One Tuesday night after work I made my way to a coffee shop to meet Jennifer.
When summertime finally decided to make its long-awaited appearance after a frigid spring my bevy of girlfriends and I decided to buy tickets to a singles yacht cruise, assuming meeting guys face to face would be a much more civilized approach rather than swiping on our smartphones as we had been.
We put on our nicest cocktail attire, and looked forward to a night of hor-d’oeuvres, an open bar and hopefully some eligible bachelors on our nautical excursion.
We took a seat at a table before getting underway, and had a few snacks to prepare ourselves for for the many drinks that would inevitably be consumed in the evening ahead.
The ship set sail, and we couldn’t help but be disappointed with the sea of estrogen that filled the boat.
The girl to guy ratio was approximately 10:1.
Determined to have a good time despite the
taco fest unfortunate situation, we kept the drinks flowing and enjoyed the views of our beautiful city.
Tyler was a pretentiously dressed pretty boy equipped with a gold chain around his neck and a shiny Hermes belt buckle fastened around his hips securing the designer denim he was wearing.
“Hey. You guys are here for the singles thing I assume?” He asked.
Considering the ‘singles thing’ was the only thing taking place on the boat that evening we gave him an obvious nod.
“That’s cool. I’m just checking things out. I actually own the boat. I’m up from my place in Miami just making sure everything is going smoothly.”
“Oh. OK. So…is it going smoothly?” We asked, slightly intrigued with his blatant haughtiness…in a train wreck sort of way.
“Yeah. We got a few hotels up here and down in Miami. My name is actually Tyler Hanlon**, so you probably know my family.”
My friends and I simultaneously looked around the table at each other trying to see if the name rang a bell for anyone.
“I’m not just a rich kid though, I’m really involved and have a lot of responsibility in all the family businesses,” he assured us.
After spouting off some more casual details about his privileged existence Tyler decided to go in for the kill.
“So, if you guys are going to be out after this I would be down to chill. Can I get one of your numbers?”
Again, all of us looked around waiting to see if anyone would fall on the metaphorical grenade and relinquish their digits.
Not one of us volunteered, and it was clear Tyler would be spending his evening by his lonesome.
“Whatever. You guys aren’t even that cute. I usually party with models and not ugly girls like you.”
Thanks, Tyler. You’re a real gem.
**name has been changed to protect privacy of douche bag.
Just before the six (unsuccessful) months of my eHarmony membership was up, I matched with Craig, a baby blue-eyed recently divorced social media strategist. Craig and I decided to meet for a drink after the work day one Thursday night.
Normally I would consider someone who was fresh off the ending of a marriage to be a slight red flag, but as I was rapidly approaching my 32nd birthday I decided it would behoove me to
lower my standards cast a wider net and expand my horizons.
When I got to the wine bar of Craig’s choice he greeted me, and handed me a glass of Malbec. I our previous conversations via eHarmony I had mentioned that it was my drink of choice, but was found it quite strange that someone I had never met would order me a beverage without me present.
Nonetheless, I thanked him for being thoughtful, and prayed it wasn’t roofied.
After twenty minutes of illustrating his tedious day-to-day routine of crunching cloud-based algorithms…..or whatever the fuck he does, I briefly summarized the the
riveting work I do as an corporate accountant.
Our conversation thereafter was reasonably entertaining, and I was feeling rather hospitable that evening in particular, so I suggested Craig and I continue our little rendezvous back at my place.
We were on my couch enjoying a civilized glass of wine and rather civilized conversation when my roommates returned from a bar hopping extravaganza only to continue the party at our apartment.
Craig and I gladly joined in the fun of polishing off an entire bottle of tequila.
Clearly in no shape for sexual activity or a journey back to his own place, I invited Craig to pass out in my bed.
I woke up early in the morning to him standing in front of my closet.
Then I heard it…
Craig was pissing all over the floor of my closet.
All over my shoes.
All over my hamper full of clothing.
After coming to grips with reality and noticing that it was in fact my wardrobe and not a toilet in which he was pissing in, he apologized, and made an attempt to salvage my belongings from his mid slumber urination.
I had Craig carry the contents of my hamper to the basement to the washing machine, then threw him out, along with several pairs of perfectly good suede boots.
After taking a much needed spiritual hiatus from the chaos that is the online dating scene I decided I’d better throw my hat back in the ring and attempt to meet someone before the impending wedding season began. I was hopeful that this was finally the year I would take advantage of my ‘plus one’ option.
Soon after I matched with Patrick on Tinder.
Patrick was a svelte gentleman with dirty-blond hair and slightly on the metro sexual side. His jeans were somewhat tighter than my liking but I figured I could overlook something as minuscule as the size of one’s pants so long as I am pleased with what is underneath.
Patrick invited me out on an unseasonably warm Saturday afternoon in February on a patio for some margaritas and some guac whilst soaking up the inevitably short-lived sunshine.
