My Top 3 WORST OKCupid Dates Of ALL TIME.

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Three years ago, before I met the stinky/handsome man I currently share my life with, I was a twenty-year-old artsy fartsy idiot new to the Brooklyn dating scene. And what better way was there to exact my newfound sexual freedom then to date the most horrifying string of men the internet had to offer? NO BETTER WAY, THAT’S WHAT. My dates were sometimes sad, oftentimes hilarious, and always horrifying. So, In honor of Valentine’s Day, I present to you My Top 3  WORST OkCupid dates of ALL TIME.

Yes, these things really happened to me. No, I wasn’t on candid camera.

Yes, I live a ridiculous life.  

3. The Time a Guy Brought His Ex-Girlfriend on Our Date

I met Jack on OkCupid during the winter of 2009. I had just moved to a small apartment in Brooklyn, changed my OKCupid location to my hip new borough, and was eager to hit the town with some pretty, young thing on my arm. Jack fit the bill. He was a 27 year old graphic designer living and working in Manhattan, and I wanted to make him mine. After a two week courting period, during which time I deduced that he wasn’t a Ted Bundy-type, we decided to go on a date. We agreed to meet at Rockefeller Plaza and watch the lighting of the tree.

When the night finally arrived, my heels were high, my hair was big, and my skirt was short. I was feeling hot as I climbed the subway stairs and walked straight into a torrential downpour of biblical proportions. A flash rain storm had hit Manhattan and I didn’t have an umbrella. Looking like a drowned rat, I mourned the loss of my bangin’ hair and smokey eye application and womped my way toward the throng of umbrellaed tourists and New Yorkers waiting before the unlit tree. 

As I approached the crowed, I heard a female voice shout in my direction, “Is that her?!” I flung my head around nervously and spied a small woman with curly black hair quickly moving towards me. “Jack! This is her!” She was yelling over her shoulder. My stomach twisted into a tight knot as the woman ran up to me. “Come on!” She barked, roughly grabbing my wrist and pulling me forward, “We’ve got a good spot over here! You can see the tree really well but if you don’t move now we’re going to lose it!” Feeling slightly concussed and completely confused, I allowed myself to be dragged to the outskirts of the crowd while weakly trying to introduce myself, “Umm…Hi, I’m Izzy. Are you Jack’s friend? Or…?” It was no use.

I saw Jack standing amongst the people, umbrella in hand, shifting uncomfortably from one foot to the other as the two of us approached. “Here you go!” the small woman squawked, letting go of my hand and shoving me towards my date, “I found her!” Jack mumbled, “Thanks Sue…” to the woman while I stared at her, bewildered. “It’s nice to finally meet you, Izzy!” Jack said, snapping my attention back to him, “Oh, um, hello…” I forced a smile and awkwardly shook his hand. Silence. We both laughed uncomfortably at the same time. More silence. Sue pointed at the tree. “Look! I think they’re going to light it soon!!” A million panicky questions ran through my head, “Who the fuck is this woman? She’s obviously Jack’s friend…but why would he bring a friend on our date? He didn’t tell me he was going to bring anyone! Maybe he thought I was a murderer and wanted protection …How do I ask him who she is while she’s standing RIGHT THERE?”

Suddenly, the woman turned to me and stuck her hand out, “I’m Sue, by the way.”

“Uhhh. Nice to meet you.”

The three of us stood side by side in silence while the tree lit up. After gazing at the twinkling christmas lights through the haze of rain for a while, Jack invited me out to a diner so we could “get better acquainted.”  Finally, some alone time, I thought– moments before Sue invited herself along. While we waited for our meals, Jack and Sue talked amicably while I twiddled my thumbs, staring longingly at the exit. The waitress brought or meals and I was a pancake and a half in when Sue blurted out, “Jack and I used to date– but now we’re just friends!” She explained, “Very good friends…” My eyes bored through my sunnyside up eggs while Jack picked up where Sue had left off. “She insisted on meeting you! She’s my wing-woman!” I didn’t know what to say, so I shoveled more breakfast foods into my mouth and prayed for death.

