Tag Archives: drunk

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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No Way, Jose

The other night after getting home from the gym (right?) and then cooking myself grilled chicken and broccoli (right?) I looked at the clock and it read 9:06pm. It was Sunday and I had nothing to do. Usually, I enjoy my nights in, especially on a Sunday, but I was off from work the next day and wanted to actually do something!

I had been talking to this guy on Tinder for about 2 weeks on and off, nothing serious, but we have been trying to find a night to grab a drink and hangout.

His name is Jose, and when we first started the communication, he was hilarious! Very witty, used many puns, and seemed to take jokes pretty well. Traits I have found are pretty rare in this city.

Okay, those were his pro’s, but what were his cons you may be asking? Well, for starters, he is in his thirties and unemployed. Which is totally fine! I was unemployed for 8 months last year, so I know how difficult it is finding a job in Manhattan.

He also lives in Harlem with three roommates. Again, not that big of a deal. When you are unemployed, money is tight and having roommates is a perfectly acceptable way of saving.

Lastly, he does drugs.

Not all the time! But, he does it when it’s presented to him and available. Sort of like my milkshake addiction. Honestly, I am not a big fan of people who do any kinds of drugs, but to each his own.

So, he asks me to grab a drink in Hell’s Kitchen and for us to meet at 10:30 outside of Therapy. Of course I get there early, so I just stood outside, minding my own business. I ran into a few friends from a previous job that I hadn’t seen in a while, so I said hello and we caught up. In the midst of our conversation, I felt a tap on my shoulder. Jose.

As awkward as I am, I try to finish the conversation with my friends while greeting Jose. Naturally, it was awkward.

We head inside and walk to the bar. He offers to buy my first round, so I grab a table and wait for him. Once seated, the conversation begins. It’s not bad at first. We play catch up, discuss things in more detail that we have already touched on with Tinder (my job, his job search, his family, etc.) It’s not the best conversation, but I went with it.

After a few rounds of vodka sodas, we started getting a little more loose, and the conversation went from boring to interesting.

He put his drink down, looked and at me and asked, “So, is this shaved head just a look, or are you going through chemo?”

For the first time in my life, I was speechless and had no idea what to do. Do I laugh it off? Do I play the cancer card and (hopefully) get free drinks all night? Unfortunately, my conscience kicked in and I told him that no, I was not going through chemotherapy. “I started to lose my hair a few years ago and this is a pretty easy way to maintain it.”

“Oh, ok. Cool. I don’t mind the shaved head” he responded, “but next time, don’t shave it so close.”


We sat there in silence for a few minutes, which, when on a date, a few minutes of silence seems like days. Finally, he turned his attention from the bartender to me and asked, “How is your ‘writing’ going?” Yes, he did air quotes when he said the word ‘writing’.

He then excused himself to the bathroom, which is when I pulled out my phone and sent the usual “HELP ME” texts to a few of my close friends. When he returned to our cozy table, I put my phone in my pocket and desperately waited for a vibration.

“You’re back,” I said. “So, do you play any sports?”

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

“Oh?” I replied.

“See, here’s the thing,” he said, speaking a mile a minute and scratching his nose. “I wanted to do coke last week, so I called up my guy for a bag. He then talked me into buying five bags at a discounted price, so I agreed.”

“Ah, I guess he really is a ‘drug-dealer’,” I wittily replied to no laugh or response.

“But, I didn’t realize how much cocaine that is. So, all day today, I have been trying to sell it to my friends. I brought them with me, so if you know of anybody, tell them to come here and get some. I’ll give them a cheap price. Unless you want some?”

I kindly rejected his offer and told him that all of my Columbian friends were out of town this weekend. Still annoyed from the ‘cancer comment’, I leaned in and asked him if he thought splurging on drugs was the best way to spend his money while unemployed.

“I do what makes me happy.”


The conversation is now all over the place. He didn’t answer one question I asked and just played on his phone, so I started letting my eyes wander to the people in the bar. I spotted a few twenty-somethings drinking white wine and rolled my eyes. “Well aren’t they classy” I said in my best Connecticut accent.

Hoping this would get some sort of reaction and we could spend the remainder of this date criticizing and making fun of people, he shook his head and said, “Man, why are you so bitter?” To which I replied, “Too many bad dates, I guess.”

I chugged my fourth drink and lie about having to work the next morning. We leave the bar and I pretended that my bus to New Jersey was on 5th avenue so I wouldn’t have to walk down 8th with him.

We had a causal good-bye and he told me “not to get raped on my walk.”


I am hoping he got the hint that I was not interested, because if he asks me to hang out again, my only response will be “No way, Jose!”

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