The date went surprisingly well, and I decided it wouldn’t hurt to bring him back to my apartment I recently moved into to show him my new digs and perhaps another cocktail.
We were sitting on the balcony engaged in a random conversation about astrology when my roommate came out to say hello.
She switch on the lights.
“Oh fuck,” Patrick said.
I glanced at Patrick as he stared at my roommate with a horrified look on his face.
“Well hello,” my roommate said as if she had caught someone with their hand in the cookie jar.
Confused, I awaited an explanation.
“So remember the guy that I was having sex with who told me he couldn’t see me for a long time because had mono and was contagious? YUP. That’s him.”
We busted Patrick’s balls for being a cowardice little shit and he split.
Big city, small world.
I met Brandon on Plenty of Fish because let’s be honest, I moved to New York City a few months prior, and any money I make seems to evaporate into thin air. Shelling out $40/month on a Match subscription was certainly not in the cards considering the lack of funds in my bank account.
Brandon was hot. He had blond hair and blue eyes which looked especially adorable when framed by the worn out brim of his Syracuse baseball cap. Despite him being a few years my junior he seemed to relatively have his shit together.
We met at a German beer garden in Chelsea, and enjoyed some local brews while nibbling on a giant fresh baked pretzel with stone ground mustard for dipping.
Brandon and I were so enthralled in intellectually stimulating conversation that we lost count of how many beers we had consumed.
Feeling rather toasted, I said that I was going to return to my apartment…
And that he should come too.
After some aggressive necking in the back of the taxi and up the elevator we landed on my bed to continue our adult recreational activities.
Brandon pulled away and paused for a moment…
rolled over to the side of the bed…
and blew chunks all over the floor.
For several minutes Brandon violently heaved while emptying the contents of his stomach all over my Pottery Barn area rug.
Too drunk to do anything about it, we both passed out.
I woke up the next morning to the putrid smell of vomit permeating my tiny studio apartment, so I gave Brandon a nudge to wake up and somehow take care of the situation.
He stumbled to his feet still seemingly inebriated while trying to assess the situation.
He then slid the area rug out from under the bed, rolled it up tightly and threw it over his shoulder.
I never heard from Brandon again, but I did discover a mysterious Pottery barn gift card in my mailbox one week later.
As a fledgling New Yorker I decided there was no time like the present to dip my toes into the dating pool by downloading a few apps and seeing what kind of possibilities laid before me.
Christina was one of the first girls to message me on Bumble. This 25 year-old segment producer was certainly physically pleasing and being that she was a college basketball fan much like myself, I thought I would take a stab at it and invite her out for a cocktail or two.
I selected a charming wine bar located in close proximity to Christina’s apartment in SoHo, and arrived promptly at seven PM.
It was obvious to me that Christina relied on the help of some filters or other photo enhancing applications to improve her appearance on my iPhone, but she still seemed quite appealing nonetheless.
We spoke about where we were from and what we did for a living, but considering March Madness would soon be upon us, we dove right into our beloved college basketball.
Being a graduate of University of Maryland Christina was quite passionate about her Terrapins.
While exchanging opinions about the first round of each other’s brackets I noticed a dewy mist glazing over her green eyes.
“Are you OK?” I asked, worrying if something I said had upset her.
“I’m sorry. It’s just so hard to talk about college. It was the greatest time of my life, and I just miss it, and I feel like I will never be as happy again. I just want to go back to football games and life when I had no responsibilities. I have been so depressed every since graduation, and I hate it,” she forlornly revealed.
Bewildered at what to say to this emotional stranger with severe Peter Pan syndrome I awkwardly placed my hand on her shoulder and murmured some senseless condolences.
Christina and I sat there for another two hours whilst she sucked down several glasses of wine despite the slurring of her speech.
I decided it was time to get her home, so I escorted her to her apartment and attempted to say my goodbyes.
“Come up with me for one more drink,” she pleaded.
Though I knew it was a horrible idea, I felt the waterworks might begin again should I decline her invitation.
We entered her apartment and the second I sat on the couch Christina straddled me and wrapped her lips around what felt like my entire face.
Completely turned off by everything about this woman I gave her a gentle nudge, and told her it was best she get herself to bed.
“WHY DON’T YOU WANT ME? WHY DOESN’T ANYONE WANT ME? I MAY AS WELL THROWN MYSELF OUT OF MY WINDOW!” she said, in between dramatic sobs of despair.
Worried that she may in fact throw herself out of the window I tried my best to calm her down, and hoped she would soon pass out.
I spent the next hour comforting this tearful stranger and explaining that life after college actually isn’t so bad.
“Will you please just come sleep in my bed and hold me? That’s all I want. I promise I won’t try to have sex with you.”
