Group-On Turn-Off

I met Jimmy on OK Cupid when the sweet summer had come to an end and it was time to trade in rooftop afternoons filled with sparkling Rose for football games and pumpkin spiced…anything.

It was also time for me to get my head back in the dating game as my 33rd birthday was rapidly approaching and the number of single friends I had seemed to be dwindling by the hour.

For some reason, OKC seemed like the perfect place to start getting my shit together.

Jimmy suggested we meet at an elegant fondue restaurant with baroque-style decor in Williamsburg on a Tuesday evening after work.

He had adorably boyish features and was an unpretentiously dressed New Jersey native who worked as an accountant for the Chrysler Corporation.

Perhaps he wasn’t exactly my type considering the slightly metro-sexual men I have inexplicably been attracted to in the past, but I still found myself excited to delve into conversation and enjoy his company.

The evening was quite romantic as we huddled over our steaming pot of molten swiss cheese accompanied by sliced baguette and an assortment of crudite vegetables.

We discussed our mutual desire to one day complete a week-long camping trip though the Grand Canyon and taste wine in Napa Valley as well as eventually become dog owners while remaining in the great city we both currently called home.

After we polished off the last of the cheese we satisfied our sweet tooth with  some decadent dark chocolate fondue laced with caramel and marshmallows.

Minutes later the bill arrived and Jimmy assumed responsibility for it despite my best effort to contribute.

“I am so sorry,” she said sympathetically. “I cannot accept this Groupon voucher as it expired a month ago.”

“I still paid for it, though. You can’t just make an exception and take  it?” Jimmy pleaded.

The waitress denied his request yet again, and Jimmy summoned a manager.

Slightly abashed by the scene being caused in such a small venue, I told Jimmy he should cut his loss and split the bill with me in order to expedite our escape from the embarrassing situation.

Jimmy refused and argued relentlessly with the manager to honor his expired voucher he purchased for $50 in order to receive a $125 credit towards fondue meal in return.

When the manager finally made it clear that he (rightfully so) would not accept it as payment, alas Jimmy relented.

“So, yeah, can we just split this then? I would pick it up, but I already wasted $50 on this Groupon which they are clearly not going to take,” he said.

I handed him my credit card.

“Oh, you don’t have cash? All I have is cash.”

“No sorry, I never carry cash. You don’t have a card on you?” I asked, assuming we would split it down the middle as discussed.

Jimmy put down $85 in cash, which was apparently all he had in his possession at the time.

“Sorry, I didn’t realize I wasn’t going to get credit for the Groupon, and I don’t have a card on me so this is all I brought. You mind just grabbing the rest and I will get you next time?”

The bill came to $175 not including tip.

Spoiler alert: There wasn’t a next time.


I met Stacey at a conference for the industry we are both gainfully employed in.

Manning the booth for my tech start up I saw Stacey coming from across the room with with a magenta pencil skirt, three-quarter length blazer and some black pumps that were clearly doing her already lengthy, toned legs some serious favors.

Her blonde hair was in loose waves falling just passed her shoulders she extended a hand to meet mine. With her big white smile on display she dauntlessly introduced herself.

Slightly enamored by the attractive specimen that stood before me I can’t quite recall what Stacey had to say about the the services her company provided, but it did turn out that we coincidentally reside in the Bushwick area of Brooklyn.

We exchanged business cards, and shortly after I asked if she would be interested in joining me for a non-work related dinner…A date.

To my relief, she was game.

I made reservations at a posh Asian-fusion restaurant in Manhattan that has never failed to impress.

Stacey showed up and was looking quite ravishing in her crop top and high-waisted skinny jeans.

I pulled out her chair and we both began studying the menu.

“Is there anything you don’t like to eat sushi wise?” I asked.

I looked up to await her response to find her pouty lips pressed together, her head tilted back with her arm extended, cell phone in hand.

She was taking a duck face selfie.

Stacey spent the next 45 seconds snapping pictures of herself at different angles, carefully analyzing them, then repeating the process.

When she finally had mastered the perfect selfie, she set her phone aside to discuss what we would be dining on.

During our discussion about the menu she repetitively glanced at her cell phone placed on the table in close proximity to her right hand.

The first round of small plates came, and right as my chopsticks were about to grab a piece of rock shrimp tempura Stacey ordered me to a halt.

