NYC's 8 Worst Dating Nightmares (Yes, They're True!)

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When it comes to horrible dates, we've all been there, done that...maybe even done it again. And everyone knows the real freaks congregate in NYC, meaning terrible one-on-ones are amplified in the most gruesome way, and often broadcasted across Facebook for all the world to recount. But because we love sharing our deepest innermost feelings and desires with YOU, we've asked you, our Big Apple readers, to submit your worst (albeit best!) dating nightmare stories. As we expected, you far exceeded our expectations. You had us laughing, crying, laughing again, and then almost vomiting. To make sure you're not sweating the prospect of being single forever, we've narrowed down our favorites (or least favorites, depending on how you look at it) to eight tales so truly horrific, you'll be ready to swear off men forever (plus accompanying artwork from The Blake Wright). Okay, that's a lie, but click through to read first-person tales*—from a literal blind date to a Civil War fanatic—that you'll be sharing again and again. Don't blame us if you can't sleep tonight. Or do.

Click through to get in on eight truly horrible dates!

*Names have been changed for anonymity when requested.



Kristen, Upper East Side

"We all know that meeting in NYC can be difficult, and since I have lost count of the numerous people I know that have met on JDate or Match.com, I signed myself up on a dating site. I was seriously looking for a nice, down-to-earth guy that had similar interests and was looking for a nice, normal girl. Isn't everyone? This is an excerpt of an email I sent to all my friends after the date from hell. What a waste of precious time!

Profile: Mr McSteamy
Wants children: Yes
College: Cornell
Works in: Finance
Drinking: Socially
Salary: I'll tell you later
What he wants: 5'0' to 5'9', smart, inquisitive, fun-loving girl to share life with.

"We met at Coffee Shop in Union Square.
Him: 'Hey so tell me about yourself. What would you like to drink? What do you normally drink at brunch?'
Me: 'I normally drink Champagne, but I heard the Mojitos are great here, so I will go with that.'
Him:'I'm on my fourth cup of coffee.'
Me: 'Oh, rough night last night?'
Him:'Yeah. So, what else? What else?'
Me: 'Ummmm.' (He kept saying 'what else' like to hurry the convo or something—it was really weird)
Him:'Ugh, do you know anything? OMG, look behind you, I've been trying to figure out these people since I got here.'
Me: 'Hmm, interesting group. It looks like they are DJs.'
Him: 'So, what else? Where do you go to the gym? I go to NYSC.'
Me:'Sports club L.A. I used to go to NYSC, but I live right next to L.A.'
Him: 'Oh, strippers work out for a discount there, don't they? I guess it makes sense. Get a little work out in, go right to work in your little outfit. What do you think about that?'
Me:'Um about what?' (Honestly...I had to play dumb at this point because I knew this guy was weird.)
Him: 'That life, you know being a stripper, getting a discount in the gym. How cool would it be to work out and go straight to work?'
Me: 'Umm.' (Is this guy really asking me these questions? How am I supposed to respond to this?)
Him: 'So, what else? Your turn!!'
Me: 'Ummm.'
Him: 'I hate moments of silence. So, tell me about reality shows you watch?'
Me: 'Oh I like Bethenny Frankel...I like The Voice!!'
Him: 'Do you watch Idol?'
Me: 'Nah, I like The Voice. It's diff—they don't judge you and the judges don't face the singers.'
Him: 'Should we turn around?'
Me: 'Haha' (eye roll)
Him: 'I'm gonna use the little boys' room. When I come back, it's your turn to ask me questions!'
Me: 'Oh god.' (eye roll...I'm exhausted what is with 'what else'? Why can't he let the conversation just flow?)
Him: 'Okay, whaddya got?'
Me: 'Umm.' (but before I could get a word in....)

Him:'Okay let's do this: What's the capital of Albany? Name three hockey teams in New York. When is the election this year? Who ran against Obama? How was Kennedy killed? Where did Jackie O. go after he was killed? Who killed JFK? Who killed the guy that killed JFK? Name three presidents that were assassinated. Who killed Lincoln? Name four oceans. How tall are you on a good day? How many inches are you? How many ounces are in a liter? In a coke can? What weighs more, 100 pounds of gold or 100 pounds of feathers? If you were a stripper what song would you come out to? How much would you charge for a lap dance? What if it were for your friend? How long would your dance be? If you could make love to a Yankee player who it be? Name five Yankees. Two Mets. What color is a mango? What rhymes with orange? What's 1000-900+200? If you fell off your chair at what velocity would you fall? If you walked down a red carpet what designer would you wear? Why? Name five brands of shoes, no, 10. I made it 10 now. How do you make a Long Island Iced Tea? Screwdriver? What's another name for a rooster? If a train were going 30 miles per hour, how how long would it take to get to Washington, D.C.? Name five malt liquors. Five beers. How much do you have if you gave 13 quarters? If your tab was $299 what would $10.75 tax be? How many in a bakers dozen?'

