The Shortstop Flop

I met Tim, a hedge fund financial analyst, on Bumble. I was pleasantly surprised at how quickly he cut through the usual monotonous red tape that is sending mundane texts back and forth via the dating app and invited me out for an evening that same week.

Upon arrival I approached Tim, who was sitting at the bar. He immediately stood up to receive me, and I was utterly astonished by the size of this boy man.

My petite frame stands just shy of 5’1, so unlike most women in the online dating community I am not often concerned with details such as the height of an individual because the last time I met someone shorter than me they were 11 years old.

To his credit, I didn’t ask, and he didn’t offer a number that was clearly fabricated at any point in our conversation or on his profile.

Donned in my ballet flat shoes, I stood about 1 and 1/2 inches taller than Tim.  Usually the one to feel particularly dainty next to 99% of guys I meet, I suddenly felt unfamiliarly monstrous towering over this miniature human.

No problem though! What does height matter if this could be someone I have amazing chemistry with, right?

The waitress showed us to our table, and right away Tim and I got to talking. After sharing the details of how our days went at the office we began discussing what TV shows we were looking forward to watching now that the weather was becoming crisper by the day.

“So are you into Mad Men?” He asked.

“That is actually one I couldn’t really get into for some reason despite the hype,” I replied.

Strike one,” he said rather aggressively.

“Strike one? So it’s a strike against someone when they don’t like the same TV show?”

The waitress came by to take our beverage order and Tim recommended I sample the Sazerac whiskey drink from the signature cocktail menu.

“I am more of a vodka or gin drinker. Not so much into whiskey.”

Strike TWO,” he said fervently.

“OK so the whole ‘strike’ thing has got to stop. It’s pretty arrogant and the fact that you put ‘strikes’ against people who don’t share your opinions on things like liquor and TV shows is pretty stupid.”

Tim offered up a pathetic apology and chalked it up to being uneasily nervous. I accepted and was prepared to start fresh.

“So you said you work in fashion merchandising? Is that even a real job or just one of those things girls get into because they like playing with clothes and stuff?” He asked.

For the sake of not having to hear him speak I sarcastically conceded and said he was absolutely correct. My bachelor’s degree in merchandizing and my master’s in supply chain management was all because I just want to ‘play with clothes’ all day.

Begrudgingly, I finished my meal despite that fact that Tim had completely spoiled my appetite and when we exited the building I had every intention of making a beeline for the 6 train to escape the atrocious company I had just endured.

“So if you want to grab another drink there is this whiskey bar I really like down the street. Although you don’t drink whiskey so I would probably be embarrassed bringing you there only to have you order a glass of wine.”

“Tim, I have zero desire to spend one more minute with you to be honest. I think you were probably the rudest person I have ever met in my 27 years on this earth. I am not saying that to be a bitch, I am being honest because I think someone needs to bring it to your attention in order for you to ever have any hope of finding a girlfriend.”

“Well I guess that is strike three then!” He said with a smile.

“Oh you struck out long ago, believe me.”

I have never been so happy to be back in my tiny studio apartment.

The next morning it appeared that Tim was not only rude, but he was also comprehensively ignorant.



I met Travis  on a balmy fall afternoon while admiring the foliage encroaching upon an Indian summer in NYC. I was strolling through Central Park on my lunch break and couldn’t help but coddle his six week-old black lab puppy.

After a bit of small talk we exchanged cards and began dating soon after. We had gone on a few low-key dates and my intuition made me feel as if Travis wasn’t necessarily looking to get serious, but being that I just turned 24 and relocated to this exhilarating city that is New York, I was perfectly content to keep my options open as well.

On our third or fourth date Travis requested that I attend a wedding with him in Long Island the following Saturday. He mentioned he had a plus one but he and his ex-girlfriend broke up six months prior and he would be delighted to have me accompany him for the festivities. Far be it from me to turn down an invitation to an open bar, I graciously accepted his invitation.

The wedding took place about an hour outside of Manhattan at a ritzy hotel and Travis told me he had secured a room so we wouldn’t have to be bothered with getting anywhere after consuming what was expected to be a bountiful amount of alcohol.

