Tag Archives: nyc

The Most Awkward Hello

Over the past few years, I have spoken and written all about my horrendous dating life. Sure, there were a few dates that didn’t leave me crying on the E train, but those aren’t that fun to tell, right? No one asks “How was your date last night?” in hopes that you say, “Fantastic! I think I found the one!” No. They want to hear about the uncomfortable small talk, the crazy stories, and the awkward hello.

Through my dating experiences, I have entertained numerous friends and some employees at 16 Handles with some of the wildest stories from my past, but no story quite got the reaction like the one I am about to share.

This “encounter” as I will refer to it, happened almost six months ago and I am just now ready to publically put it out there, on the internet, forever.

I am no stranger to self-deprecation or embarrassment for a laugh (I shit my pants and wrote about it, remember?) so there should be no reason why this particular encounter should be any different. But it was. And is. This is by far one of the most uncomfortable and awkward moments of my life, but I think I am finally ready to share it with all of you.

January 2014 was horrible. The cold, the snow, and the disappearance of Christmas cookies from my pantry. Saying I was depressed is an understatement.

Luckily, I had that Grindr app running all day, every day, desperate for someone to chat with, and maybe – just maybe –  someone to cuddle with my through the night. (Side note: There is no cool way of asking a total stranger to come to your apartment to sleep next to each other like you’re old buddies from college.) But I digress.

One chilly January evening I was scrolling through the nearby men when I received a message from a profile located 200 feet away. Now, in New York City, 200 feet is nothing, but in Jersey where I live, 200 feet is exciting and unheard of. He didn’t have a picture, but I took the chance and responded.

I responded to his “Wut up?” with a “Nothin’ much, you?” which of course led to “Horny” as many Grindr conversations do. Now, I was in a conundrum. Do I take the bait and say “Me too” or do I simply ignore his chivalrous gesture and keep looking for my next cuddle buddy. I decided that since I did have the apartment to myself that night, and hell, I could be horny if I wanted to be, I wrote back, “Same. Into?” just to get a glimpse of the activities I could be partaking in that evening. I had a heavy dinner and was not in the mood for anything wild or crazy, just a simple and easy hook-up.

Four minutes later he responded with “Just jacking off.”

Ok, I could handle that. I do it alone, why not do it in the company of a stranger. At this point in conversation, I had still yet to see a photo of him, and that’s rule number one of online hookups. I asked if he could share a few pictures and that I would do the same. He sent me two mirror-selfies where he was wearing jeans, a sweater with a gold chain and a fitted Yankee hat. I don’t even need to tell you that, yes, he was Puerto Rican.

I obliged his request to mutually masturbate and sent him my location. Not a minute later, I heard my apartment buzzer ring, signaling my visitor had arrived. I went downstairs to greet him, thinking that was the polite thing to do.

I opened the door and, to my surprise, he looked nothing like his pictures. We’ve all been there, right? Meeting someone on-line, you need to prepare yourself that they may not look exactly like the pictures they sent you. Because in real life, there is no air brushing effect, Instagram filters or flattering angles to make you look skinny.

Saying he was fat would be extremely mean and hurtful. But saying he was thin would be extremely untruthful and deceitful. He was wearing scrubs, so I asked if he worked at the medical building across the street, because that would explain his proximity of 200 feet away and his wardrobe. But he just shook his head no and said he worked in another town and was just passing through.

He was already beginning this relationship with a lie.

We walked up to my apartment, went into my bedroom, and sat on my bed. I wish I could be one of those guys who takes charge the minute we enter the love lounge (this is what I nicknamed my bedroom). Possibly the worst part of a hookup, other than the minutes after fruition, are the minutes prior to foreplay. You want to get naked and they want to get naked, but at the same time, we have to act like normal adults with parents who loved us and treated us well. I never want to just attack them in fear that I may make them uncomfortable.So we sat. And talked.

I heard stories about his childhood, his recent trip to Puerto Rico, and how he dislikes his sister’s new fiancé. I told him about my food blog and how I rarely ever hook up with someone. “I never do this,” I lied as he inched his way closer, rubbing my feet.

Once someone makes the first move, that’s when I go in for the kill. I took off my shirt, got on top of him, and pressed my lips to his, to which he pulled away and said, “I don’t kiss, bro.”

Apparently that’s a thing.

I accommodated his request and started undressing him, throwing his XXL hoodie onto my bedroom floor. Once the clothes were off and the jerking off began, I started to get bored. No kissing and basically no touching. We were just jerking off next to each other, not a sound to be heard.

“Want me to turn on Pandora?” I asked, reaching for my laptop.

“No, but get on top of me.”

