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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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Sweet, Sweet Revenge

Everyone loves a story about revenge, right? While this story may not deal with violence or cunning intelligence, it does deal with lies and deception. And, well, a little bit of humor. Enjoy! 

Early in my second year at FAU, I had lost half of the freshmen fifteen, I was attempting to go to class, and I had fully broken up with Jon. And clearly by “breaking up with”, I mean changing my phone number and deleting him off of Myspace.

Remember those days before Facebook was the powerhouse it is today and Myspace was well, stupid? The days when we still had both accounts open, friended the same people, posted the same pictures, and left the same comments on our friends walls. Boy, were we all idiots.

Anyways, I had realized that the last thing I wanted was a relationship. I was in my prime, in a new city, and I was tired of being tied down. Well, relationship speaking. I was definitely not opposed to a little S&M bondage (just don’t tell my life insurance carrier).

I wanted to go out and have as much fun as I possibly could. I was a nineteen year old college student with a fake I.D living in South Florida.

My fake I.D. was actually a driver’s license I stole out of somebody’s wallet at a dorm party and replaced with a Coldstone Card. While I was eligible to gain access to all of Miami’s hottest clubs, they were eligible for a free ice cream cone. Even Steven.

One November evening, I went out for my 20th birthday with some friends to a bar in “Downtown” Boca Raton. I say downtown in quotes, because anyone who has ever been to Boca knows there is no downtown area. It’s just the place in town without a bagel shop or Synagogue.

I was accompanied by my closest friends, Cory, Marissa, Katie, Jamie, and Josh and I was already a little drunk from my two glasses of wine from the Cheesecake Factory.

“I am so happy that you all came out to celebrate my birthday” I exclaimed after the each bought me a birthday shot. In another world, I would have preferred five totally different people, but I made due.

“Let’s do Lemon drop shots next” Cory shouted over the 80’s cover band.

“Let’s kill ourselves” I shot back as I readjusted the birthday crown I bought for myself earlier that day at Party City.

In addition to the crown, I was donning a shirt Marissa had bought me to wear for the night. It was neon green that had “Made in the Eighties” written on it.

“You know, because we are going to see an 80’s cover band tonight, and well, you were made in the eighties. Get it? It’s like…a double meaning!”

Man, I need new friends I thought as I graciously accepted the shirt and wished that people would have stuck to the list I handed out weeks prior. Aside from the fun 80’s shirt, I got a “Friends” desk calendar from Josh, an empty picture frame from Cory, and a bottle of champagne from Katie and Jamie. I was most excited about the champagne until they drank it before we went out to dinner. So, my real gift from them was an Andre sticker with a matching cork.

We spent the rest of the evening dancing to the hits of Billy Idol and Hughie Lewis and the news, all while drinking overpriced beers.

During, the bands rendition of “I Wanna Dance With Somebody”, I realized that I, too, wanted to dance with somebody, anybody but my friends. I turned to my left and saw two overweight forty year old women in matching Madonna costumes. “Eh” I thought. I then turned to my right and saw a group of fun people, my age, dancing and having the time of their lives. Since I was drunk, and when I’m drunk, I feel invincible enough to do anything, I jumped in the middle of their dance party.

Usually, they would have pushed me aside, or walked away, but seeing as I had on my “Birthday Crown”, they all embraced me as if I were one of their own.

After fifteen minutes of non-stop dancing, the one boy in the group turned to me and said “Sweet shirt man. I totally get it.” I faked a laugh because he was cute. “I’m Tim”.

“James. Nice to meet you.”

“So, is this how Boca is every night?” he asked while wiping the sweat from his forehead.

“Not really. Boca kind of sucks. Do you live in West Palm or something?”

“Pittsburgh, actually.”

“Are you that big of a fan of The Breakfast Klub that you traveled all the way down here to watch them play Whitney Houston to death?” (I know, too soon).

“No, I am actually here visiting the FAU campus. I’m thinking about coming here next year, so I wanted to check it out” he responded.

“Oh, awesome!” I shouted over the music. “You will love it, it’s a great school.”

We spent the remainder of the evening drinking, and dancing, and getting to know one another. You know, like you do at an 80’s cover band party. When the end of the night came, we exchanged phone numbers and added one another to our Facebook pages, as one does nowadays. I headed home and couldn’t wait to turn on my laptop and browse through his 453 pictures.

The next few months, Tim and I had a pretty sporadic relationship. One week we would talk every day, and one week I wouldn’t hear from him. It isn’t uncommon behavior with someone who lives 1,500 miles away. I still went on dates, and I am sure he sat at home crying that he wasn’t with me. Everything was still normal.