"That's right. Rapid-fire questions and I answered all of them like a jerk. Some people ask me why I answered all those questions, but sometimes these stupid dates make great stories, so I went along with it. Who has all those questions in their head? According to him, I scored a 60 on my test...a big fat D. I know one day Ashton Kutcher is gonna reveal himself and tell me that my whole dating life is one big Punk'd episode. You just can't make this up! I don't know if this is my best worst date...they are all absolutely horrendous. Only in NYC!"



Lauren, Gramercy Park

"I went on a first date with a guy, we'll call him 'Bobby.' I met Bobby at a dive bar of his choosing, and found him waiting with a beer. When I took a seat next to him and ordered a drink, he sat there without saying a word as I paid. That was the last time he was quiet—for the rest of the date, all he did was talk about his dead parents (how they died, when they died, how he couldn’t be sympathetic to family members because he’s the one who lost the parent, etc.), and how I made more money than him (not that he knew how much money I earn). Now, I have lost a parent, but it's certainly not my first date conversation. After 45 minutes of this, when I politely refused a second drink, he ordered another drink anyway and proceeded to chat my ear off for over an hour, until I finally said that I needed to go and made a dash for the door. He followed me out, and walked with me for several blocks, talking about a website for meat I just had to check out."




Liz, Brooklyn

"Mardi Gras, New York City, 2008—I was on what I'd presumed at the time to be a very nice second date, with a very nice guy I'd met a couple weeks before. We'd been on a respectfully sweet-'n'-romantic first date the weekend before, so I was looking forward to a mature, non-sleazy evening with my mid-thirties, microfinancing gentleman caller (we'll call him 'Steve'). Meeting up at his friend's bar that night, I found Steve already chatting with his buddy. Polite intros were made, and when I turned around to order a drink, buddy casually tossed out, 'Clowned up, lately?' Perplexed, I swiveled back around to the convo. Shrugging his shoulders, Steve mumbled, 'Not since Jan's party a while back—you?' 'Susie had a big ol' jam at so-and-so's the other weekend, got me a 45-minute blow job in the back room.' Buddy beamed, turning to me. 'They had a grope-a-clown there, too, but she had made it with an umbrella and garbage bags—not like the usual cardboard box.' He turned his attention to me—'You ever clown up?' Confused, I murmured a feeble no, at which point Steve took my not-running-and-screaming-from-the-room as a thumbs-up, and proceeded to elaborate for the next hour-and-a-half on his titillating 'clowning' lifestyle: His exotic fishnet inventory ('Hot pink vs. my plain ol' black and nudes'); his recent visit to the Adult Video Awards in Vegas ('My friends are on the show Porno Clown Posse—have you seen it?'); and the finer points of patent-leather platform boots ('They're much more comfortable than you think, am I right?'). My proper Midwestern upbringing (and lack of a decent date in months) kept me numbly agreeing and dancing by his side, and then finally allowing him to walk me home. I watched in dumb terror as his handlebar mustache said he'd had a great night, then briskly planted one straight on the kisser, blurting, 'Very good!' before strutting off into the night. Very bad, indeed."




Julie, Brooklyn

"When I first moved to the city, I decided that I would do something challenging each day. On day two, my challenge was to say hello to someone on the subway. So I’m riding the 6 Train, doing a test run on how I will get to my new job, when a guy walks on the subway and I notice that we have the same journal. He looks nice, attractive, tall (about 6’2'), dark, handsome. Perfect! I make eye-contact and ask him what he writes in his journal, to which he gives me a nice smile and tells me that he journals about people on the subway, writes song lyrics and just doodles. We talk for a few minutes and he asks me to write my email in one of the pages, while he looks away, and when he gets to it, he’ll email me. Very cute and charming. We part ways and I think, ‘Wow that was easy.’

"Fast-forward to a week later when this guy emails me to meet up for a drink. We end up going to Lucky Strike in Soho where he orders a fancy bottle of wine, and proceeds to tell me that he just graduated from Columbia, won an award for ‘entrepreneur of the year,’ and is starting a clothing line. He then continues to tell me about past dating experiences and how his ex-girlfriend gave him 'the gift of dis-satisfaction' because she was so amazing, but how he’s trying to move on...blah blah. We bonded—I too had just finished dating someone—and we continued to talk for about two hours, talking about life, New York, our careers, etc. Finally, I decided drinks needed to wrap up, so we headed out. In my head I thought, 'He’s cute, I’d never date him but I might make-out with him.' But, upon exiting, the guy goes 'Julie, I need to tell you something. I lied about one thing...I don’t go to Columbia,' and I said very casually 'Oh okay, where do you go?' He looked at me and said, 'I’m a sophomore in high school.' I guessed he was about 16-years-old...I almost died! He told me he still would like to be friends, and I quickly said, 'Where the hell does your mom think you are right now?!' To which he replied, 'I told her I was at my high-school basketball game' (!!!). All I could do was laugh and tell him that we very quickly needed to part ways. I then received an email a week later asking if I would be his mentor and how much he admired me, to which I quickly responded that all communication was to be cut off. The end."



