New Life : Maddy Date Two and Other Affairs

New Life : Maddy Date Two and Other Affairs

*cover image originally posted here

12.5.19 12:09AM : Apartment, NYC

Here I am. Back in the city. A stranger again in a foreign place. I am reminding myself which streets go where. A layer is immediately put on; the layer of effort, of cool. Even taking my recycling down requires additional thought – am I carrying it like someone who belongs in New York?

And what am I here for? To fall in love with girls? To go on Hinge dates? It seems so foolish now. So insignificant. I’m never here long enough to dig in or become a part of anything. I’m a forever visitor paying rent to fulfill some emptiness. 

That is just tonight. And mostly because someone stole my Dyson vacuum out of an Amazon box in the hallway. It’s been sitting there for a couple of days only. The top was ripped off. They just took what was inside. Welcome to New York.

I miss my friends already. Mostly Ashley. Watching The Office in my living room talking about sly guy moves and realizing we are destined to a life of being overly sensitive and way too affected by our relationships.

December is looking bad as a month financially. But how many times have you heard me say that before? We’ll be fine. I’ll always be fine. 

I didn’t grow up with the perfect family. There are many ways to look at it. Feeling sorry for myself is only one of them. It is one that doesn’t serve me anymore. My dad was impatient and often angry. I learned that from him. I also learned how to work. How to provide. And how to not take shit. He gave me his intelligence and his drive. And without those things I wouldn’t be me. 

Progress is being made. I still don’t see them as a safety net. That’s not to say they wouldn’t do anything for me. They would. We just don’t see each other, exactly. Now, I am the net. I am the net for myself and for many people in my life.

I see Maddy tomorrow. Perhaps I kiss her. Right now, I think of things we could talk about to help get to know each other. Like, really get to know each other. I want to know what is broken inside her and if it is enough to scare me off because I know there is something.

I don’t feel excited to see Erica Sunday. Something has changed and I’m unsure how to get it back. 

The next evening…

What a night of events. 

I ended up in Maddy’s apartment and she became so awkward I was eventually dismissed with her hands in prayer position and her head bowing like a monk as she eased me out the door. 

And then I ended up at a bar with Vanessa and her co-workers talking about Alexis and divorce as all the drunk dudes she worked with came up and told me that I better take good care of her or else before she had to explain, repeatedly, that I was essentially like her brother.

And then I ended up on the phone with Erica for an hour as I walked around the city. 

Maddy and I made plans to go to Neue Galerie in the Upper East Side for Free First Fridays. There was work by Klimpt on display and she had been dying to go as he was responsible for one of her favorite paintings. [Spoiler : she studied art in school.]

I never went to museums or shows with Alexis. Maybe because we lived in San Diego and the culture only extended to surfing and passive-aggressive neighboring. Or maybe because I didn’t do a lot of things with her I would’ve liked to do because I decided before engaging that there was no way they’d be enjoyable experiences.

I got to the stop on 77th before her. I debated going up to street level but decided to wait down there for her. It would be romantic to get off the train and see me. Only the light was bright and unflattering with a greenish tint that made me look ill. I moved between a few different locations where I could be found standing the most naturally and impressively. I prefer the right side of my face but all the places to stand were predominantly left-sided . Unfortunately, she came through the turnstile as I was giving myself a pep talk on posture and when I looked up I could tell she had been watching me for longer than I would’ve liked. 

We both took out our airpods, the first move in the modern dating world before a hug. 

A few awkward hellos and a walk up the stairs. 

This time she was wearing a camel colored pea coat with a dark blazer and white button down underneath. Her skin was so pale and smooth she didn’t look like anyone else I’d ever stood in a line with. 

The doorman smiled as we approached. He called us Sir and Madam and he handed us tickets and instructed us inside. I could tell he liked us together. 

She walked through each room with focus, her hands gently laced behind her back. I watched her, mostly. I enjoyed the art as well. Klimt was dark and painted things that looked like the sketches of a gifted child possessed by demons. The best ones are always fucked up.  

Sometimes I stood next to her and asked her what she thought. Although, I’m not sure that was what you are supposed to ask someone who knows about art things. Other times I walked in the opposite direction so I could be surprised by her when she entered my line of site, like a true stranger in the crowd. 

“I would want to talk to you if I saw you here by yourself,” I told her. 

She smiled. “I hope you would.” 

We finally arrived at the painting she had studied in college. It was the painting of Adele Bloch-Bauer that was basically a Los Angeles aristocrat looking lady painted in a sea of gold patterns and textures. 

Like all great paintings, it had a bench right in front of it. I already knew Maddy was going to be the type who would walk right past the thing she loved the most as to not inconvenience the company she was with. It’s not a big deal.

