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…