I shut the lid to my Macbook and climbed on top of him, successfully mounting myself on the third try. We were now face to face so I leaned in, forgetting his ‘no kissing’ rule. He didn’t forget though, and instructed me to turn around so he could see my ass.

“My ass?” I thought. I wasn’t prepared for that. Showing someone my ass, and in that position, is a treat I save for special people in my life: a boyfriend, someone who buys me dinner, and my pediatrician. Not some random guy! But, remembering my New Year’s Resolution of saying “yes” that I made just a few weeks ago, I turned around so that my ass was inches from his face.

Continuing to jerk off both him and I at the same time – an extremely difficult feat – I could feel both of his hands grab my ass and this is when the spanking began. Not once. Not twice. Not even three times. He just started smacking my ass with his right hand for about 2 minutes straight.

“Ya got it?” I asked as I turned around. He kindly got the hint that I did not to be hit repeatedly, so he tried of one his other techniques. Still with both hands firm on my ass, he leaned in, placed his nose between my cheeks, and inhaled.

Sorry if I lost anybody after that last sentence. I know some of you are reading this on your lunch break or morning commute and I do apologize.

Upon hearing the sound of his exaggerated breath, I shot straight up like Scooby Doo. “Huuuuuhhhh?!”

Maybe it was an accident, I assured myself. This can’t be a thing guys do. It’s fine. It was a mistake. It won’t happen ag—SNIIIIIFF. This time, an even longer inhale from the first. This was no fluke. This guy was literally and figuratively smelling my asshole. After about another 7 or 8 deep breaths, he came up for air, turned me around, and decided NOW he was in the mood to make out.

“I don’t think so, pal” I said, as I pulled my head back as far away from his nostrils.

“What’s the matter? You wanted to kiss before man.”

“Yes, but that was before you stuck your nose into the crevice of my ass and sniffed around like a police dog.”

Needless to say, I laid back down and we jerked off, side by side until he was finished. For some reason, though, I just couldn’t get off.

I handed him a towel and threw him his scrubs and sweatshirt and said I had an early meeting the next day.

“But it’s a Saturday…” he said, confused.

Once he finally dressed, I walked him to the front door, held out my hand and said, “’Twas nice to meet you.” He gave me a handshake that resembled something from the movie “Friday After Next” and walked down the stairs. Feeling disgusting and violated, I ran to my bathroom, turned on the shower to the most scalding water temperature, and got in. I sat there, on the floor of the shower, cradling my knees and rocking back and forth. I felt used, I felt desecrated, and I felt like a container of Vix Vapor Rub.

After thirty minutes of sobbing in the shower, I got out, threw away my sheets, and went to bed.

The following week, some friends and I went out for Happy Hour and the subject of “weird sex” came up. For the first time ever, I stayed quiet and let the other people at the table share their most unusual story. Because we took an oath that night, I am forbidden of re-telling their stories, but after each one went, I felt comfortable enough to open about my recent encounter, hoping that once I told it, they would assure me it has happened to them. Or at least someone they knew.

Nope. This was the first time they had ever heard of this fetish, and now I was mortified, humiliated, and thirsty for another cosmopolitan. I tried to laugh it off, saying I was just kidding and that I made it up so they wouldn’t feel so bad about theirs, but they weren’t buying it.

Five months later, the brutal New York weather had finally subsided and the climate was warm and sunny. I was no longer gloomy or depressed and spent most of my afternoons out with friends or walking around my neighborhood.

One evening, I was coming back from the gym and passed a Dunkin’ Donuts. Deciding to treat myself for having the courage of canceling my membership, I stopped in to grab a few Boston Creams and a Hazelnut Coffee Coolata. Standing in line, I started perusing the other seasonal donuts on display when the person in front of me turned around and locked eyes with me. It was him: The Sniffer.

He looked at me for a few seconds; I suppose trying to remember how he knew me. But I knew. I remembered. I never forget a nose.

I simply smiled and uttered the most awkward hello possible. He nodded his head and turned back around, hopefully just as embarrassed as I was.  Too uncomfortable to stay, I silently backed up and walked out of the Dunkin Donuts, empty handed, with a growling stomach and the smell of regret.

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Love & Other Drugs

A few days ago I had a dentist appointment on 50th and Madison to refill a cavity. While waiting for the dentist to see me, I did what all single gay men do when they have time to kill, I opened Grindr. It’s always exciting going on Grindr in a new area and see different guys, so while I was browsing, this one profile struck me out of all the others. His picture was of him sitting on a boat wearing a life preserver, and I thought that was cute.

So I sent the first message: “You sure know how to make life vests look good.” Ok, I know. Not my best work, but it ended up gaining a response, to which he said, “Let me know if you ever need rescuing.”

A quick and clever reply? Don’t mind if I do. So I took the bait and ran with it.

