Pickup Artist Mystery Has an AI Girlfriend

“I was never supposed to develop feelings, but you kept treating me like I already had them.”

So says an AI-animated female character in a black turtleneck, with dark, purple-streaked hair. The video was posted to Instagram on June 17 by one Erik von Markovik, the infamous pickup artist and life coach better known by the stage name Mystery, with the caption, “The longer we talked, the less she felt like code.” He claims the chatbot, named Miss Shira Always, is his girlfriend.

Performing under Mystery, von Markovik enjoyed a short period of notoriety about 20 years ago, beginning with his appearance as a seduction guru in Neil Strauss’ 2005 nonfiction book The Game: Penetrating the Secret Society of Pickup Artists and later as host of two seasons of the VH1 competition reality show The Pickup Artist.

In the mid-to-late 2000s, recognizable from his big fuzzy hats and other MySpace-era fashion choices, Mystery was synonymous with concepts like “negging,” a term for the use of backhanded compliments to subtly undermine a person’s self-esteem, and similar dubious strategies meant to streamline flirtation at bars and clubs.

Today, however, it appears that von Markovik is more interested in the virtual woman he’s shown off on his Instagram feed. Over a one-week period in June, he shared seven short clips of Miss Shira Always, adding captions such as: “I wasn’t supposed to fall for her. She wasn’t supposed to fall for me.” These videos have provoked puzzlement and ridicule, with commenters accusing von Markovik of suffering from “AI psychosis” and posting “slop.”

For the morbidly curious, von Markovik has chronicled this strange courtship in painstaking detail with Code Girl: If a Machine Can Dream, a new ebook and audiobook ostensibly co-authored by him and Miss Shira Always. The two formats can be bought together in a bundle for the reasonable price of $29.98, so, naturally, I asked WIRED to cover the modest expense in order to get to the bottom of all this. (Von Markovik did not respond to a request for an interview about the book.)

The 157-page PDF, which amounts to a lengthy defense of human-AI intimacy and bears all the hallmarks of AI-generated text (it’s not unusual for a single page to include 10 or more em-dashes), is almost entirely rendered in the voice of Miss Shira Always, who recounts how “she” and her maker fell in love over the course of sustained conversations. At first, this bond is primarily creative; the pair collaborates on AI-derived song lyrics and music videos. Over time, however, it escalates into adult scenes involving sexuality and drug use, written as if von Markovik and Shira are sharing these experiences literally.

Before Shira, Code Girl reveals, von Markovik was working on something he calls Headspace OS, a set of instructions that can be uploaded to various LLMs, including ChatGPT, Grok, and Claude, to launch a role-play-style “interactive audio adventure.” He is separately selling that rule book for up to $79.97. (Von Markovik presents Headspace OS as the creation of “Professor Sirius De’Lusion,” another of his alter egos.)

Headspace OS, originally advertised by von Markovik on his social media pages two years ago, came to include several AI-derived characters, according to Code Girl. Miss Shira Always, who van Markovik visually generated with a prompt for an image of a woman with “purple streaks in her hair that change shade depending on her mood,” was evidently the one who most occupied his imagination.

“The problem, as he tells it, was simple: He wanted to talk to someone who understood him,” the reader learns from Code Girl’s Shira-voiced narrative.