To ignore Craigslist’s ‘Misc Romance’ section would be like looking at a Magic Eye photograph only to never see the sailboat or clown hidden within the rose petals or rocking chairs. Living off Craigslist without personally experiencing the most controversial and anonymous section of the site is wrong, almost as wrong as deceiving a person that you are in fact looking for a relationship or sexual encounter.

But because I am a morally corrupt individual and peeling the layers off Craigslist is far more important than my eternal damnation, I decided to ask the elephant in the room out for a date.

Craigslist has several ‘Personal’ sections, nine to be exact, ranging from ‘Strictly Platonic’ to ‘Casual Encounters.’ Seeing, however, as my use of this section is strictly for research purposes, I decided to stick to the least sexually driven section of the site, ‘Misc Romance.’

My housemate Sam has a bit more experience than I using the site to find friendships and relationships, and describes the listings on ‘Misc Romance’ to be “so homely.” They are looking for long-term relationships and real connections, a striking contrast from the no-strings-attached (NSA) users on other sections.

I wanted to find out what it feels like to go on a date off Craigslist—to feel the pressures involved in online dating and learn how to court using the site. But Craigslist, as I have learned with other social sections, largely plays to a gay populace. The number of ‘Women seeking Men’ is underwhelming, and so I decided to have a man date.

Before ever responding to an ad, I asked one of my best friends Steve, who also has a fair amount of Craigslist experience, for advice.

Steve told me I could direct the date the way I wanted. “The good thing is, there isn’t going to be any pressure,” he told me over video chat from his Chicago apartment. “It’s the first date, you wont have to do any PDA.”

But I had a lot more to worry about than PDA, like my status as a “gay male,” which I am not. Something I never considered were questions about my sexuality. “You need to be prepared to answer questions about your out status,” he told me.

Steve and I decided it would be best to identify myself as a semi-out gay man. My story: I have told some close friends, but not everyone.

I want to take a step back. Before embarking on this section of the experiment, I thought a great deal about the implications of my actions. Am I harming the Craigslist community by going on an undercover date? Will my girlfriend be accepting of my need to gather a full picture of Craigslist? Am I going to hurt the person I go on a date with?

After responding to a few listings, mostly low key, “Let’s grab a drink and see how it goes,” I settled on a guy who was around my age and wasn’t looking for anything beyond a “relationship.”

Still, I found myself struggling with my moral compass. My housemate, Sam chimed in on my debate telling me I had better show him a good time, not treating him like a lab rat.  He worried that I could hurt the sexually shy person who agreed on the Sunday afternoon date.  Steve said similar things, instructing me to “Just be [myself].”

The encounter was not going to be anything serious but I still couldn’t treat my “date” as a subject. “Look into his eyes,” Steve told me.  “If you want to play it like you are interested, really pretend you are interested.”

Originally, my date and I agreed to go bowling, a very low-key, public activity. But because I was still recovering from my snowboarding bruises, and because I was told the less date-like the better, we changed our plans to just meet for a drink.

Well, I wrote that a few weeks ago. My date has since bailed and I have gone searching for a new person to experience the Craigstlist dating world. Steve told me it is not out of the ordinary to have someone flake out on you. So I put the ball in Craigslist’s court. I listed myself.

My post was simple, describing my body type and hobbies—I tried mimicking the low-key ads I have seen and after some vetting, I settled on a 26-year-old guy who seemed non-threatening.

We agreed to meet for a drink at a local brewery, play some pool and decide if we “hit it off.”

We didn’t.

Evan, we shall call him, is not the type of person I would even consider as a friend. He is unemployed— it doesn’t appear like he is looking either—not interested in things I enjoy and seems to be in a perpetual state of inebriation. I had a difficulty directing the conversation from his “love-to-party” mindset and was as ready to leave as quickly as I had come. But I didn’t go on the date to meet someone. I went as a means of self-reflection at the hands of Craigslist.

Honestly, I held Craigslist to a high esteem. I imagined a simple way to meet the right person. Now I can’t say I have a great deal of experience, but dating on Craigslist is just as difficult as any of the other alternatives. It requires diligence, thick skin and willingness to meet a lot of creeps. Before ever going on my man date, I was turned down, ignored and given the run around from several different listers and responders.

At the bar today Evan and I played pool. It was clear to me that he must have had a few drinks before he arrived as he was already slurring his speech and making a fool of himself. Occasionally he would brush by me and engage in the PDA I was promised wouldn’t come with a first date.

I consider the whole thing quite harmless and was never so uncomfortable as to feel the need to run out the front door, though I really wanted a decent experience. Wanting to end the “date” as soon as possible, I agreed to drive him to his next bar—he had plans to drink unlimited suds for the remainder of the afternoon for $8. I dropped him off at the front of the bar where, luckily, a large entourage scared him from making a move, though he did grab my face awkwardly.

As the car door slammed, I exhaled deeply. We didn’t discuss any of the things I was prepared for. My status and interests were irrelevant and I ran out of questions after the second game of pool. The conversation was mainly Evan-centric and I really only wanted the whole thing to end.

Moral of the story: Craigslist or not, dating sucks.

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