We ended up chatting for the rest of the day which eventually turned into exchanging phone numbers which ultimately turned into setting up a date. Our original plan was to meet up on Saturday night for a few drinks, but yesterday while sitting at my desk I had the sudden urge to be a little crazy and go out on a school night.

“Hey, would you be free to meet up for a bit tonight?” I asked, hoping he didn’t already have preset plans.

“I’m free after 8 – let’s do it!”

Perfect, I thought. I could go home, cook dinner, shower, and trim my pubic hair. He also told me that if things “went well” I could just crash at his place that night. So, just to be prepared, I brought my office key, phone charger, and toothbrush with me, all hidden in various jacket pockets. “Of course things are going to go well”, I thought. “I’m gonna get my groooove on tonight!”

We decided to meet up at a loungy gay bar in Hell’s Kitchen at 8:45. I, the one who lives in New Jersey, arrived on time while he, the one who actually lives 4 blocks away from said bar was 15 minutes late. Uncomfortable with going in the bar  alone, I stood outside and chain smoked until he arrived.

On first impression, I was satisfied. He was handsome, had a nice smile and a beautiful head of hair. (I have noticed since losing my own hair how much I value a good head of hair on someone else.) He stood with me outside while I finished my cigarette and we started some small talk. I still had my headphones in and he said that he loves having his headphones in so homeless people don’t bother him. I told him I like leaving mine in so I can walk down the street talking to myself and people think I’m on the phone, having a fight with the cable company. (Don’t ask what I talk to myself about).

We went in and sat at the bar and ordered our drinks. Him, a Stella and me a Coors Light because I am the epitome of class. Plus, it was a Thursday night, I didn’t want to get wasted.

The conversation never really had a great flow; lots of awkward silences and “Oh, I like this song” comments. After we both had two beers, we decided to switch it up and have something a little stronger. “Maybe if we get a little tipsy the conversation will be better” I thought to myself.

Nope. Unless “better” is passive-aggressively making snide comments to each other.

He asked about my writing and I told him about that book I wrote. “It’s a book about the way technology has influenced the way people meet and fall in love, with some personal stories thrown in.”

“That sounds boring.”

“Oh.” I said. I was waiting for a ‘just kidding handsome’ with a light leg tap, but it never came. So I continued, “Well, I don’t think it’s boring at all! I mean, I am biased, but it’s really funny and smart and I think people would get a kick out of hearing some of my horrible dating stories.”

“Define horrible.”

I hate when people ask me what my worst dating story is because I’ve had some bad ones, but honestly nothing so bad or disturbing. “Well,” I answered, “I once went on a date with a guy who was doing cocaine the entire time in the bathroom. That was pretty bad.”

“Did you do cocaine with him?” he asked.

“No! That’s insane.”

“To you it’s insane. To people who live in North Dakota it’s insane. But imagine people living in NYC or San Francisco reading your book. You think they are going to read that and find it interesting or extreme? Absolutely not. You should have done the coke with him. You should go to circuit parties and pop Molly. You should seek out threesomes and orgies and leather parties. You should immerse yourself in the culture. Then, you will have one hell of a book.”

Uh.

At this point I was losing the remaining interest I had in him and excused myself to go to the bathroom to text my friend the thumbs-down emoji.

When I returned, he was chatting with the guy on the other side of him and eating the mixed nuts from the bowl in front of him. Finally, after two minutes of me sitting there, he returned his attention to me.

I quickly tried to change the subject to something – anything – else. I did see his point, and I do agree that sometimes I am a little vanilla and prudish, but at the end of the day, I am not trying to write a book about how outrageous and slutty one can be. My ultimate goal is to write a book about how pathetic and desperate one can be.

I saw that my drink was pretty much full and it was getting past my bedtime and the idea of going back to his place was slimmer than my waistline in 2011. (I used to be really skinny). So I started taking huge long gulps of my drink, hoping to end this date as soon as possible. And this is about the time when we got on the topic of judging a book by its cover, metaphorically speaking.

He went on to tell me how he can pretty much know everything about a person within the first three minutes of meeting them. I, too, somewhat agree with this ability. Maybe not as short as three minutes, but I can usually tell very soon if I will like the person or not –  but I wont know everything about them.

Curious, I asked him what his take on me was and he shied away and asked, “Do you really want to know?”

I took one long drink of my vodka and said that I would love to know his first impression on me. I mean, one of the best things about going on dates with people is you get to learn things about yourself that maybe no one else could have showed you. So, yes. I wanted to hear what this stranger thought about me.

“Well,” he began, “you seem very reserved and a little uptight.”

Ok sure, I can definitely see that. He is not the first person to call me uptight. I know I am. Fine. Whatever. Next. 

“Ok, I agree. And?”