The rest of my evening consisted of Sue making fun of me for not knowing enough about Fraggle Rock for her liking, critiquing my dress and shoe combination, and asking me invasive questions like, “Are you still a virgin?”

Later that night, I received a Facebook friend request from her alongs with a private message which read, “I’ll be checking up on you!”

Needless to say, Jack and I never saw each other again. But worse dates were yet to come…

2. The Time a Guy Made Me Read Original Erotic Fiction in His Bedroom During a Storm 

My date with Stephen started out pretty well. He took me to Brooklyn Superhero Supply Co., bought me a strawberry smoothie, and gave me a scenic tour of Park Slope. When it started raining and he invited me back to his apartment, I agreed. Stephen didn’t give off any highly detectible serial-killer vibes, so I was relatively sure I would exit his apartment unscathed. When the two of us entered his small walkup, I was in good spirits, until I noticed that the living room, kitchen, and second bedroom all looked abandoned. Only Stephen’s room had any furniture or working lights in it, and they only consisted of one hanging, overhead bulb, a mattress on the floor, and a rickety laptop sitting on top of a milk-crate. Stephen could tell that I was apprehensive about fully entering his modest apartment and quickly explained, “Oh! Sorry about this– all my roommates just moved out! I’m here by myself until I can recruit some new ones!”

At this point, any logical young woman would have hightailed it out of that dump, but I was an impressively dense girl with a penchant for danger, so my internal alarm system was all but muted. I followed Stephen into his sad, sparse bedroom and glanced around me with just a touch of worry. Stephen reclined on his mattress and asked for me to join him, but I said no, opting instead to perch on the floor in front of his laptop.

“Oh! You want to see something cool?!” He asked suddenly, jumping up off his bed and turning on his computer screen. “Look! I’m working on a digital art piece. I’m taking a bunch of different songs I love and illustrating them. I’m going to turn my drawings into an e-book!” Stephen clicked open a picture gallery with a mix of digital paintings and original writing. I flipped through the gallery and worked hard to neutralize my expression as I stared at some of the worst MS Paint art I had ever seen. “I painted this one while listening to ‘Brothers on a Hotel Bed’ by Death Cab…” He said, impressed with himself. “Wow.” I replied, at a loss for words. “Here–” Stephen clicked open a poorly done digital painting of a topless woman with text over it, “I wrote this story while listening to Daniel Bedingfield’s ‘If You’re Not the One.’ My e-book is going to include some original fiction, too. I would like…you to read it.”

“Umm, okay…” I replied, beginning to feel more uneasy. Stephen turned and grabbed an itunes remote control off his windowsill before laying back down on his mattress, his eyes never leaving me. I heard him clicking the remote and the opening notes of ‘If You’re Not the One’ crinkled through his busted laptop speakers.

Now, to anyone reading this, I want you to click on THIS LINK before continuing. It leads to a youtube video of ‘If You’re Not the One.’ I want you to listen to this song while you read the rest of this story. I want you to fully understand my horror.

I began reading Stephen’s story while my ears filled with Daniel Bedingfield’s simpering vocals. Two sentences in I realized it was erotic fiction. And when I say erotic, I mean filthy. Toys of every kind were involved, with multiple people getting in on the action. There I was in this stranger’s dilapidated bedroom, sitting on the floor, reading the intimate details of his fantasy bacchanalia, while he studied me like a vulture from his bed. I meekly glanced out the window and noted the storm raging outside. I had to think of a way out.

“What do you think…?” Stephen asked from behind me. My voices croaked in my throat, “Oh…it’s….a good story…”

“You don’t like it?!” He asked, upset, “It’s not finished yet!”

“It’s okay!” I stood up while hastily pulling my purse over my shoulder, “I  have to get going any way!”

“Look at the weather outside!” Stephen argued, “you can’t leave now!”

