Tag Archives: hookup

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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Bugs Bunny

Last night I got out of my slump of watching episode after episode of Pretty Little Liars while trying to beat level 46 on Candy Crush and went on a date.

Me? Going on a date? On a school night? Unheard of!

For those of you that don’t know, my New Year’s Resolution this year, aside from quitting smoking, losing weight, and re-growing my hair, was to always say “yes”, especially when it comes to dating. And ordering Mac and Cheese if present on a menu.

So, while I was waiting for my lives on Candy Crush to be replenished on Tuesday night, I went on Grindr to see if anyone wanted to come over and “cuddle”. While no one seemed at all interested, this one guy messaged me and we began talking for a little over a half hour. When I said I needed to go to bed (aka I got more lives) he asked if he could take me to dinner the following night.

Being one who never turns down a free meal, I said yes.

The following day we didn’t really text that much, which I liked! He was very confident and just told me to meet him at the restaurant at 8. The restaurant he chose is actually 2 blocks from my apartment in Jersey, so I was extremely grateful.

This is very out of character for me, because when I am talking to a guy, I like to chat all day, every day, for about two weeks so I can know everything about them: their favorite color, where they grew up, penis size, and favorite Julia Roberts movie. I also like to stalk their Facebook page to see about 350+ pictures of them. But, with this guy, I only saw three pictures. All of his left side. All not smiling.

Again, it’s a free meal, I said to myself.

So I walked to the restaurant and a few blocks away I received a text message from him saying he was sitting at the bar. He’s prompt. I like that. I opened the door to the restaurant and spotted him immediately. Well, I didn’t necessarily spot HIM, I spotted his two front teeth.

The reason why he never sent me any pictures of him smiling was all making sense now. I walked over, gave him an awkward hug, and we were sat at a table. Ok, so he has buckteeth. That’s not the end of the world. I’m not that picky.

I started the conversation about work and explained to him a bit of what I do. When I asked him what he does, he said that he works at a medical office as an assistant, but his real passion is “club promotion.” He then went on a 20 minute tangent about how great that lifestyle is, yet how tiresome and lonely it can be. I just nodded.

Now, I love to joke around, but sometimes I forget that people (especially people who met me 18 minutes ago) do not really understand my dry sense of humor and sarcasm. I forget exactly how this came up, but I made an innocent “I’m addicted to cocaine joke”, as you do on a first date, and it did not go over so well.

I completely forget that he was from Columbia.

So, he responded to my comment and decided to tell me all about his trouble with drugs “in his past” and then proceeded to ask me if I had any lying around my apartment.

All in all, we had an average dinner. I am really good at coming up with things to talk about, so the conversation flowed, from the Yankees to quoting The Devil Wears Prada.

Once the waiter cleared our plates (and brought me my third glass of wine) the next words out of my dates mouth were, “Well, when I was in acting school…”

I quickly chugged the Pinot Noir in front of me and graciously asked for something with tequila. I was going to need to be extremely drunk to hear about monologue workshops.

The date was going longer than I had expected and hoped, and I don’t think I could have yawned or said “Gee, I have to be up early” enough for him to get the point. Finally, he sipped the remaining ounce of his Bud Light that had been lingering in his glass for the past fifteen minutes and asked for the check.

When Henrique or Miguel or whomever dropped off our check, he pulled out his wallet and said those lovely three words every guy likes to hear on a first date: “Wanna split it?”

Once we were out of the restaurant, I cheered to myself that I was free and I could run home, put on Pretty Little Liars and play Candy Crush. That was, until he offered to walk me home.

“No, no. That’s really okay!” I practically yelled. “It’s out of your way. The bus stop is right here!” But he would not let it go. So, okay fine. I let him walk me home because, in all my life of dating, no one has ever walked me home to my front door, so I was actually pretty excited about his chivalrous gesture.

When we finally arrived to my apartment, he kissed me good night. I opened the front door to my building and looked back at him, just standing there.

“Can I walk you up?” he asked. And we all know what that means, right ladies?

Since I had three glasses of red wine and a shot of tequila, I figured why the hell not. It’s been forever since I’ve had any type of physical contact that didn’t involve a body pillow or an electric toothbrush. We went up to my apartment, and started making out on the couch. Half way through, he stopped, hugged me, looked in my eyes and said, “Damn you’re beautiful.”

So, naturally I took off his pants and gave him a hand job.

Finally by 11:30, the date was over and I could take a cold shower and head to sleep. I figured he would get the hint that I wasn’t really interested and that the complimentary handy-j was just a token for him walking me home.

But he’s texted me 6 times already this morning. Time to move or change my phone number again.

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