Faye, Brooklyn

"About 10 minutes into a blind date, the guy whipped out a book about Wal-Mart and started telling me that it changed his life, and that Sam Walton was his God. I nodded along, asked questions, and told myself that maybe I would learn something interesting about Sam Walton...but I could tell there was something off about this dude. Moments later, he proceeded to go on a seemingly unrelated tangent about how everyone in the world 'has their price.' He told me I had a price. When I asked him what he meant by that, he pointed at a woman sitting at the bar and said, 'That girl has a price. I could get her to go home with me right now if I offered her enough money. Same with you.' After picking up my jaw from the floor, I said a few choice words and left. Total creepazoid."



Monica, East Williamsburg

"It was a dreary evening in Williamsburg when I met a friend of a friend who happened to be a bit player on my favorite childhood TV show, Pete and Pete. We struck up a slightly awkward conversation and agreed to go on a date sometime.

"Over an awfully and unpleasantly forward sushi dinner near St. Mark’s ('Can we go back to your place soon?' 'No.' 'Why not—are you a prude?'), I decided that it couldn’t get any worse and we went outside to smoke a joint. Which was exactly the same moment I saw the flashing lights. We got picked up by the NYPD for criminal marijuana possession. My date tried to impress me by arguing with the cops. I was shocked into stoned silence and didn’t say or do anything, not even when my date started sobbing quietly in the cop car.

"At the precinct where I spent three hours of my life, my date was herded into a man’s holding cell with a few Rastafarians while I sat alone in the women’s cell. My date repeatedly and periodically yelled, 'I know you think this is my fault, but it’s not!' And, 'Hey, are you okay!?' To which I screamed, 'I’m not the one who cried in the cop car,' to general merriment.

"A Judge Judy-like judicial figure dropped the charges, and my date eventually gave up on calling to apologize. Added bonus: I lost my job over this, but gained an excellent worst-date story."

Mary D. Coleman, Lower East Side

"After emailing with Henry on OkCupid for about a week, we decided to meet at Home Sweet Home on Chrystie Street for a date. In my mind, I was stoked for drinks with a hot, bearded, blue-eyed hipster from Long Island City, not someone with delusions about being a reincarnated American Civil War Yankee officer. Yes, that’s right, he showed up in full Civil War garb complete with a pipe and a gruff, antiquated speech pattern. The idea of being 'punked' crossed my mind, but it was clear that Henry, a cute, IT guy by day, was living in an era gone-by, when, as we exited to barhop over to R bar, he paused to light his pipe while cursing the 'blasted wind,' and began to tell a ghost story from the reenacted battlefields.

"And as he said goodbye to me and opened my cab door like a gentlemen, he asked for a second date. 'Tell me the truth, do you want to see me again? I’m sick of only having first dates!' I didn’t really hear from him after that, except for a text telling me that he lost his iPod on the field, to which I replied, 'bummer.'"



Irene Rose, Midtown

"I met him on OkCupid. He seemed great, an engineer, 5'10" with dark brown hair, lives close by, very smart. We talked on the phone and it went very well. He was witty, intelligent, and funny. He invited me to meet him for drinks and asked me for a bar suggestion. Seeing as we are both Yankees fans, I asked him if he'd like to head to a sports bar to watch a game. He agreed, and we planned to meet at Penn Station to the bar together.

"I get there and can't find him anywhere, so I call his phone. Then, I notice a short, disheveled man stumbling about on the street. I think to myself: 'This cannot be my date....' But, sadly, it is. He is 5'6" at best, and sloppy-looking with a gross purple shirt half-tucked into his wrinkled khaki pants. He looks nothing like his pictures. But that wasn't what made this date the most awkward date of my life thus far. He left out one VERY important detail—he's 100% BLIND!

"I decided to be a good sport and stick it out. We walked to a nearby watering hole and took a couple of seats at the bar. The Yankees game was on, but of course he can't see it. There are four other TVs playing four other different games. So, I'm stuck giving him a play-by-play the entire time. He was unsteady on his barstool and his eyes wandered all over the place; I could barely pay attention to our conversation. At first I felt bad—this man has a serious disability that he has to face every day. But after missing his mouth with his chicken finger and spilling a bit of beer on me, I knew this was not the man for me. I felt a little sorry for him, but only a little. After all, I was duped into dating this visually impaired weirdo! He should have prepared me for this!"

We were seated next to one of the bar's bouncers who could not stop laughing. I shot him one of those 'please-don't-make-this-worse-for-me' glances and he thankfully moved to the other side of the bar.

After finishing our chicken fingers and beer, this guy tried to make an inappropriate advance. At first I thought he was trying to hold my hand, but when he reached out he tried to cop a feel of my boob. I was shocked and immediately stopped him and told him I was not interested in him. He did not take this well. He asked what he did wrong and looked genuinely upset. I tried to let him down as easy as possible. After he accepted that I would not be going out with him again, we decided to call it a night and walked out of the venue. Then he asked if I had any friends I could set him up with....I did a 180 and left this blind man in the middle of the street. I never saw him again. But I guess he never saw me at all."