“I need to take a picture first! It all just looks so pretty!”

After snapping five or six pictures I figured it was safe to enjoy my meal.

“Wait! Now I need to make a snap for SnapChat!”

Again, after a minute or two I was finally permitted to eat.

We ordered a few martinis from the specialty cocktail list and of course, Stacey had to capture a selfie, complete with her frosty pink glassware daintily garnished with a slice of watermelon and basil. She then selected her filter and hashtag of choice so it was finally ready to be posted on her beloved Instagram page.

After checking her phone for the tenth time to obsess over the number of likes received, I was struggling to bite my tongue.

“So, do you have to check your Instagram every minute or are you waiting for an important call? I am just noticing that you keep looking at your phone so I didn’t know if you had somewhere else to be,” I said.

“Sorry, I just love Insta! I will try to ignore it until we are done with dinner.”

“Is it really that hard? Why don’t you just take it off the table and put it in your purse? That would probably be less tempting,” I suggested.

“Ahh I just like it right here. I don’t like to be too far from my phone because then I just feel so disconnected. Also, it’s not like I am just obsessed with Instagram, it’s more about building a brand and getting a following.”

“What brand is that? Are you starting a company?” I inquired.

“No it’s just about personal brand. Everyone should just think of themselves as a brand and I feel like social media is the way to get yourself out there.”

Without consulting Stacey I told the waiter we would skip dessert. I paid the check and cut my losses.



A Serious ASS-umption

Ethan and I met through a mutual friend we both went to college with.  I was privy to the idea of meeting someone the good old fashioned was as opposed to the plethora of dating applications I had been miserably failing at, so when he invited me for drinks I delightfully accepted.

After some scheduling mishaps, Ethan texted me and suggested we grab some refreshments at a rooftop hotel bar on a warm summer night.

A fabulous idea, indeed!

Being that it had finally hit the 80 degree mark in New York City I selected my girliest flouncy sun dress with a pair of statement earrings and some strappy nude heels. The wardrobe and I were both ready for summer to be in full swing.

My first thoughts after seeing Ethan in person was that he looked just as adorably handsome as he did in his Instagram photos.

Ethan was a tall and lean California boy with a slightly tattered head of hair and just the right amount of 5 o’clock shadow skimming across his perfectly structured jawline.

I hoped very much that he would find me equally as attractive.

We took a seat in the back corner of the rooftop and patiently awaited a server to take our drink order.

We made a few comments about how glad we were to finally see the sun subsequent to a notably frigid spring, then got to talking about the basics of where we were from, and what we do to support ourselves in the monetary vacuum that is New York.

The server brought over our requested Montauk Summer Ales and as he gingerly poured it into his frosted pint glass decided to give me a little heads up about something on his mind.

“So just letting you know, I want to be friends first. I am not going to jump into sleeping with you right away or anything serious. Wanted to put it out there before we go any further. That cool with you?” He asked.

“What would make you assume I would want to sleep with you or be anything more than friends ever? I just met you five minutes ago. You really shouldn’t flatter yourself so much,” I clapped back cheekily.

“I don’t know, you are all dressed for a date. Some people want to jump straight into something whether it be sexually or a relationship and I am just saying I require us to be friends first.”

“I like this dress, so I wore it. I would have worn the same thing if I came out with my girlfriends tonight. But anyways, you to not have to worry about me wanting to be anything more, I can assure you of that,” I graciously informed him.

I finished the remnants of my beer and pulled a Hamilton out of my clutch to cover my share of the drinks.

“Oh no, I got this,” he offered.

“Thanks, but apparently this wasn’t a date.”


The Blunder From Down Under

Neil and I connected on After reading 300 or so agonizing messages I received while away on vacation his was the only one somewhat worthy of a response.

Neil was fresh off the boat from Australia and touched down in the big city to head up the investor services branch of the Australian bank of which he was employed.

He suggested we meet at a trendy spot that recently opened in the West Village to check out the craft cocktails and farm-to-table bar bites while getting to know each other away from the computer screen.

Our meeting time was for 8 o’clock, and as I was rendering the doorman my identification at precisely 8:02, I received a a text from Neil informing me that he got caught up on a phone call at work and would be yet another 15 minutes.