The wedding was a blast as we danced, ate and drank to our hearts content at a beautifully opulent inn in East Hampton. The fun continued at the after party when Travis began ordering drinks on the room until the wee hours of the evening while I decided I’d reached my threshold early and retreated to our room to leave him to carry on with his college buddies.

We awoke the following morning and and enjoyed a room service platter of blueberry pancakes and a western omelette with hash browns and freshly squeezed orange juice. When I saw the bill for the lovely spread that Travis took the liberty of ordering I noticed it was $96.50. This was particularly astonishing because Travis did strike me as a bit of a penny pincher.

We collected our things to hightail it to the 11 o’clock train and rushed to the front desk to check out. The total came to $787.75 including tax, Travis’ drinks the previous evening and our extravagant breakfast.

Travis turned to me apprehensively and said, “Sorry, do you mind putting this on your credit card and I can Venmo you for half later? Not really sure what the balance on my card is and I have just enough for rent and utilities on my debit right now. I didn’t realize I ordered so many drinks last night and how expensive they were.”

“Umm….I can put it on my card but why would you only Venmo me for half?” I ask perplexingly.

“Well, you stayed here as well didn’t you?” He said.

“Yes Travis I did, but you invited me as your date. Had I known a night in the Hamptons was going to cost me $400 I never would have agreed to come. Also, you were the one who decided to order breakfast while I was sleeping and I had one drink at the after party while it seems you had nine.”

“Ok, Well just pay for it and I will Venmo you for all of it minus half of the hotel. Your half would have been about $264.”

“Travis, once again, I was YOUR date. If the tables were turned I would have paid for the hotel room for YOU to come to a wedding of MY friend.”

After haggling with me for another few minutes of desperately trying to salvage some of the funds he has squandered the previous evening, I decided to grab my own Uber and head to the train.

I am not sure if he was able to cover the room on his card or if he had to wash dishes, but either way, I really don’t care.

An Emotional [Mother’s] Date

I met Justin at a singles bowling event in which my best friend basically dragged me by my hair to on a rainy evening when all I wanted was to be cuddled up on my couch binge watching Orange Is The New Black. Being the pushover that I am, off to Lucky Strike Lanes I went.

In walks Justin, a robustly bearded young gentleman with perfectly aligned pearly whites and notably masculine jawline. It wasn’t long until he was chatting me up about our affinity for traveling to exotic and unfamiliar places such as southeast Asia and our mutual obsession with Led Zeppelin.

By the end of the evening Justin and I had exchanged numbers, and I was moderately looking forward to getting drinks the following Sunday.

When the date approached I met Justin at a craft cocktail lounge on the Lower East Side and immediately I could sense that he had a rough day judging by the disparaging look spread across his otherwise handsome face.

“Are you alright?” I asked. “You seem a little bummed out.”

“Yeah. I’ll be OK,” he replied forlornly. “I just need some time.”

I assured him that if there was something he wanted to get off of his chest I would gladly be all ears but also wanted to tread lightly and avoid delving into an overly emotional topic given that it was our first date, and quite frankly, emotional situations make me uncomfortable.

After about 30 minutes of dealing with his unignorably somber demeanor I had to ask again.

“Are you sure you are OK? If you are having a bad day we can always reschedule. It is pretty clear you are un a terrible mood.”

“I apologize,” he said. “Today is always difficult for me because it is Mother’s Day and I lost my mom so it just always gets to me.”

“I am so sorry to hear that. Did she recently pass?” I asked.

“She died when I was seven, but it never gets any easier and it is especially difficult for me every Mother’s Day.”

Now, I clearly have the utmost sympathy for anyone who loses a parent at any time in their existence, but the man was 34 years old. One would think that enough time had passed where he could put his emotions aside for a first date or have the foresight to abstain from making plans on Mother’s Day if he knows it will be particularly troublesome for him to keep it together emotionally.

Justin then began to get teary eyed speaking about how growing up he and his dad were never able to see eye to eye and how he couldn’t wait to create his own family and make it absolutely perfect.

I wish Justin the best of luck but this was way too emotionally intense for a first date. 


Gift Tard

I met Erik, a 33 year-old fledgling dentist, on Plenty of Fish. Being that we were both raised below the Mason Dixon line with strong southern values I thought we could very well be an impeccable match.

