was a weird sign-off to a part of life here. Because perhaps no other part of my life has provided me with as much entertainment, hilarity, and growth here in New York as online dating has.

Awestruck friends tend to ask how I have so much luck in online dating. But let me be very clear: online dating isn’t a talent. It’s an opportunity. And so I answer that the reason I’ve scored great dudes (yes, plural) from OKCupid is that I said yes 99 percent of the time. If a guy that has caught my eye, even just for a moment, wants to go out, I’ll say yes. And yes, that has led to some incredibly uncomfortable, weird dates. But I’ve never regretted a chance I didn’t pass up.

[Sidebar: That being said, I also say to know when to say no, too. A “no” is as equally important as a yes. Because if your gut tells you not to trust a man–your gut is right.]

And so, here is a roster of the dudes I said “yes” to over the past 1 ½ years, starting with the most recent. Yes to romance, yes to lust, yes to time-fillers–yep, it has been kind of a mortifying and thrilling ride.

1)   The Penis Doctor:

Ok, not a true penis doctor. He was a resident in urology. Still, the subject of penises came up within the first 20 minutes of the date, because what else are you really going to do when you ask, “So what do you do?” and he responds “I’m a urology resident … so yeah, I spend my days learning about penises.” Besides the fact that Penis, MD was in fact very charming and sweet (like preppy Southern boy sweet), I highly recommend dating anyone in urology. They’ll answer any of the questions you have about ding dongs because they’re genuinely excited to talk about what they do! Penis MD was in fact a great guy.  Actually, I was seeing him when I met CupidGuy. It was a tough choice, but it ultimately boiled down to chemistry. Despite our common love of music and, uh, male genitalia*, his wasn’t the junk I was after.

2)   Habitual5.

Not his real screen name, but I literally don’t remember his name. He tried to booty call me on the Lower East Side when I said I’d meet up with him one weekend, and I never heard from him again. I blame this one on the fact that I really can’t say no to a guy with a good beard. I am the most stereotypical faux Brooklyner ever.

3)   DocFuzz-something.

A no-name doctor who couldn’t have been more boring.

4)   Production Assistant.

The PA was one-part romantic possibility, one-part time-filler, one-part what-was-I-thinking-disaster. Initially, it was the chemistry that drew me in; we couldn’t keep our hands off each other from date #2. The nonstop texting and sappy compliments helped heal my bruised ego from a heap of recent failures and insecurities. And when I got pink eye and the flu on New Year’s Eve, he stopped at nothing to rush over, pizza and champagne in hand, and let me fall into a Nyquil-fueled deep sleep while we watched Game of Thrones. Still, it became very clear that chemistry could only take us so far. We had nothing in common, besides the fact that we both liked sex. And when dinner dates turned into sweatpants on the couch with takeout, I realized that the TV only camoflaged the fact that we had nothing to talk about. He stopped texting; I stopped caring.

5)   Writer for a little magazine that rhymes with The Blue Porker.

(Which sounds like a variation of blue balls, which I swear is only a coincidence.)

While trying to figure out the PA and what that all meant, the writer floated in on a cloud–at least that’s how it felt. He was everything I wanted, on paper. Which made it much more devastating when he called after two dates to say he wasn’t interested. I tell myself that he was short and a hands-down terrible kisser–and also, writers are the worst. Seriously, have you been out with a writer? Egomaniacs! There can only be room for one in a relationship (meaning me–I’m the worst).

6)   A fellow hippie-musician from my home state, who couldn’t have been more charming … online.

He said he was going on tour, and then he never messaged me again.

7)   The software engineer.

Brooklyn chewed up and spit this guy out. The pros of dating a hipster: bearded gorgeousness, check. (I mentioned I liked beards, right?) Making out in divey, dark Brooklyn bars, check.  Cons: Dudes that are pretentious and cold and indifferent to human emotion? Check, check, and check. He stayed over one night, I made him granola (which probably wasn’t up to his Brooklyn standards) and I never heard from him again.

8)   The voiceover actor / bass musician / 37-year-old-pretending-to-be-a-30-year-old.

(Tip for lying to ladies, dudes – don’t show her your license! If she has a brain, she can do simple subtraction!)

Remember that part in Sex and the City where Carrie dates the bass musician who “plays” her? I’m embarrassed to say I fell for that. One-night stand, never to be heard from again–fortunately.

9)   Upper East Side lawyer / New Englander hippie.

One stellar first date, including lots of beer at a beer garden and making out on a gorgeous summer night, turned into one month of phone tag and drunken texts trying to meet up. When he finally admitted that he was looking for just sex, I drunkenly texted him that he wasn’t worth my time–the best drunk text I’ve ever sent.

10)   The businessman headed west, and possibly the only guy that I still wonder about.

Chivalrous, sweet, worldly, this guy had it all. Of course, one week after we met, he told me he was moving to San Francisco for his job at the end of the summer. Didn’t stop us from having one great summer fling, though. He was a reward from the three douches that preceded him–part two of my dating chronicles. Stay tuned.

So not exactly a stellar line-up of dudes–they would probably make up a sad and hilarious baseball card collection. How’s your roster looking?

* Just kidding–a common love of male genitalia probably isn’t a good thing to share in a relationship. Pretty sure my high school boyfriend who came out of the closet in college would agree with me on this.

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