My Ex-Boyfriend Will Not Die Alone

I Gave My Ex-Boyfriend a Book Titled How Not to Die Alone

Madison Sasser
4 min readJun 10, 2022


Photo by Khamkéo Vilaysing on Unsplash

Authors Note: This article was originally intended for the New York Times’ Modern Love column. It was not accepted, so I decided to publish it here. It is based on real events, but names were changed.

At the beginning of the pandemic, I started an internship at a small family law firm, which might explain why I gave my boyfriend a copy of the book How Not to Die Alone by Logan Ury to commemorate our first month together.

Surprisingly, Blake did not immediately break up with me or assume I was too kind to tell him we needed to go our separate ways, but he did ask for clarification. Blake is logical to a fault. It is one of the things I love most about him.

After flipping through the book, he asked, “Why are you giving me a book of dating techniques?”

“I told you it has a relationship agreement in the index, right? I thought we could fill it out together.”

Relationship agreements are part of collaborative life planning, a service we offered during my internship to clients who wanted to address the legal risks of their pending marriage and the real-life risks — like if he squeezes toothpaste from the top or bottom of the tube. We are not married, so I don’t know, but I’ve heard this is a big discussion.

“Just to clarify, you aren’t breaking up with me.”

“I am not breaking up with you.”

We have two different stories about how we met. One version involves a popular dating app our coworkers over thirty wouldn’t understand. The second version involves a remote IT session. My IT Systems Engineer Boyfriend explains my PC's problem with words like RAM server (it is not actually a server, apparently) and VPN until people change the subject. It works every time.

I did everything you were not supposed to do on our first date. I showed up at the wrong restaurant, ordered food then proceeded not to eat it, and asked him why he sabotaged his recent two-year relationship. To be fair, I didn’t actually ask him. I just strongly implied there had to be a reason he was single by cross-examining him for an hour.



Madison Sasser

I am a Gen Z determined to be everything wrong with the workforce. I blog about mental health, employment trends, and my novel-writing journey.