Eventually I convinced Stephen to let me go with the promise that I would call him to set up a second date. I walked through the rain and wind to the subway, feeling much safer out in the storm then inside his room. Stephen tried to contact me a few more times with no degree of success and then finally moved on. Now, a logical young woman would have learned her lesson at this point, but, as we’ve established, I’m anything but…

1. The Time My Date and I Got Summoned to Court for Trespassing 

Funny enough, out of all the dates on this list, my time spent with Alan was by far the most enjoyable. Alan was a nice person, and we got along well. His biggest problem was that he had lied about his appearance on his OkCupid profile, and he really liked me while I didn’t really like him, which is an awkward situation for anybody.

Alan and I met up for lunch in St. Mark’s and the first thing I noticed about him was that he was older and much larger than his OKCupid profile let on. As we sat down to eat our falafels, he admitted that the pictures on his OKC profile were outdated and apologized, saying that he was too embarrassed to post anything current. It was unfortunate, because while I appreciated his honesty, I knew from the moment I saw him that I wasn’t attracted to him and wouldn’t pursue a relationship with him. Still, we decided to hang out anyway.

Outside of Alan repeatedly insisting that he would win me over, our day together was nice. We decided to end it by taking a leisurely stroll through Central Park and entered the grounds around 11:30pm. Alan kept making me laugh and would follow it up by saying, “See? You think I’m funny! I’m going to get you to say yes to a second date!”

“No, no,” I would reply, “I don’t want to date you, I’m sorry.”

After a while, I got a little tired of him pushing me for a second date and decided to call it a night. Alan offered to walk me to the subway and we began to make our way out of the park when we realized that we were lost. After some searching, around 1:10am, we spotted an exit and began walking toward it.

Suddenly, a police car came barreling toward us, lights flashing and sirens on. Alan and I jumped twenty feet in the air and looked around wildly, trying to see who the police were chasing. The car skidded to a stop in front of us and a police officer got out and shined a flashlight in our faces,  yelling, “Stop walking! Stop walking and face the car! Face the hood of the car!” The two of us instinctively put our hands up in the air and turned to face the cop car. “What are you two doing out here?!” the cop asked, quickly moving the flashlight across both of our faces. “N-nothing!” I stuttered out, “We were on our way out and we got lost!”

“Have either of you been drinking?” The cop asked. “No sir!” we both replied in a panic. The officer didn’t seem to believe us and became agitated. “Then what are you two doing here after curfew? Central Park closes at 1am! Do you two know what time it is? Were you in the park causing trouble after hours?” “No, no, no!” We both insisted, “We were just lost!”

Suddenly, a second police car came speeding towards us and stopped beside the first one. The second officer leaned out of his window and yelled to the first, “What’s going on here!?” The first officer informed him that Alan and I were “trespassing,” and that he was going to summon us to court for breaking park curfew. Then, a THIRD police officer came rolling up in a golf-cart yelling, “Is everything okay over here!?”

I looked around in disbelief. Alan and I were surrounded by 3 police officers, two with lights flashing atop their cars, and all three pointing flashlights at us as if we were members of a drug cartel and not two lost people on a bad date. The first police officer summoned each of us over to where he was standing and issued us both a court summons. “You must appear in court at this date and this time,” He told us, “or else a warrant will be out for your arrest, do you understand?” Alan and I both nodded. Then the police escorted us ten steps to the exit of the park and told us to scram.

Alan and I stood side by side in complete silence, shellshocked by what had just happened. I watched Alan slowly lift the summons to his face to read the cop’s handwriting.

“I’m due to appear in court May 26th, at 12pm,” He said. I glanced down at my own summons and saw the same date written on mine.

“So am I.”

Alan was quiet for a long time before finally turning to me and saying, “Well, then I guess…we’re going on that second date after all.”

5 thoughts on “My Top 3 WORST OKCupid Dates Of ALL TIME.

  1. I just opened an OKC account (but haven’t done anything with it yet) and found your article after Googling “OKCupid tutorial”. Now I may be too horrified to continue. Great memoir, though!

  2. Pingback: THE A.S.S. TALKS BACK AGAIN! - Blogologues Blogologues

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