Slightly perturbed with the timing of his message as I myself had rushed from the office to ensure my punctuality, I shook it off and took a seat at the bar to await his arrival.

Neil graced me with his presence 20 minutes after our agreed meeting time and offered up a half-assed apology for his tardiness.

Perhaps I would have been more miffed at the inconvenience but his Aussie accent was simply too charming to remain in such an aggravated state.

That paired with his precisely pressed Brooks Brothers suit and flawless complexion, I was desperately hoping this blunder wasn’t an ominous warning as to how the remainder of the evening would play out.

We ordered a couple of whiskey cocktails, some lamb sliders, a chickpea salad and some fried goat cheese.

Neil was halfway through the story about what prompted his decision to move across planet Earth when he glanced at his phone to check the time.

“Oh! I forgot to mention, I have to join in on a conference call at 9. It shouldn’t take too long though,” he assured.

“No problem,” I said, confused as to why he would plan a date on a night when he had business to conduct.

He excused himself to take the call leaving me in solitary with my whiskey sour.

Five minutes went by.

Then fifteen.

I would have left had it not been for my insatiable appetite and the thought of the sumptuous lamb sliders that were sure to arrive any minute.

The food finally arrived and I stared at it longingly while anxiously anticipating Neil’s return.

After another five minutes had passed I decided I had waited long enough. It was time to indulge.

Approximately 35 minutes later Neil reappeared and aloofly offered his condolences.

I had eaten all but one lamb slider, and wished him well.

Chivalry Isn’t D….Oh Wait, Yes It Is.

I was excited to finally be off the waiting list and an official member of a dating app entitled ‘The League’ where its participants are pre-qualified to ensure that everyone is educated and gainfully employed. Being that I possess both of these attributes, I was looking forward to finding the same.

I matched with Andrew. Andrew was a 38 year-old Princeton graduate who worked as a quantitative trader for a hedge fund here in the city. His hair was quite disheveled and his pants just barely grazed the tops of his ankles, but there was something about his nerdy characteristics that I found particularly endearing.

We settled into a table on the rooftop of the Hudson Hotel overlooking the beautiful views of Manhattan and sipped on some red Sangria.

The weather, the view and the drinks were undoubtedly  gratifying, but the conversation was terribly monotonous. We proceeded through the motions of chatting about where we grew up, went to school and…I dunno. Whatever else.

After my second glass of Sangria I casually mentioned how late it was getting and that I had a meeting early the following morning in order to wrap things up.

We exited the hotel, and to my surprise Andrew attempted to demonstrate an act of chivalry that I had considered long vanished.

“If you don’t mind, I would love to be a gentleman and treat you to your cab home,” he said sanguinely.

Flattered and not wanting to insult the man, I graciously accepted his generous offer.

At this point I was expecting him to nobly step to the curb, hail me a yellow taxi and open the door, or to summon an Uber from his cell phone, but neither of these scenarios came to fruition.

Andrew pulled his wallet from his back pocket and slapped a bill in my hand.

I was even more astonished by this act when I looked down to see a $100 note.

“Sorry, I don’t have anything smaller,” he said begrudgingly.

“Oh, no please, I’m not taking this. The train is right here and will actually be much faster,” I said, somehow feeling like a prostitute when I didn’t even have sex.

After exchanging insists about who was to leave with the Benjamin he finally placed it back inside his bill fold.

Considering he was so adamant about displaying his courteous manners, I completely expected him to escort me to the entrance of the subway.

Nope. That didn’t happen.

Andrew jumped in his own car and was gone with the wind.

The D*ick I Don’t Deserve

Shortly after my breakup with my boyfriend of two years I decided to put down the Ben and Jerry’s and seek the companionship of a new suitor.

For some odd reason I decided Tinder was the best method of seeking said companionship. Why? The world may never know.

Enter Tyler. Tyler was a highly educated venture capitalist who claimed to be one of the early investors in SnapChat. Though he had a slightly haughty air about him, I found a peculiar attraction to his unquestionable confidence.

We took our seats at the bar of a slightly pretentious eatery in the Meatpacking District of Manhattan and proceeded to order a couple of specialty martinis off the cocktail list accompanied by a dozen Wellfleet oysters and some Pellegrino with lime to wash them down.