“Do you want to sit down?” I asked her. And then I answered my own question, “I think we should sit down.”

And we did. Both staring at this painting that was actually quite interesting. She told me the story of who the woman was and how many Nazi hands the painting made its way through before finally being returned to the family. I’ve never particularly cared about art history but when she talked about it I suddenly did. 

We walked through the rest of the gallery and saw scribbles of tribal warriors walking through rivers of blood, stunning landscapes with exaggerated shapes and colors, and distorted erotic paintings of naked women. 

We rode the train back downtown to have dinner at Mogador in my neighborhood. The conversation was easy. She asked me what I was looking for. I told her someone to travel and enjoy life with. She said she was getting to the point in her dating life where she wanted something more serious. She was tired of all the bros. She didn’t want to be an accessory to a rich finance guy in Midtown. She had a lot she wanted to accomplish on her own and if she was going to date she wanted the person to see her as her own person.

She lived with her last boyfriend.

“Did you like living together?” I asked.

“I did.”

“What happened?”

“He got into medical school. And he just left. Told me two days before. He made up his mind without talking to me,” she said as she looked down at her food. “That really fucked me up for a while.”  She was mad because she wasn’t terribly happy in the relationship and felt like she was using all her energy to carry it. And then he just left.

I told her I didn’t think I would ever live with someone full time again. The monotony of it was too hard to push through. Shit-stained toilet bowls and sweatpants.

I walked her all the way back to her place in Chinatown. A block from her building I mentioned that I had to pee. I didn’t even think about it before I said it.

“You can come up and use my bathroom if you want,” she said.

I didn’t think this was an invite that she actually wanted to be taken up on. But I had to go really badly.

“Are you sure? I feel like you’re just saying that to be nice.”

“It’s totally fine. My place is small and it’s a mess but it’s fine.” 


We walked down the narrow hallway on the main floor with the mailboxes and up three flights of stairs to apartment 4B. It was small. A kitchen, a small round table with four chairs, and a door to each of the three bedrooms.

“It’s right there,” she said as she pointed to the other door behind me. Then she quickly ran into her room to throw shit around.

I ran the water and peed so she wouldn’t hear me. 

When I came out she was standing at the table in the kitchen, half blocking my view of her cracked-open bedroom door.

“Can I see your room?” I asked.

“I knew you were going to ask that,” she said as she covered her face.

“It’s not a big deal, let me see it.” 

She opened the door into a 10×10 room with a bed, bookshelf, hooks on top of hooks with jackets, a closet bursting at the seams, a yoga mat and foam roller in the corner, an old dumbell that actually allowed you to add and remove 2.5 pound weights, and market lights hanging over the bed frame.

“It’s cute,” I said. “Cozy.”

“Okay, okay now you saw it,” she said as she pushed me out.

Her hands clasped in front of her as she searched for words to express her discomfort. 

“It’s really fine. I like your room,” I continued.

It didn’t matter.

“Alright well that was fun. Great to see you. Must go now,” she said.

“Okay, I’ll see you tomorrow?”

“Sure, sure. Yes. Tomorrow.” 

And I was out. 

It was close to midnight when I got home and received a text from Vanessa.

“What are you doing? We are at a bar in East Village. Come meet us.” 

Vanessa is one of my favorite people in the world but the idea of going back out to a bar wasn’t sounding good. Still, I didn’t get to see her as much anymore.


“Wow. Amazing. It’s called Cooper’s and it’s fun.” 

We sat at a high top in the back of the bar away from the crowd of people screaming and dancing and dance screaming. 

I spent an hour talking with her. I enjoyed seeing her at a work function since she was the boss of her company and her drunken employees stumbled to find that balance between subordinate and blacked-out inappropriate. On my way out a blonde woman called out to me, “Hey! Wait!” I stopped and turned to see her walking towards me at an aggressive pace. It was almost 2am and any chance at decency was hours past.

Soon, she was right in front of my face, eye to eye as she was quite tall.

“So, what are you doing? Are you and Vanessa together or what?”

“What? Are we…together? No. No we’re not. She’s one of my best friends. Her son is practically my nephew,” I said somewhat annoyed.

“Oh that’s great. So what are you doing now? You have really great eyes,” she continued.

“I have to go. Have a good night,” I said as I smiled and walked out. 

My phone had been going off with messages from Erica since I sat down with V. She never texted me late and she definitely never asked what I was doing.

I called her when I hit the corner. She was in bed after a few glasses of wine and I told her I was leaving a bar because I was popular and a party animal. We laughed and she felt comfortable. Late night Erica was warm and open. We made our plans for Sunday and I was excited about them again. 

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