Right at this moment, her roommate emerged from her bedroom, clearly agitated by all the racket. “You can just go. She does this all the time. She won’t jump out the window, I promise,” she said confidently.
Ecstatic to be relieved of my suicide watch duties I gingerly pushed Christina’s head from my shoulder and bolted for the door…
…then quickly removed my toes out of the dating pool for a while.
Mason and I were introduced through one of my colleagues when he crashed our company’s happy hour. After conquering our Q3 goal we were a rowdy bunch certainly ready to tie one on for the evening.
With platinum blonde tresses and juniper hued eyes, this New Hampshire-born web designer had me smitten from the get go.
After chatting for several hours it was to my dismay that Mason left the event sans my contact info.
I continued celebrating into a blacked out oblivion the rest of the night, and by morning Mason was merely a figment of my imagination.
Until he messaged me on Instagram.
After exchanging several coquettish messages via DM, he invited me to a light show at the New York Botanical Garden, and I was back to being rather smitten with Mason once again.
We perused the illuminated exhibits of ethereal splendor that were displayed for the public and commented on the work of each artist. We enjoyed some vodka cranberries along the way along with some light bites in between our rather pleasant conversation.
As the show concluded we cabbed it back to the Upper West Side to continue our
alcohol consumption conversation.
Mason and I finished off a bottle of Shiraz, and though I very much enjoyed his company and wanted to see him again, I decided going home to my apartment alone would be the courtly thing to do.
He gently took hold of my chin and pulled it toward his face for a kiss.
Minutes later we remained on the corner of 79th and Amsterdam somewhat passionately engaged in a full-on make out session.
Mason reached up my blouse to touch my stomach. Having a pretty good prediction as to where he was going with this I removed his hand from the direction which it was headed.
“Not so fast,” I giggled coyly.
“You don’t have to feel uncomfortable,” he said.
“I’m not. I just don’t want to be felt up on a street corner. That, and I’m not into moving that quickly,” I assured him.
“Oh, I thought you were uncomfortable because you have a little bit of a tummy, which I actually like.”
“…” (floored expression)
“Seriously though, I am not interested in your body. All I am really interested in is your soul. I just want to know your soul.”
At this point I was having severe difficulty trying to figure out whether I was more offended by him commenting on my supple midsection or creeped out about him seemingly wanting to consume my soul, but I decided it was time to hightail it home.
After an agonizingly long day at the office I made my way to the A train and back to my apartment in West Harlem intending to catch up on Game of Thrones and pass out next to a carton of half-eaten Kung Pao chicken. A glamorous life I live, indeed.
I was fortunate enough to score a seat at the height of rush hour where I settled and got ready to relinquish all attention to my beloved kindle for the duration of the commute.
“Confessions of an Economic Hitman,” a stranger next to me said. “Great read.”
Being that I had just started the book on my way to work that very morning I had no viable opinion to offer, but I soon found myself discussing other pieces of literature with Liam, a devilishly handsome certified public accountant residing on the Upper West Side of Manhattan.
Before he exited the train we had exchanged numbers, and planned to grab drinks that very week.
Like many boys in New York City, he was not one for forming a definitive plan, but rather texting sporadically at various hours of random evenings asking if I would like to
hook up grab a ‘last minute nightcap,’ which I always respectfully declined.
One Friday night subsequent to an evening out with my girlfriends that involved an over abundance of gin and tonics, Liam proposed we grab one more drink at a bar in close proximity to my apartment.
“A great idea!” I said.
This is was not a great idea.
I don’t quite recall the details of our spontaneous rendezvous, but long story short, we woke up in my apartment side by side, scantily clad with remnants of mozzarella sticks strewn throughout the sheets and a half-empty bottle of wine on my night stand.
I got up to go to the bathroom to quench the insatiable thirst and rid myself of the remaining gin, wine and marinara sauce that lingered inside my mouth.
When I crawled back into bed Liam was awake, and informed me that he was going to jump in the shower. I drifted back into my slumber fully expecting (and hoping) that there would be no trace of him when I awoke.
I was finally awaken by the sound of a frying pan screeching against a rusty burner and the sizzle of freshly cracked eggs accompanied by the delectable smell of sautéd butter.
I ascended the stairs of my duplex apartment to find Liam, stark naked, cooking up breakfast.
To my horror, his dangling testicles were quite literally pressed up against the knobs of my oven.
“Breakfast?” He asked, cheerfully, which I found even more obnoxious than his balls on my stove.
“No thanks,” I said, finding it hard to fashion any sort of appetite. “I am going to take a shower and get started with my errands and such.”
My ‘errands’ consisted of ordering the greasiest sandwich in existence and nursing my hangover on the couch, but I would have said anything necessary to expedite his departure.
When I finished my shower I was astonished to find Liam in my living room, his feet comfortably propped up on my coffee table, scrotum displayed for my viewing pleasure, and casually enjoying
his my eggs. For a minute, I thought he owned the place.