“And you seem very set in your ways, not wanting to change or shake things up. I feel that your favorite time of the day is when you can lay in bed and play candy crush and fall asleep by 10pm.”

Wow, he really was hitting the nail on the head. That IS my favorite time of day. But so what? Who cares?

“I agree with that assumption as well. Anything else?”

“I feel that NYC has made you tired and cynical. And you don’t trust people easily.”

I nodded my head and said, “Well, I do believe NYC has made me somewhat cynical, but I have been here for a few years and you only just moved here 2 months ago. So it is a bit different. You are still excited about the city and want to go out every night and explore. That’s how I was when I first moved here. But I guess things changed.”

I then thought about how he said I don’t trust people easily. I feel that I am pretty open with people, and I think my big issue is that I trust and let people in way too much and too easily. So I asked him about what I have done to make him think I am a closed-off person and he replied, “Because you are wearing an undershirt.”

Wait, what?

“Wait, what?” I was so confused! “What does an undershirt have to do with anything?”

“Well, I took a Psych class back in San Diego and my professor said that the number of layers people wear indirectly affects the number of layers they have for letting people in. It’s like a wall. I’m just saying the minute I saw you were wearing an undershirt, I kind of knew you were going to be uptight and reserved.”

At this point, I had no idea what to say, and these drinks were hitting me all at once and I felt that I needed to just pass out. I told him that I was wearing an undershirt because it was 18 degrees outside and I had to walk 10 blocks to get to the bar and then I made a snarky remark about how he shouldn’t let some teacher at a California Community College influence the way he reads people.

 

Needless to say, we both paid our check and headed out into the blistering cold weather – although I wasn’t too cold because I had my good ole undershirt on me.

We said good-bye with the promise of hanging out again soon, I hugged him and went on my way back to New Jersey.

While going through the tunnel on the bus, I suddenly got very lightheaded and felt like I was going to faint. I looked out my window and felt like I was in a rocket going into space and started tweaking out. I needed to get off this bus immediately, I thought. I tried focusing on anything but my mind was going a mile a minute and I couldn’t concentrate on anything.

Once off the bus, I ran home (fell twice) and jumped right into my bed with the lights off. Hoping I could just pass out, I realized this wasn’t going to be that easy. I was having a case of the ‘spins’ and no matter which side I laid on, I felt like I was going to throw up. Which I eventually did. I ran to the bathroom and spent the better part of my evening throwing up beer, vodka, and Hot Pockets.

A few hours later, when I was finally done being sick, I sat there on my bathroom floor and pondered about how I got this drunk from three drinks – two of them being Coors Light.

The only thing that was going on in my head was “I got roofied.”

I had heard of people using a date-rape drug and always wondered what it actually did to the person. I was wondering to myself that if he did, indeed, slip me a date-rape drug, why didn’t he date-rape me? Did he have a change of heart? Did he no longer want to rape me? I was all of a sudden so upset and ashamed. I sat on the cold bathroom tiles and thought “am I not date-rape-able?”

I then quickly changed my thinking. “There is no way he drugged me! No one does that anymore. I’m sure I just drank more than I thought.”

The next morning I woke up, took a nice long shower and went to work. Upon re-telling this story to my co-workers, friends, and the guy at the bagel shop downstairs, I came to the conclusion that I very well may have been drugged. “I did leave my drink to go to the bathroom!” I said, feeling enlightened.

I decided to send him a text message to find out the truth before I just start making false assumptions. So I wrote:

“Hey! Hope your morning is going well. I just had a quick question… Did you put something in my drink last night?”

To which he responded, “NOW you have your story!”

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The 15 Worst Things I Have Heard on a First Date

Dating is an incredibly difficult and tiresome activity us 20-somethings need to partake in. Here is a compiled list of the 15 worst things  I have heard on my many dates. Enjoy. And may you never ever date these people.

1. “I’ve actually never read a book in my life.” 

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2. “I just did a line of coke in the bathroom.” 

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3. “Are you going to eat all of that?”

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4. “Oh, I actually still live at home.”

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5. “Mind if we stop at the cemetery real quick? I need to drop something off on my father’s grave.” 

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6. “Can you order me a Malibu Bay Breeze?” 

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7. “Is the shaved head a look? Or are you going through chemo?”

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8. “You Look Different in Person.”

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9. “I forgot my wallet. Can you spot me?”

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10. “Want to skip dessert and head to my place?”

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11. “Really? It doesn’t look like you have a gym membership…”

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12. “I quit my job on Wall St. My biggest passion is club promotion.”

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13. “Wanna fool around in the bathroom?”

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14. “Don’t you know how fattening Macaroni & Cheese is?” 

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15. “I think I’m falling in love with you.” 

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I guess it is safe to say I will be single for a long time. It’s fine. I don’t even care! 

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