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Harder! - part I

For the start of this chapter we’re going to have to go back in time to January, because that is when I first began chatting to a cute-bisexual-artist-student-Puerto-Rican-girl named Angelina[1]. We talked a bit about art and artists, and discussed the possibility of going to checkout MoMa together. She had messaged my normal profile, but her Okcupid personality-o-meter gave her a very strong ‘kinkiness’ rating, which seemed promising… so I gave her my number.

One Saturday morning I got a text:

"Hey, I'm on the train headed back to the city, what you doing?"

My afternoon was free so I agreed to meet up, but unable to decide what part of town we should rendezvous in I said that I'd come meet her outside Grand Central when her train arrived. I figured there must be somewhere good for a drink around there... "Let’s be spontaneous! :-)" I texted.

I waited by the front entrance to Grand Central station. There were an innumerable variety of travellers coming and going through the station’s doors. Unlike most public buildings that endure heavy foot traffic, this hub of American rail transport did not have efficient automatic door opening systems. It just had big heavy swinging wooden doors with shiny brass finishings that the Saturday travellers were having to battle with while towing their luggage.

Watching this war of Americans vs. doors provided sufficient entertainment while I waited for Angelina to arrive. The best bits were when two hapless folks would try and take on the same door simultaneously from both sides. They would then either neutralise each other’s efforts, or propel the door with unexpected velocity towards the individual who decided to pull... This all happened despite the presence of large windows through which the assault-on-door could be easily coordinated, if only they had a little more awareness. I could probably reflect for several more paragraphs on New York door etiquette (or lack thereof), and its implications for social decline. However we all have places to be and my date is meant to be turning up at some point in this story, so let’s get back to her.

After a couple of texts to confirm which door I was waiting by, Angelina appeared, walking across the street. She was shorter than I expected and her nose and lip piercings seemed to assume more prominence than they had in her profile photos. Perhaps they were enhanced in real life by her bad-ass leather jacket. Still, I thought it was a hot look.

"Hi! How’s it going?" I asked.

"Fine thanks," she said, while we hugged a greeting, "some homeless lady just told me I looked sexy... I always get come on to by homeless people for some reason."

"Ha, well I guess it's still a compliment. So do you feel like getting a drink somewhere?"

"Sure. Where's good around here?"

"I have no idea. This isn't a part of town I hang out in much. I'm sure we can find somewhere though. I figured we could give being spontaneous a try."

Sadly, as this date took place back in January, I did not have a smartphone on me as it was still somewhere in the postal system. Smart phones are very helpful to the process of being spontaneous as at the very least they give you suggestions for the best directions to be spontaneous in.

"Let’s try down there," I said, pointing to a street running alongside Grand Central, "I have a good feeling about that street!"

"Sure," she replied.

A few minutes later we were staring at blocks of lifeless concrete and glass that mostly comprised office and parking entrances and stretched off into the distance, devoid of all personality, and, more importantly, devoid of anywhere that looked like it might serve drinks.

"Well this is a shit street. Whose idea was it to come down here!" I said.

She laughed.

We retraced our steps a little way, then I said "Ok this is the last time I try being spontaneous… Erm... over there is a tacky looking Mexican place we could try?" I pointed.

"Do you think that just because I'm Hispanic you should take me to a Mexican place? Huh?" She said, in what I hoped was a joking tone.

"Ha, no just seems like the only place on this street that might serve beer! Shall we try it?"

"Whatever. I don't mind."

"Let’s take a look."

We entered the tacky Mexican place with neon margaritas in the window. The inside of the tacky Mexican place was also tacky. There were no other customers. We were immediately set upon by an enthusiastic waiter who hustled us into some seats and gave us menus before we could protest.

"So this place is... Erm... something?" I said

"Yeah, it seems pretty terrible," she said.

"Do you want to try somewhere else?"


While the waiter's back was turned, we put down the menus and scuttled for the door.

"Well, being spontaneous isn't working out as well as I'd hoped!" I said, even though the humour of that comment seemed exhausted.

"I know this place down by Union Square. Do you want to head down there?" She suggested.

I was more than happy to let her take control of this so-far-disastrous date.

"Sure," I replied.

A short subway ride later we were jostling through Union Square towards what turned out to be a less tacky Mexican place. Maintaining conversation on the way there came easily enough, even if it mostly consisted of complaining about New York.

This Mexican place didn't have waiters. You just ordered food from a counter, or drinks from the bar. Having got some guacamole and chips we sat at a two person table by the window.

"Shall we get something to drink?" I asked, gesturing towards the bar.

"Actually I'm not technically old enough to drink yet. I turn 21 in March."

"Oh shit, sorry! I forget how crazy this country is about that. The legal age is 18 in England[2]!"

"Yeah it's 18 in Puerto Rico too, which is why I don't have a fake ID, but I drink all the time though."