“Do you not have Netflix?” He asked.
Growing increasingly perturbed with his offensively entitled behavior…and his balls all over my stuff…I told Liam it was time to make his exit.
We ran into each other on the subway several times after our little ‘encounter,’ but Liam and I never spoke again.
After the difficulties that ensued from my terribly unsuccessful engagement I regrettably found myself back in the harrowing arena that is online dating.
“Join Match,” they said. “You will meet a nice guy,” they said.
Desperately trying to move on from my failed relationship of five years I audaciously swiped through my matches with hopes of starting anew.
Logan was a fair-skinned and particularly aristocratic-looking specimen. Armed with a charming pick up line and a recently completed masters degree in computer science, he had me quite intrigued to accommodate his request for an in-person meeting.
Being relatively new to the millennial phenomena that is online dating, I figured Logan would suggest we meet at a bar or coffee shop of some sort, so I was delighted when he suggested we go to a wine and cheese tasting event he had purchased tickets for.
Wine and cheese are certainly the direct route to this gal’s heart.
Logan and I settled into a quaintly romantic brasserie and exchanged light badinage while waiting for the instructor to begin the tasting.
Soon I found myself very much enjoying our time sampling various French burgundies, discussing the flavorful aromas of each and deliberating which cheeses complemented them the best.
As the instructor concluded her presentation we continued getting to know each other over the remainder of our vintages.
To my dismay, I had to bring the date to a close as midnight rapidly approached, and my speech began to noticeably slur.
I told Logan what an enjoyable time I had and expressed my desire to to see him again, hoping the feeling was mutual.
“Do you have to go home now? It’s so early!” He pleaded.
“I have to be at work at seven tomorrow, so I think it’s for the best. Plus, I have already had a lot to drink,” I said, slightly abashed by my tipsiness.
“We don’t have to drink anymore. I’m sorry, I’ll just say it. I would love to take you home and eat you out. You won’t even have to do anything to me,” he said, expecting me to be eternally grateful for his offered services.
Dumbfounded, all I could do was cackle in embarrassment on his behalf.
“Or, we could just cuddle. I’m a great cuddler too,” he threw out as a last ditch effort to get me into his apartment.
I’m good, Logan. I’m good.
I arrived at a wine bar quietly tucked away in the West Village to meet a northern California transplant named Karl for the first time.
According to his profile pictures on Hinge, Karl seemed to flawlessly fit the bill for me as far as physical attraction is concerned.
He was preppy, but not obnoxiously so, stood just over 6’2 and was clearly well-educated as he had recently finished his MBA at Stanford.
I too was a recent MBA graduate who had completed a stint living in San Francisco, so I surmised that we would inevitably have much in common to fill a conversation over a bottle pinot.
Karl was seated and waiting for me when I arrived. He stood up to offer an embrace…and then I saw it…
The horror of golden brown tresses wound tightly together sitting atop the crown of his head.
A man bun.
This was definitely not depicted in his photos.
Attempting to keep an open mind, I thought if we did get along that one day I could possibly
shame him into cutting it off convince him into trying a more suitable hair style.
Karl was a self-proclaimed wino with an affinity for red vintages. Being more of a whiskey gal myself, I told him to feel free to make a selection based on his preferences as my palate was clearly not as sophisticated.
He found a bottle he seemed particularly enthusiastic about and assured me I was in for a real treat.
Our waitress performed an impressively sensational wine service as she carefully decanted the bottle and poured it into two long-stemmed globes of crystal for us to taste.
Karl was extremely pleased, while I secretly thought it tasted no better than the $17 boxed wine I had while partying at the Jersey shore the previous weekend.
The conversation between Karl and I was disappointingly stale. Being the generally amiable person that I am I found it oddly difficult to connect with him on any subject matter whatsoever.
As the date came to an end I thought it was clear it would be the last time Karl and I would make each other’s acquaintance.
The check arrived and I offered to pay half my share. Karl, assumably agreeing that the evening was a bust, gladly accepted my attempt.
When the bill came back I reached for a pen to sign my receipt and be on my merry way when I was hit with the sudden feeling of shock and horror.
My total came to $212.50.
Two-hundred twelve dollars. And fifty cents.
“There must be some mistake,” I said, siphoning through the multiple papers in the black book before me searching for an explanation for this astronomical amount.
“Ah, the bottle of Bordeaux we got was actually a pretty special year for that vineyard and a particularly rare bottle, so I couldn’t pass it up. I guess it was a bit pricey,” he admitted.
With a blatantly obvious eye roll I resentfully put my John Hancock on the piece of paper.
Before we made it out of the bar I had a Lyft on its way to my rescue, but Karl had other plans.
“So, did you want to come back to my place for a night cap or two?” He asked.
Never was I so happy for the arrival of a Lyft.