writing – Shady Characters

The dash for AI

August 29, 2025

There is a new AI controversy in town: chatbots are ruining the em dash.

Over the past year or so, a number of people have decided that texts created by generative AI applications contain more em dashes than might otherwise be expected. The complainants come from LinkedIn,1 Reddit,2 Instagram,3 and beyond. There’s even a thread on a forum operated by OpenAI itself,4 the company which owns ChatGPT, whose participants bemoans the bot’s excessive and apparently unstoppable use of em dashes.

Backing the backslash

March 14, 2025

I’m almost ashamed to say it, but I never really gave the backslash a second thought.

The backslash’s forward-leaning counterpart is everywhere, especially in computing. It lives in network and web addresses such as https://shadycharacters.co.uk; in file paths, such as /home/keith; and it introduces human-readable “comments” in any number of programming languages, often like /* this */ or // this.

Miscellany № 105: blog questions challenge

January 31, 2025

There is something interesting happening with blogging. For a long time, blogs like this one were the way to opine, to share, to bloviate. Then social media came along and stole blogging’s thunder, with the average blogger gravitating towards long threads on Twitter (RIP; † ⚰; 💀; etc., etc.) or photo-heavy Instagram posts. Next came newsletters — blogs delivered by email, essentially — which finally broke the social media hegemony.

Bombs, books and generative AI: a blunt and obvious parable

November 9, 2024

I know, I know; these days, everyone and their five-legged, three-eyed dog is writing a piece about AI. I can’t promise that this one will be more insightful or educational than any of the others, but I can promise that it will invoke humanity’s undimmable hubris, the atomic bomb, mad cow disease, and, to keep us on brand, books.

Shady Characters at MacGuffin magazine: interrobang!

January 4, 2024

The following was published in issue 13 of MacGuffin Magazine. It recapitulates some of the contents of my interrobang series and adds some new details to boot. Enjoy!

The Speckters lived in a postwar apartment near Gramercy Park in Manhattan. Their collection of printing presses lived in a rented apartment across the hall, a three-thousand-pound Columbian press balanced carefully across the beams under the floor. The couple were steeped in the world of printing: their kitchen hosted what they called the “Four Penny Press”, and their apartment(s) were visited by a parade of typographic celebrities such as Hermann Zapf and Steven Saxe.