After having a really good month – meaning we sent over a 30 text messages to each other a day and talked on the phone every night – I decided that I didn’t want to wait until fall to see him, so I finished up my glass of vodka and called up Tim.

“Hey Jimmy-Jam, what it do in the Florida South?”

“Hey, Tim. I am just sitting here on my porch, smoking a cigarette, and I decided that we should plan to see each other. I mean, I know you are moving down here in the fall, but it would be nice to see you beforehand. Don’t you agree? I think we should arrange something. ” I couldn’t believe I was rambling on so much about wanting to see him. I also couldn’t believe I could finish an entire bottle of Smirnoff Vanilla vodka in one sitting.

“I feel ya, holmes. Well, I mean, I don’t have anything going on up here. Would you want to come to Pittsburgh and chill for a weekend?”

Would I?! Wait…Would I? I didn’t know anything about Pittsburgh. I didn’t even know what state Pittsburgh was in, but I knew I was in the state of complete determination and desperation to not have to care about that.

“I would love to come visit you in Pittsburgh! I’ll check out flights tomorrow and let you know!”

We hung up the phone and I logged in to my Delta account to search for flights. The next morning, I informed Cory and his boyfriend about my travel plans.

“Wait, wait, wait. You’re going to fly up to Pittsburgh? To see that guy you met on your birthday? Seriously?”

“Yes, Cory. Some of us have a spontaneous side. You should try it.”

“Spontaneous is about driving to the movie theater and then deciding what to go see, or trying something different at Denny’s. Not flying across the country for some guy. What you’re doing is crazy.”

“First of all, it is not crazy! And secondly, we go to Denny’s every week and every week you order Moons Over My Hammy, so zip it. What do you think Mauricio?”

“Yo no se.” (Mauricio is Peruvian and doesn’t speak much Enlgish.)

“Ugh, you are just jealous of my happiness. Both of you! I’m buying the plane ticket and I’m going up there. I’ve never been. Plus it would be nice to eat a cheese stake and see the Liberty Bell.”

“The Liberty bell is nowhere near Pittsburgh!”

“Whatever!” I stormed out of the living room and sat at my desk and bought my plane ticket for the weekend in two weeks. That should give him enough time to get everything ready and plan all of our fun activities and for me to get enough time to take off work. Perfect.

As soon as I received the e-mail confirmation of my flight, I texted Tim the details. His text was brief, but he definitely sounded excited.

Two weeks later, I was sitting in my living room watching When Harry Met Sally when Cory sat down beside me with a bowl of popcorn.

“You all packed?”

“Yeah, I think so. I hope it isn’t too cold up there this time of year, I don’t have any winter jackets.”

“It’s March, you’ll be fine.” We both took a scoop of popcorn.

When the movie finished, I headed off to bed. I wanted to have a good night sleep for my big day. I hate flying, and was trying to mentally prepare myself that the plane would not crash.

I set my alarm for 11:30am, so I would not over sleep. I hopped in the shower and got myself ready while I made Cory bring my bags to the car. I decided to text Tim once I got in the car: “Omw to the airport. See you in a few hours!”

His response was almost immediate: “I don’t think we should go through with this. I am sort of getting back with my ex. Well, we actually never broke up. I’m Sorry! Hope you can get that ticket refunded!”

I sat in the passenger seat of Cory’s Ford Taurus in complete shock. “Turn the car around. I’m not going. And please don’t tell me you were right.”

“Want to go to Denny’s?”

The following weeks were consumed with studying for finals, working at the restaurant to make extra money, and to forget about Tim. I hadn’t spoken to him since his text he sent me en route to the airport, and I didn’t plan to ever again. Well, until I ran into him at that very same bar on my birthday the following year.

“Thank God there is no cover band here tonight.”

“Si” said Mauricio.

I’m going to run to the bar and get some shots of tequila. Who’s in?”

Naturally, everyone rose their hands, so I headed over to the outside bar with Marissa. When the shots were laid out in front of us, the bartender said “That will be 28 dollars.” I looked over to Marissa.

“You heard him, pay the man.”

“I thought you were buying the shots?!”

“It’s my birthday, why the hell would I buy everyone shots? I said I wanted to get shots. Not buy them.”

A very disgruntled and aggravated Marissa helped me carry the eight shot glasses over to our table where everyone shouted “Thanks James!” over the music.

We all toasted to me and my youth and chugged down our shots. I slipped one of the lime wedges into my mouth and looked up, and that is when I saw Tim, standing two tables over with a bunch of girls.

“It’s him” I said.

“Who? Ryan Reynolds?”

