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On Dating : The Breakups - kale & cigarettes
On Dating : The Breakups

On Dating : The Breakups

I’m on the phone with Ashley talking about how to break up with Erica.

“I just don’t know how to phrase it.. Listen, I have something tough to say…I like someone else. Or, I don’t see a future together…?”

“No, wait. I got it. It’s from all my years watching The Bachelor. You tell her that unfortunately you just have a stronger connection with someone else and you have to follow your heart.” 

“I can’t say ‘stronger,’ I have to say something that doesn’t make her feel put down.”

“But she is getting put down. Can’t you just text her?”

“I don’t think so.”

When Alexis and I decided we were going to be together I was still talking to someone who lived in Houston. We met on Instagram (she was a friend’s sister) and then she flew out to stay with me having never met in person. It went well considering. We sat on my floor talking and eventually I asked if I could put my hand on her back. Then everything changed. 

I liked her. We got along well. I thought about strange things like a nice, content life with her. Buying a house in Jackson Hole and shit like that. Then, Alexis came around. And her affection was so potent I didn’t even think twice before picking up the phone.

“Hi. I’m really sorry to do this. I really, really like you. Honestly. But there’s this person. We’ve been friends for years. And she has kinda always been the main goal for me. And she finally wants to be together. So I have to stop talking to you.”

“Wait, are you serious? I’m falling for you. I feel like I should fight for you right now.” 

“I don’t think you should do that.”

“So, what then?” she asked.

I thought for a moment.

“I think you should assume we are never going to talk again. So whatever you have to say you should say now. I’m sorry.” 

I wanted to tell her the truth. So there was no doubt. I hate not knowing.

Some of my friends told me that was a bit brutal. That stuck with me. 

I left to see Erica. 

We met off the L and walked to Times Square and transferred to the 2,3 to get to the UWS. 

She ate pizza while I watched the theatre line wrap around the building. We’re going to get terrible seats, I thought. Then she gave me a bite and I felt better. 

Inside, we found seats up front. We watched Phoebe-Waller Bridges 80 minute solo performance of Fleabag. I almost fell asleep 3 times. Not because it was boring but because I have been living so many lives lately and needed to rest. 

She wore tights and a reasonably short black skirt with a loose red sweater. Her hair was down and wavy and her cheeks had more blush than usual, probably to pick up the red from her outfit. 

She smiled often and seemed gleeful and youthlike being around me. 

I was more removed. Smiling and talking but not touching her. If we didn’t kiss then I wouldn’t be cheating on Maddy.

I was explaining to Jenny before going out that I don’t actually think it’s possible to like two people at the exact same time. Just like it’s not actually possible to multi-task. It always rotates back and forth depending on the moment. There might be multiple people in my orbit but at any given second I am only thinking about one of them. And that was clearly going to be Maddy.

After the show, Erica and I walked back to the train and rode in silence. I was hoping that my body language would prepare her senses for what was coming. 

We stood there, at 11th and 1st, waiting to say goodbye.

“Is everything okay?” she asked me.


I told her I was not completely over my divorce and still dealing with some frustrations about the settlement. That I wasn’t ready to be invested in a new relationship and that she should know where I was at.

She asked if she should wait a little bit. I nodded my head no. She registered, cut me off emotionally, and turned to walk into the subway to finish her trip back to Brooklyn.

I imagined that ride home for her.

The divorce stuff wasn’t a lie. I had gotten an email from a random lawyer saying my ex-wife was requesting an additional $87,000 immediately in order to settle the case. 

We had never spoken about this. Not once. Our last communication regarding the settlement was through the mediator and everything was in order, just waiting for her signature.

That signature never came. I heard through a friend that she needed to find her voice. And, interestingly enough, she did so without saying anything herself. 

I texted her to get ready for court. The deal was off.   

Ending things with Audrey was a lot easier. We had only been on one date. And even though I kissed her, we were total strangers. 

I wasn’t planning on our last call being our last call. It came a few days before I slept with Maddy for the first time. 

I had left her a message earlier in the day. She called me back around 8:30 that evening. “Hey,” I answered with the grin I sometimes get. 

We were talking about her work. I have learned the importance of asking questions and listening well. Then she started telling me about her appointment at the dentist. She explained it in much greater detail than I was used to. She used some specific medical terms. And it dawned on me that this was a thing people in the medical profession did. It was like being at a bar in D.C. and hearing interns talking about the inner-workings of the President’s mind. I started to lean towards not being interested in her performance of knowledge.

“At one point, I hadn’t been to the dentist in 9 years,” I told her.

“Wait, are you being serious?” she asked.


“Why would you wait so long?” She listed a number of things that could be building up in my mouth and causing horrible problems for me.

“I just don’t care for the dentist. And I’ve always had good teeth. Plus, I can fix cavities with my mind.”

“Okay, that’s ridiculous. You could’ve gotten gum disease.” 

“I don’t think that would be likely given I am in relatively excellent health across the board.”

She was chafed by this. Her oath to always be a know-it-all when it comes to health was being challenged. And I could feel myself gently crossing the line with her, and liking it. 

We were still laughing a little though. It was still moving along. Until we started talking about birth control.

“Yeah, I hate condoms,” I said. The same way I say it to everyone. And usually they laugh and agree. Because, everyone does hate condoms.

“Oh. I use them all the time. Correction, 100% of the time,” she responded. 

“Oh wow. In a lot of ways I would rather just jerk off than have condom sex.” 

“That’s great. Talking to a potential sexual partner and now I can imagine him with Lubriderm and porn when we are having sex.” 

Then I told her I believed I could detect STDs in someone’s aura. At that point I had gone too far. 

“I feel really uncomfortable right now,” she said. 

Something in her was beginning to unravel. I changed course.

“Look, I totally get it. You should always be safe. I didn’t think it was such a big deal. I was just messing around. The truth is that I don’t sleep around. I never have sex with someone unless I know them and see a possible future together. I get tested for STDs between every partner and ask the person I’m going to sleep with to do the same. If I’m sleeping with someone, it’s usually to the point where condoms don’t feel necessary to either of us.”

“That’s because you don’t have to worry about anything. Men are asymptomatic for most STDs. And women walk around carrying HPV and have to worry about cervical cancer.”

“Okay, you’re right. It’s a serious thing to you. Thanks for letting me know.” I was softening because her voice was becoming something else.  

“I don’t think this is going to work. I feel weird. We have way too many differences,” she continued.

“I think you’re right. I’m sorry that I set you off. I thought we were joking and then it took a turn. I agree that it’s completely unfair that you have more to worry about. I respect your approach. It’s just not mine.”

“I’ve got your number. And I kind of know where you live. So, maybe we’ll talk some day,” she concluded.

I chuckled and said okay and we hung up. In the end, nothing could be worth the price of condom sex.  

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