Erik suggested we meet at a lovely (and pricey) steakhouse called The Capital Grille. I was rather impressed with his choice seeing that most guys I had been out with had selected some sort of shitty Irish pub that would be more suited for getting wasted with a bunch of dudes rather than a proper first date.

I arrived promptly at 7:30 PM and was pleased to see Erik already settled into a dimly-lit corner table.  He greeted me with a warm embrace and a sweet southern ‘hello’.

We feasted on a crab cake appetizer, chopped salad and petite filet mignons as we sipped on a full-bodied Chianti and discussed everything from our experiences in graduate school, upcoming international travels, and our love for our little canine children.

Overall, we seemed to get along exquisitely well, and I was positively excited to see Erik again in the very near future.

When the delicious meal came to an end the waiter brought the bill, which came to a grand total of $220. As always I reached for my wallet completely expecting this man with self-proclaimed ‘old-fashioned southern values’ would hear nothing of a woman forking out cash on a first date, but I wanted to evade seeming presumptuous.

“Oh, I have a gift card,” Erik said as he relinquished it into the billfold. “There is $250 on here, so why don’t you put half on the gift card and you can put the other half on her card.”

Shocked, I handed him my debit card and was secretly wishing he just took me to a shitty Irish pub that wouldn’t have cost me over $100 of my entry level salary.

“It was a birthday present from my aunt and uncle,” he said proudly. “Gotta love meals paid for by gift cards and still having money left over. Otherwise I would never be able to afford this place!”

“Must be nice. I can’t really afford it either but glad you picked somewhere so expensive.”

“Oh sorry! I probably should have asked you if this was OK.”

We exited the restaurant and after a failed attempt at a goodnight kiss I ran for the hills (or subway) and never returned any of his texts.

The Manic Organic

After numerous pathetically failed attempts with the plethora of dating apps on the market, I decided experimenting a new matchmaking service called the DatingRing. Though a bit pricey, I was physically able to meet with a professional matchmaker and acquaint her with exactly what I was looking for in a woman and more importantly, what I was NOT.

The matchmaker showed me a profile of a delightfully attractive young damsel named Sydney and assured me that we would be undoubtably compatible.

Sydney and I evidently had quite a few things in common. We both shared a passion for the outdoors, adopted miniature border collies and enjoyed watching football on Sundays. Sydney sounded like a an extremely suitable candidate for me so I promptly reached out to hopefully begin a courtship.

As usual in the ever-bustling city of New York, our schedules were jam-packed, but eventually we agreed to meet for brunch on a Sunday afternoon.

I arrived at a popular brunch spot in the Jane Hotel 15 minutes early to make sure I secured our reservation. Sydney walked in about 15 minutes late and greeted me at our table where I was already seated.

After exchanging pleasantries the waiter approached us and I asked her if she would like a brunch cocktail.

“Oh, I don’t drink. I will just have a water, please.”

Now, I have absolutely nothing against people who choose not to drink, but most of my social activities (along with everyone else in this city) involve the consumption of alcoholic beverages and often times on an excessive level.

“No big deal. I will have a Bloody Mary,” I said. “Would you like a coffee, tea or anything?”

“No, I doubt any of their coffee or tea is organically harvested. Do you know if your coffee or tea is harvested organically?” She asked the waiter.

The waiter looked at her as if she was on crystal meth. “I don’t know. Probably not.”

I then began to study my menu and asked Sydney if she knew what she wanted to eat.

“I am actually not eating. I am on a cleanse right now and I don’t think anything on this menu is vegan,” she said.

“What about the avocado salad? Will that work?” I eagerly suggested.

“No. I will just have my water. Most of the dressings in salads contain some kind of animal bi-product.”

“Oh, I’m sorry. I wish I had known or we could have done something else besides getting cocktails and eating, brunch food,” I remorsefully replied.

After 20 minutes of spouting off about how consuming only organic, gluten free, non GMO nutrition and abstaining from alcohol will lead to a much healthier physical being, I scarfed down the rest of my chorizo eggs Benedict and tertiary Bloody Mary, and I decided I’d had my fill in more ways than one.

As I attempted to say my goodbyes to Sydney, she invited me to grab a coffee at Starbucks.

…Because I am sure that is ‘organically harvested.’