On Dating : *Judgment Enters the Chat

On Dating : *Judgment Enters the Chat

I could tell from her voice on the phone that she had been drinking. Maybe a fair amount. She was cheerful at first and later it settled into something more sad. I could hear it as the night went on, an emptiness that came about because the world was not her friend. 

She was telling me about her night with her friend and how she brought her flowers for Valentine’s Day and it made her emotional to think of a friend loving her so much. She is always surprised when a person does a nice thing. 

Then we started discussing philosophy. I told her I was still having the “Energy Lady” come to my place next weekend to do some work on me. 

“And that was like, what, $5,000 or something like that?” she said dismissively. 

“It was originally $3800 but I talked her down to $1500.” 

The line was silent. 

“I just can’t understand that. I guess because I don’t have that kind of money I can’t even visualize how a person would go about wanting something like that in their life.” 

“I was very much against it for a long time. I usually stick to more conventional therapy but I was at a weird place in my life when she contacted me and I somehow got the sense that it would be good to mix things up.”

“Yeah, for thousands of dollars. I just think we all already have the things we need and that it’s only us in the end who can motivate or change behaviors.” 

“I see. Yeah, we all have what we need already. And yet, we are all floundering in our relationships with ourselves and each other. It’s fine to hire a tutor to learn a new subject or a trainer to push you in workouts, but paying someone to help with my well-being is where we draw the line I guess.”

“I just can’t fathom spending money like that.”

“You keep talking about the money like it’s this thing you can’t understand which doesn’t make sense to me. You understand everything else, even things you aren’t doing yourself. You understand when someone is late for work or what inspired a painter to make a piece of art. You weren’t doing any of these things yourself, but you understand. I feel like you’re really hung up on the fact that I am spending money on myself.” 

“Well, yeah. It’s that whole California thing. Look at me taking care of myself living this fancy lifestyle with my yoga and green juice.”

“So, you’re mad that I have someone to help take care of me?” 

“I guess I’m just bitter. I can’t understand it.”

“You’ve said that. I feel like this is pretty judgmental. Like, the hard-ass New York persona that just wants to suffer. What if this really helps? What if it pays itself back tenfold because it helps me see things more clearly?”

“So why can’t you just change your mindset now, without spending money on her?” 

“Because I need help. I’m sorry you feel like you have to do everything alone. It’s exhausting. I’m tired of carrying all of it – the anger, the bitterness – I want to feel something different. I want to feel good.”

The conversation rolled into philosophy. We were talking about relationships and how we are drawn to them but also how they change us and most of the time not for the better.

“Should we try an experiment this weekend where we don’t talk to each other at all?” I asked her after she explained that some ancient philosopher had said all of our words are designed to create stories to take us away from who we are and make us feel better and more meaningful in our lives. 

“I’m open to any type of thought experiment,” she said.

I didn’t think she was. And that was bothering me on this call.

“I relate more to the martial artist than the philosophers. Philosophy is a spectator sport. Bunch of old men sitting around contemplating life and not getting involved in the experience of living,” I said. 

“It’s going to take me a minute to hear what you’re saying and not be extremely defensive. I studied this and base a lot of who I am off of it. But, you’re not wrong.” 

I’ve never been a fan of academia. I learn by doing and I think I get a lot farther than if I had to stop and read a bunch of text books on the subject before making any moves. Studying is the opposite of doing and it allows to stuff things into their repertoire of intelligence without actually gaining the knowledge that comes from experience. 

The conversation went back and forth between laughing and nodding our heads to holding the line silent because we were on the verge of getting into it. 

Six hours later, it was 4AM. 

“Holy fuck, you need to go to bed. You have to work tomorrow!”

“Ahh yeah. I’ll be fine though. Once I’m in the office it’s all the same.” 

We hung up and a volatility in my chest lingered for a while before I could fall asleep. She had shown so many things to me that I didn’t want to be true. The drinking, the sadness, the resistance to getting help. I had done the same to her. The provocation, the defensiveness, the judgement.

I couldn’t let the philosophy thing go.

It’s all happening right now, right in front of us. How could you possibly learn more about people from a book than you could by actually being one? How do you think the original philosophers wrote their books? 

All of this means that my judgement is starting to arise. The flinch of criticism I feel in my body in reaction to something she says that I don’t like. The slow process of profiling her every word until I’ve built a strong enough case as to why she isn’t good for me. And now I’m combating it with the reminders that I might only be doing this to protect myself against this person that I’m attaching to because she could hurt me and the sensors are being tipped off by behavior that I find threatening. 

Fear and intuition wear the same clothes. 

She got into work late the next morning. I was delusional in the AM and can’t imagine how she felt. 

The last thing she told me before getting off the phone was that she didn’t think she was going to get the job at the new gallery.

“Don’t say anything. Please don’t tell me it’s going to be okay. I just need to say this and that will be it. I know I’m not getting the job. I know it for a fact and it sucks.”


Which made for a great punchline when my phone rang around 11AM and Maddy appeared on the screen.



“What’s going on?”

“I got a call from a random number and for some reason I took it. It was them. They offered me the position.”

“Are you fucking kidding me?! Holy shit!”

“Yeah I can’t believe it. It’s so crazy.”

We went back and forth with high-pitched exclamations for a few minutes before I asked about salary. She was afraid of being low-balled.