Tyler wasted no time in informing me about his life and his notable achievements. He explained how he graduated from a top-tier university and landed his dream job at a venture capital firm, and how he had successfully accomplished his goal of purchasing a condo on the Upper East Side by the tender age of 33.

Despite him coming off as undoubtedly pompous, I couldn’t help but be slightly enamored by his sophistication as well as his tenacity.

After a few drinks at the first establishment we decided to move onto the next. And then another.

Around 1 o’clock  AM we were both feeling marginally tipsy, and my new Vince Camuto stilettos I was donning were becoming increasingly difficult to promenade around the city in.

“How about a drink at my place,” he suggested, putting his perfectly aligned grin on display.

“Well, I guess one nightcap won’t hurt,” I said, hoping he would take the hint that this would not result in my clothes on his bedroom floor at any point in the evening. “Let’s get a cab then?”

“Nah, we can just take the train,” he said.

For those of you who do not reside in New York City, taking the subway from the Meatpacking District to the Upper East side is A) quite the hike, and B) not a particularly safe hike at such a late hour.

“Hmmm. By the time we got there it would be almost 2:30 in the morning, and I would just have to go home. Also, these heels are killing me,” I said, attempting to consider the logistics as well as garner sympathy for my current physical condition.

“If you want to take a cab to my place we can, but you’re paying for it. I will pay for it if you’re staying but not if you’re just going to turn around and leave.”

And with that, I summoned an Uber and disappeared into the night, sans Tyler.

Unfortunately it wasn’t the last time I heard from this strapping young gentleman…

aBANDon Ship

Dennis came into my life as a result of drunk Tinder swiping after a happy hour that went on for far longer than it should have.

Dennis was a slightly reserved yet intriguingly confident Google engineer with a pair of lustrously shiny black boots that were obviously more expensive than mine.

The red tape was severed rather quickly, and soon after chatting via text I found myself making my way to an upscale Irish pub to meet Dennis in the flesh.

Subsequent to our remarks of disbelief about the unseasonably cold spring we had been experiencing, we engaged in the ubiquitous conversation of what we do for a living.

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 internet marketer.

“I can tell you all about it when you have trouble sleeping one night,” I said facetiously,  not being one to talk too much about myself.

I then found myself being interrogated by Dennis as to why on Earth I would continue working in an industry that I lacked true passion for.

“I like my job a lot. I get to talk to people, I have a lot of freedom and it provides me a nice living in New York City, so I can’t complain one bit,” I explained.

“Yes but if you don’t absolutely LOVE something, why would you do it?” He asked, bewildered by the fact that someone would be so responsible to work in a respectably stable state of employment instead of running off to join the circus.

“I am also a professional singer, and I’m extremely passionate about that. I am in a wedding reception band as well as a 90s cover band. I get to do that most of my weekends. I feel very proud when a bride and a groom approaches me to tell me that my band made the most important night of their lives a great success. I also love 90s music and I love to see people singing along and having fun with me during our concerts.”

Dennis stared at me as if I were on methamphetamines.

“How old are you again? Thirty, right? So at what point are you too old to do silly stuff like this?” He asked dubiously.

“Oh, I don’t know. How about when I’m dead?” I replied.

“Full disclosure, I am looking for someone who is a bit more serious about starting a life and a family. Are you going to be caught up in this band stuff for a while then?”

Yes, Dennis. Yes.


See Ya Later, Litigator

I have OK Cupid to thank for gracing my presence with the specimen that is Jesse.

Jesse was exceptionally intellectual, equipped with a PhD in philosophy, and was an accomplished corporate litigator. Being slightly intimidated by his achievements I was quite relieved when he suggested we meet at a divey hole-in-the-wall in Brooklyn where we both just so happened to reside.

Scholarly, gainfully employed AND not too pretentious? We are off to a promising start.

I ordered my typical Jack and Coke while Jesse opted for a Patron Silver with lime.

We sipped on our beverages while discussing the peculiar personalities we both encounter at our places of employment and our rapidly approaching milestone birthdays, mine being my 30th and his the dreaded 40th.

As the remainder of ours drinks went down the hatch I was fully expecting Jesse to suggest we order another round as the conversation seemed to be flowing quite effortlessly.

He slammed his glass onto the timber countertop with an obvious sense of finality.