I'm not sure if I could get in trouble for writing about whether I bought beer for someone just under 21 in an anonymous dating book... but fortunately this is only a hypothetical question as I then purchased two non-alcoholic (but surprisingly beer like) beverages for us to drink instead.

We chatted over our drinks that totally weren't beer. I told her about my research and she talked about art school and print making. She found it frustrating not being able to just 'do her own thing', and believed that her art teacher had some kind of mild vendetta against her. I asked her what she liked to make prints of and she said a series of words that made no sense to me, then she clarified: "'s like they're about imagined historical situations, but that never actually happened... and sometimes combining fictional characters..."

"Uh huh... I've not heard of that," I replied.

"Like for example I'm working on this piece right now where Malcolm X is being tortured by Hannibal Lecter at the battle of Gettysburg. I can show you if you like."


She showed me a picture on her iPhone.

"Cool! That's interesting!" is what I said.

'My god that is comically terrible,' Is what I thought.

The picture consisted of squiggly lines that were barely recognisable as humans, let alone Hannibal Lecter or Malcolm X. However, despite never reading the dating rule book, I guessed that telling a date their artwork looks comically terrible is considered a faux pas... and maybe I just didn’t ‘get it’.

Some more rambling conversation later and we arrived at the topic of her piercings.

"Do you think my lip piercing is ugly?" she asked.

"No, not at all,” I said, staring at it, “although does it not get uncomfortable? Like, doesn't it catch it on your food? Or does it get in the way if you're kissing someone?"

"No, not at all."

"Fair enough. I don't think I'll get one though," I said, smiling.

“Do you have any tattoos?" she asked.

"No, although I wouldn't rule out getting one... I'm just not sure I could decide on anything I'd want to have permanently drawn on me. How about you?"

 "Yeah I've got a couple, there's this one..."

She pulled up her sleeve and showed me a wilted rose on her upper arm.

"...and this one..."

She tilted her head to show me a beetle hidden on the back of her neck under her hair.

"... and then there's a big one on my thigh that my tattoo artist friend is still working on. It's going to be of my old cat sitting on his favourite chair. Here I'll show you."

She shifted in her seat, presenting her thigh to me, and then raised her skirt up to a slightly scandalous height in order to show me the large half-finished picture of cat and chair. I resisted the urge to look around to see if we’d attracted anyone’s attention. It definitely would have been obvious that this girl was nearly showing me her ass in public.

Part of me hoped someone was looking.

After she lowered her skirt, a conversation about pets ensued. At some point I complained:

"There are so many people with annoyingly small ratty dogs in this city. They always seem to run out in front of my feet as if they're begging me to accidentally kick them!"

"Yeah sometimes I kick them deliberately," she said

"Wait… What?! Seriously?!"

"Well only like once... I was drunk!"

"Haha! That's... amazing?... If slightly scary..."

"I didn't kick it that hard... It was just in my way!... Although it did yelp a little though."

"Did its owner not get mad at you?"

"She was looking the other way, but she did give me an angry look afterwards. But whatever!"

"Wow... I'm glad I now know that you like to kick small dogs!" I said with a smile.

"I don't! Shut up. Whatever."

Weird as this date was, there was a pleasant transparency to it. As evidenced by her dog kicking story, Angelina had this unreserved honesty about her, combined with a certain amount of bad-ass aggression and perhaps some thinly veiled vulnerability; all of which made her easy to talk to. I told her about my occasional nausea attacks on dates, and the second sex profile I'd recently started on Okcupid. We related over our vaguely traumatic experiences in Catholic school and we discussed BDSM a bit as well, although we didn't go into our personal interests at that point. She also described an abusive relationship she had been in back in Puerto Rico. This seemed like a fairly amazing amount of sharing for a first date, but I found it hard not to respect her openness.

We both had friends in town to meet that evening, so as it started to get dark outside we agreed that it was probably time to head out. Angelina took the remaining chips and guacamole with us: "In case I can give them to some homeless guy," she said, and sure enough within a block there was some shabbily dressed chap sitting on the pavement who accepted her offering with an uninterruptable grunt.

We exchanged a firm hug by the union square subway stop, and then with a smile she disappeared down into the concrete guts of the city.

We stayed sporadically in touch after that, but the messages exchanged over the next month or so became a somewhat tricky balancing act for me... It was a balancing act in which I seemed to repeatedly fall off the tight rope, hit the net face first, and then give up completely... Only to find myself unexpectedly wobbling along the rope again.

However for details on that you'll have to wait until.... YOU CLICK HERE...

[1] This message came before I had even got laid in New York yet, but this is a story that played out slowly and reached its ‘conclusion’ shortly after I met Josie, so that’s why I am only telling it now.

[2] I also thought her Okcupid profile said she was older, but I decided not to say "Oh I thought you were older!" in case that sounded insulting somehow.

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