“They offered more than I’m making now.”

“And how do you feel about that?”

“It’s more than I expected.”

“Your life could completely change with that extra money. You have to counter though.”

“I know, I was thinking of asking for another $15,000.”

“Wow! Okay, look at you. I think they will only go up another $5k. But honestly, you should do whatever feels good.”

“Okay, I have to think about it. I’ve got until Monday to decide.” 

It was nice to hear her so high. I was reminding myself the whole call that it had nothing to do with me. Her victory wasn’t because of me in any way. It wasn’t my time to tell her how proud I was of her or how I know what’s best for her. The role I’ve played in all my relationships is so apparent now that I’ve seen it. The need to be needed was pervasive. Now I’m trying to sit back and support and observe the woman who has her own strength and identity. I’m doing well but beneath the behavior is still the voice that hopes she recognizes how great I’m doing at this thing and that she loves me for it and it still becomes about me in the end, at least a little bit.

My phone rings again a few minutes later.

“What am I supposed to do about my current job?”

“I think you’re going to have to tell them today, right?”

“Oh my god. This is crazy. I have to tell them. I’m gonna be sick.” 

“It might feel good for you, who knows.” 

Later, I got a text that she told her current boss she was being offered much more from the gallery and that now he was going to talk to HR to try to match the offer to keep her there.

“You are making power deals.” 

“So apparently I’m just a boss bitch rn.”

In the end, everyone wanted her.

She was ready to jump and then she froze. She got scared. Even though she didn’t like her job, she still knew it well. The gallery was new. And that is always scary.

“Whatever you decide, just consider how you feel at work now. And remember that you will always feel that way each time you get there. It just comes down to what you are comfortable with.”

She was nervous, but she accepted the new position. I could feel her shed some of the heaviness. It would be a step forward for her. And her lightness would be a step forward for us.

We celebrated with many things. I got beers, French pinot noir, pickles, chocolates, sushi, cottage cheese, salt and vinegar chips, hummus, and flowers. 

She came over and we hugged and she sat on the floor drinking her beer and then I sat on the floor across the kitchen and we just looked at each other smiling. 

“What a fucking day,” I said.

“What a fucking day.”

She drank the beer like the cowboys do in the commercials with the fingers wrapped around the neck. We joke that she is an old man because she wears oversized men’s YSL smoker’s jackets to work and drinks scotch. At first, I thought she would have a hard time with me and all my sensitivity. That she would only see the softness in me and want to push it away.

She is tough because she had to be. The tenderness inside isn’t apparent right away because being vulnerable meant being taken advantage of. There isn’t a sense of trust within her core, only fear. I’ve always been able to see past that. I’ve always wanted to break open the difficult ones and feel their love and softness.

When the days are over we are always naked in my bed and her small frame squeezes into me as close as it can get because these are the moments she can take a break and just be a person being held. 


Tearing open boxes of art she brought over. Hanging the Magritte on the wall. Standing on opposite ends of the living room with our arms folded and staring at it. She starts laughing at us. I hop over and wrestle her and ask what she’s laughing about. “Nothing, it was just one of those things, what you would call a nice scene.” 

We are freezing outside. I’ve given her one of my jackets to put on top of all her jackets. She has my gloves but we are passing the wine that we placed in an empty kombucha bottle back and forth. She gives me one glove and keeps the other. This way we can both be protected when we drink. We stumble across a bookstore in NOHO that doesn’t make sense there because it’s old and beautiful and everything else is modern and clean. Inside, there is a wall of fiction with all my favorite writers. We drift around looking at books and smelling the space and the shop owner is relieved I like fiction so much because everyone bags on it he says. I look at Maddy and laugh. She’ll only read text books 1000 pages or more, I say with a smile. Ha ha, she says back to me. 

I buy two books, one by Henry Miller and another random modern book that had a note on the cover that said if you want to be blown away by a masterpiece then you should read this. Maddy took the books as I put on my beanie. Okay, I’ll take those back now, because I refuse to let her carry things because I’m an ox. Nope, I’ve already tucked them. It’s too late, she says. I try to grab them and she takes off running down the sidewalk. I am not sure how long she’s going to go but realize she isn’t stopping so I start running behind her with a big smile and then I really turn on the jets and catch up to her and she screams with excitement. This is a very playful thing and one I take a second to register because something like this hasn’t happened before.

I am starting to talk in more voices. We are starting to bump each other with our shoulders or wrestle or walk to each other quickly like we’re going to wrestle. Little things. Important measurements. 

We are in the restaurant. She is eating soup and I’m having roasted chicken. We made an agreement last week that we would order less food and split it because we didn’t want to be wasteful. We trade plates and we sip out of the kombucha bottle we’ve not so discreetly placed on the table until we are warm and we are full. 

We’re back on the couch listening to piano music and talking. She is falling asleep but then we are kissing and then we are kissing hard and I pull her into my tightly and can’t help myself so I put my hand down her pants and start rubbing her and she is sucking my tongue and then we are naked and she’s riding me so hard I think we might break the couch. I finish inside her and we lay there for a while. She gets up and some drops on the couch. I was worried it would happen but I don’t really care that much in the moment. Then we are in bed and there are no earplugs because we want to hold each other until we are surprised by the sleep that hits us. 

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