“So, where are we doing this? My place or yours?” He asked rather aggressively.

“Come again?” I said, thinking that I must have misunderstood the words that were being spewed from his supposedly intelligent mouth.

“Sorry, I haven’t been single for very long and I’m not sure how these apps work and what not.”

“I mean…they work just like this. We get drinks, we decide if we want to see each other again and we see where it goes. There really isn’t a checklist of things to do,” I said, doing my best to educate him on the pervasive phenomenon that is dating from the Internet.

“Ah OK. Perhaps I should have been more clear. I just got out of a long relationship and I am actually just looking to have some fun, so if you want to grab a bottle of red and go back to my place we can do that, but if you’re actually looking for a relationship I don’t think I’m your guy.”

HAH. Peace.

Check Yourself, Not My Watch

I met Andrew on Bumble, and after chatting for a brief period of time I opted to meet him for drinks at a craft cocktail lounge in Soho after work one evening.

Andrew claimed to be a ‘real estate investor’ when in reality, he was a real estate broker. Now, there is absolutely nothing negative whatsoever about one who works in such a profession, but it did give me a sense of dishonesty on his part.

We sipped on our cocktails while I mostly listened to him talk about his sister’s dog and…I don’t even remember, but not one question was asked about me and my life.

I attempted to give him the benefit of the doubt and stick with him for at least another round. After all, I didn’t wash my hair that day to only have one drink.

As the liquor started to sink in and my body temperature increased I decided to remove my sweater. It was at this time that my watch that I am fortunate enough to call my own was exposed to Andrew, and he eerily would not take his eyes off of it.

We engaged in a conversation about how both of our grandfathers were vastly approaching their birthdays in which they would officially be one century old. We exchanged knee-slapping stories about how economically  frugal one can be when being raised in the Great Depression era.

“So you are telling me your grandpa would never be one to buy a Rolex?” He asked presumptuously.

“No. Absolutely not. He won’t even buy a coffee at the 7/11.”

“You know why I said that, right?” He muttered suspiciously.


“Because you’re wearing a Rolex.”

“…..OK?” I said, confused as to where exactly he was going with this information.

At this point Andrew thankfully changed the subject to how utterly famished he was. He summoned the waiter and ordered a skirt steak with a side of Brussel sprouts and red-skinned mashed potatoes.

Though I had already eaten prior to the date I elected to order a side salad in order the avoid the awkward situation that is eating alone.

When the check arrived Andrew took a glance and placed it on the table.

“Judging by what you are wearing on your wrist, I think we can split this.”

I surrendered my Visa, but insisted he leave the tip seeing that his portion was significantly greater than mine.

We exited the establishment and I told him that I was headed south to the nearest 6 train entrance. Not that I wanted to spend another second of my time speaking to this boy, but I was raised to expect that a certain level of chivalry was meant to be common sense.

“Cool. I’m heading this way,” he said. “Get home safe!”

I assumed his lack of courtesy was due to his disinterest in me, but clearly I was wrong.


Stand Down, Soldier

After getting somewhat acquainted with Andy via, we decided it would be slightly more conducive to our busy schedules to meet for a lunch date on a Wednesday afternoon.

Andy was a recently single ex-military officer with a crisply pressed Oxford collar protruding from underneath his baby blue argyle pullover. Though he had quite handsomely chiseled features, I found myself wishing he had retired the quintessential ‘high and tight’ hairstyle when he retired from the marine corps.

Now working in finance (much like myself), we had plenty of things in common to chat about on our lunch date while dining on our lobster bisque and chicken Caesar salads.

When one thirty rolled around I decided it was about to time return to my office to prepare notes for my three o’clock meeting with an important client and my boss.

We exited the eatery, but Andy clearly had another plan in mind.

“So you have to go back already? You said your meeting was at three, no?”

“Yes, but I should get back as I have some loose ends to tie up before,” I said confused as to what else there would be to do to occupy our time in the middle of a work day.

“I live 5 blocks from here actually. We could run up to my place for a bit,” he muttered suggestively.

I couldn’t help guffaw in amusement.

“Honey, if you honestly think I am going to go back to your apartment and bang you on my lunch break, you are sadly mistaken.”

“Ehh. Figured it was worth a shot at least,” He winked at me gregariously. “Your loss.”

Sure, Andy. My loss.