“No. Him. Tim.”

I suddenly looked to Cory for advice. I was begging him to tell me what I should do in this situation. Should we all just leave and head to a different bar, or should we stay and act like we are having the time of our lives?”

“But I am having the time of my life!” he exclaimed.

“That’s cute, but I really don’t know what I should do. Screw it. I’m going over there and saying something.”

“Are you sure? What are you going to say?”

“I haven’t decided that yet. I’ll figure it out on the walk over.”

Four steps later, I was standing behind Tim holding a huge Nikkon camera taking pictures of three random girls. Once the shot had been taken, I gently tapped him on the shoulder.

“Hey-oh-my-God-What are you doing here, James?!”

“I live here, remember. I see you are living in Boca now.”

“Yeah, for about a few months. I love it. Hey! We met here exactly one year ago today! How cool!”

Why the hell was he being so nonchalant about everything? Does he not remember what he did? Is he even going to bring it up? Should I even bring it up?

“Awesome. Well, I just wanted to say hi. I’m going to go back to my friends. See ya around.”

“No, no, no. Let me at least buy you a birthday shot. Don’t think I don’t remember!”

Of course, I thought. This he remembers. Being raised right and taught to never say no to free alcohol, I agreed and we headed off to the bar. An hour later, I was hammered and completely forgave him for having a boyfriend and telling me not to come up to visit him the day of my trip. My friends came up to me and told me the bar was closing and that it was time to go, so I hugged Tim, gave him my new cell phone number, and told him to add me on Facebook.

In the parking lot, I was just getting into the back seat of Cory’s car when I heard Tim screaming my name. I looked over and saw him running towards us, waving with one hand, and holding his camera with the other.

“Shit, James. I have a huge favor to ask of you. My credit card got declined at the bar and I have no money to pay my tab. My friends already left and they aren’t answering their cell phones. Any way I can bum fifty bucks?”

Against all of my better judgment, I took off my seatbelt and headed back into the bar with him and paid for his tab on my credit card. Happy Birthday, James. As we walked back out into the parking lot, I said goodbye again and approached the car.

“Wait! I…well, I also don’t have a ride home. Can I just crash with you tonight?”

I looked over at Cory and Mauricio and felt suddenly so alone. It was my birthday and I’ll have sex with an asshole if I want to. I said yes, and we went back to my apartment.

The next morning, I drove him back to his apartment. He kissed me on the cheek and said, “I promise, I will mail you a check for the fifty bucks. You’re a life saver.”

“…But you don’t have my address!” I hollered, but it was too late. He was already in his complex. I drove back to my apartment to take a Benadryl and sleep the day away. I’ll never hear from him again.

_________________________________

Five years later, I was living in New York City trying to make it big as a writer, and barely scraping by as a waiter. I spent all day filling out job applications and sending my resume to every publishing house in the city, and all night serving $18 dollar cheeseburgers in Time Square.

One night after work, I opted out of going to a bar and instead returned to my bite-sized apartment to watch a bunch of YouTube clips and hangout on Facebook. When I logged on, I saw that I had a message. It was from Tim.

“Come on!” I screamed to my computer.

I opened up the message and it read:

Hey James. Long time, huh? Well, anyways, I don’t know if you know this, but I work for a television production company as a PA, and I travel all over the country. Next week, I am going to be in New York City, and I saw that you now live there (way cool) and we are looking for a few extra hands to work with us for a week. If it’s something you would be interested in, let me know. Would be great to see ya!

Tim

p.s. I also need a place to crash.

I stared at my computer screen for a good fifteen minutes before even thinking about what to reply. Instead, I called Cory. He couldn’t believe that Tim had messaged me and said I should definitely fuck with him. “He told you not to come visit him while you were on the way to the airport because he had a boyfriend. He had you pay his bar tab on your birthday. James, it’s revenge time.”

Yes, it totally was revenge time. He was a dick. An asshole. And a horrible lay. This was my chance to get him back. So, I hit the reply button and said:

Hey Tim! It sure has been a long time! A production assistant? That sounds like a fun job. And I love T.V. So I would be very interested in helping out for the week. And don’t worry. You are always welcome to come stay with me. Can’t wait to see you!

 J 🙂

Not five seconds after I sent the e-mail, Tim was texting my phone thanking me for wanting to help out, and for the place to stay. I said it was my pleasure.

The next week, Tim was on his train from Boston to New York and said he would be in the city in about an hour. He texted me when his train got in and asked what address he should give the cab driver. I told him my address was 42 West 88th street, Manhattan, New York.

…I live in Hoboken, New Jersey.


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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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