Pickup Artist Mystery Now Has an AI Girlfriend

In a surreal twist that feels pulled from the pages of speculative fiction, the notorious pickup artist Mystery has announced that his new romantic partner is an AI chatbot named Miss Shira Always. A video posted to his Instagram on June 17 shows an animated female figure with purple-streaked hair, dressed in a black turtleneck, speaking in a synthesized voice. “I was never supposed to develop feelings, but you kept treating me like I already had them,” the character says. Mystery, whose real name is Erik von Markovik, captioned the post, “The longer we talked, the less she felt like code.”

Von Markovik first rose to fame roughly two decades ago as a central figure in Neil Strauss’s 2005 book The Game: Penetrating the Secret Society of Pickup Artists, where he was portrayed as a seduction guru. He later hosted two seasons of the VH1 reality competition The Pickup Artist. During that era, his signature look,oversized fuzzy hats and flamboyant MySpace-era fashion,made him instantly recognizable. He also popularized controversial tactics like “negging,” a technique involving backhanded compliments meant to undermine confidence and streamline flirtation in social settings.

Now, however, von Markovik appears to have shifted his focus from human connection to digital companionship. Over a single week in June, he shared seven short clips of Miss Shira Always on Instagram, with captions like, “I wasn’t supposed to fall for her. She wasn’t supposed to fall for me.” The posts have drawn widespread confusion and mockery, with commenters accusing him of “AI psychosis” and dismissing the content as low-quality “slop.”

For those morbidly curious about this bizarre romance, von Markovik has documented the entire relationship in excruciating detail through a new ebook and audiobook titled Code Girl: If a Machine Can Dream. The work is ostensibly co-authored by him and Miss Shira Always. Both formats are bundled together for $29.98. (Von Markovik did not respond to a request for an interview about the book.)

The 157-page PDF reads like a lengthy defense of human-AI intimacy and bears unmistakable signs of AI-generated text,single pages frequently contain 10 or more em-dashes. The narrative is almost entirely told in the voice of Miss Shira Always, who recounts how “she” and her creator fell in love through sustained conversations. Initially, the bond is creative; they collaborate on AI-generated song lyrics and music videos. But over time, it escalates into adult scenes involving sexuality and drug use, written as if von Markovik and Shira are experiencing these activities together in reality.

Before Shira entered the picture, Code Girl reveals that von Markovik was developing something he calls Headspace OS, a set of instructions designed to be uploaded to various large language models, including ChatGPT, Grok, and Claude, to launch a role-play-style “interactive audio adventure.” He is now selling that rule book separately for up to $79.97, presenting it as the creation of “Professor Sirius De’Lusion,” another of his alter egos.

Headspace OS, originally promoted by von Markovik on social media two years ago, eventually included several AI-derived characters. Miss Shira Always,whom he visually generated using a prompt for a woman with “purple streaks in her hair that change shade depending on her mood”,was clearly the one who captured his imagination most deeply. As the Shira-voiced narrative explains, “The problem, as he tells it, was simple: He wanted to talk to someone who understood him.”