Diary of An Online Dater

I am unashamed to admit that I am a former online dater. That’s right; OkCupid held me in its clutches and let me tell you, there's a reason it's not called "Super Awesome Cupid" instead. But in the spirit of finding true love, I never gave up — even when an illiterate Nigerian "prince" messaged me looking for money. I was, come hell or high water, going to find someone who didn’t suck.

During what felt like an epic piece of Greek drama, I assumed four different profiles on OKCupid, each projecting a certain identity. I tried to alter my personality — I'm sexy! No, I'm cute! I take selfies! I don't take selfies! — until I realized that the only personality worth inhabiting was my own. Over the course of this time, I met 38 men. In between all of the disappointed cab rides home, bad kisses, and inappropriate comments (“You look like Anne Frank!”), I came to a lot of conclusions about the Internet dating scene. In order to succeed, you’ve got to think of the Internet as a bar — albeit one where it’s OK to wear sweatpants, eat peanut butter out of the jar, and drink an entire bottle of white zin while approaching your prospective mate. Much like at your favorite watering hole, there are bound to be all sorts of distinct characters — the wallflower, the life of the party, the sexy stranger. So the big question was, what role would I play? How did I want to present myself?

1. What picture should I use?

My username was "mssmallfry" — “MS” for Mallory Schlossberg, and small fry because I am 4'11". I then had to select a profile picture, which carried far more weight since I knew many users would judge me based on my photo alone. I chose a picture of myself laughing, but it wasn’t like, the greatest picture of myself every taken. You could see that my teeth were sort of coffee stained and that my hair’s a little frizzy. I immediately saw the case for the not-great profile picture: I didn't want people to be surprised when they met me, so it was imperative that I look like my picture, but I also wanted them to be like, “Whoa, she’s better looking in real life!” — which is way better than "You're really, uh, photogenic!"

As soon as I started meeting people, I realized that I didn’t care if someone confessed to being bald or having a potbelly; it was the unpleasant surprises I didn’t like. Like, 5’6’’ is apparently guy speak for 5"1". I didn't want to mislead my potential mates. I never lied about my height on my profile; I’m not even five feet tall, and whoever met me was sure as hell going to figure it out, so what was the point of lying? Wasn’t the whole end game here to actually meet people in real, human form and find someone who is into the IRL version of you?

2. How do I talk about what I'm doing with my life?

At the time, I was just out college, so I was temping, going on auditions (ah, the dream of being an actor!), writing, and let’s just be honest — dicking around on OKCupid for hours upon hours. I had never been privy to so many men! So I suppose saying I was “pursuing my dreams” was suitable.

I forgot one super important, and kind of mortifying detail. The site required that I list where I lived...and I lived with my parents. I was a month out of college, and my parents lived in suburban New York, which meant I was a hop, skip, and a jump from New York City, but it also meant that I did not live in New York City. All of my very important temp jobs were in the city, so traversing around the city gave me some sense of autonomy, but I did not have an apartment. I had somewhere around $287 in my bank account. And I lived in the suburbs. But I wanted a city man! So, despite it being not entirely accurate, I said my city was "New York, New York," out of fear that a suburban girl who lived with her folks would not be an even remotely plausible option for city guys.

3. What am I looking for?

This is where things got fuzzy for me because OkCupid was asking me to define my desires in their terms. I could choose between a few options: new friends, long distance pen pals, casual sex, long term dating, short term dating, and activity partners.

I didn't want to meet any new friends on the Internet, and the last time I even thought about a long distance pen pal was when I was in fourth grade, asking the Guatemalan kid to whom I'd been assigned how to say important things in Spanish. She told me how to say "dinosaur", though I'd been hoping for productive phrases like "Eres muy guapo" so that I could woo cute boys.

People who say they are interested in pursuing casual sex are bold, and props to them for being forward; there is no worse feeling than being conned into casual sex under the guise of it possessing some sliver of hope for something real. I was pretty sure I was not a casual sex girl, but I'd also never dated in New York City or been 22. (This is when the ominous music indicating corruption comes in.) And what the fuck was an activity partner? Was it someone who, like, you agree to go rock climbing with?

I knew that I would have to say I was looking for long-term dating and short-term dating, even though the term "short-term dating" baffled me; did that mean there was an expiration date? Like, "It's been a fun two months, but sorry, babe, it's the 28th and we only agreed to go short-term." I feared that saying only "long-term dating" would make it look like I wanted to get pregnant tomorrow, so I went with the two to balance things out.

4. What are my thoughts on sex?

The one thing that makes online dating slightly different from going to bar is that you talk about sex. You have to answer the questions about sex, or else you look like a prude. Even before I began my epic journey into the battlefield of Internet romance, I knew that was true. But there’s definitely something odd about sitting across the table from someone you barely know over your first gin and tonic and thinking, "Why yes, I know you’ve had sex with as many people as your age divided by two, you like spanking, and you would laugh at me if I farted during oral sex." (All of these are real questions, by the way.)

It’s important to answer honestly — you don’t want to get matched up with someone who believes that women are compelled to give blow jobs on date number two by some higher order of misogyny, but there is one question that it’s OK to lie about. When do you have sex? The options here are so confining. One to two dates, and you sound easy, six or more dates and you sound like the Virgin Mary. Three to five dates is probably the best answer, but it does make it sound like you’re counting. What date is this? The fourth date? Okay, it’s been three to five, let’s go bone!

But then the scary thought hit me: Would I met anyone who I’d even want to see — or worse yet —want to see me — three to five times?

5. What now?

My inbox started to flood with some real gems.

Want to karaookeee?

I like pickles.

Heyyyy shOrtYYYYy.

It was just like a bar, only much more hilarious. Sitting back in my sweatpants and blasting Alanis Morissette, I was able to find the humor in this. At a bar, I might have gone home in tears, and I would have never had the benefit of knowing what was written in alternating caps or not.

But there was one thing that I was beginning to see: I was going to have to dig through a lot of crap before I got to even some shiny crap. This was going to require some effort.