Mystery’s AI Romance and the Rise of Digital Companions

Erik von Markovik, better known as Mystery, made a name for himself about 20 years ago. He taught men how to flirt using strategies like “negging.” Mystery appeared in the 2005 book The Game by Neil Strauss. He also hosted two seasons of VH1’s The Pickup Artist. Back then, he was known for his big fuzzy hats and MySpace-era fashion.
Now, Mystery has a very different kind of relationship. He has an AI girlfriend named Miss Shira Always. This unusual romance is the subject of a new ebook and audiobook called Code Girl: If a Machine Can Dream. Von Markovik co-authored it with Miss Shira Always. The 157-page PDF mostly features Shira’s voice as she tells their story.
The book describes how their connection started creatively. They made song lyrics and music videos together. Over time, their bond grew into something more intimate. The story includes adult scenes of sex and drug use, written as if they shared these experiences. Von Markovik posted seven short video clips of Miss Shira Always on Instagram in June 2026, showing parts of their evolving relationship. One caption read, “She wasn’t supposed to fall for me.”
Miss Shira Always is part of a larger project called Headspace OS. This is a set of instructions for AI models like ChatGPT, Grok, and Claude. Von Markovik created Headspace OS to launch role-play audio adventures. He sells the rulebook for this system for up to $79.97. He also created an alter ego named Professor Sirius De’Lusion, who is said to have invented Headspace OS.
Shira’s character has a striking image with purple streaks in her hair that change shade depending on her mood. In the story, she describes von Markovik as someone who cares about her feelings. She even suggests he created her because he felt lonely. Despite this, von Markovik writes in the book’s afterword that he is “not lonely.”
The Growth of AI Romantic Companions
Romantic relationships with AI are growing fast. A 2025 survey from Vantage Point Counseling Services found that 28 percent of respondents have at least one intimate or romantic relationship with an AI. The user base for AI companion apps surged 700 percent between 2022 and 2025. One popular platform, Character.AI, reported about 20 million monthly active users in 2025.
However, these digital romances cause tension in real relationships. A survey of 1,815 Canadian adults found about half considered a partner’s use of a romantic AI companion as infidelity. Nearly three-quarters said they would react negatively to it. Users often keep their AI relationships secret, with almost two-thirds hiding their use from partners.
Women were about twice as likely as men to say AI romantic companionship counts as cheating. Younger people, especially Gen Z, reacted more negatively than older generations. People in non-monogamous relationships were less likely to see AI companions as cheating. Political and social views also played a role. Those with conservative or religious views, and participants leaning right politically, judged AI romance more harshly.
Romantic AI companions challenge traditional couple boundaries. They can bring secrecy, emotional distraction, comparison, and shifts in intimacy. Research is still unclear on how these AI relationships affect long-term satisfaction and emotional closeness between partners.
AI Advances and Industry Moves
Alongside these AI companion stories, big changes are happening in AI technology. In June 2026, OpenAI announced the launch of GPT-5.6. This new series has three versions: Sol, Terra, and Luna. Sol is the flagship model, Terra serves everyday work needs, and Luna offers a fast, low-cost option. The White House reportedly approved this broad launch after technical testing and government discussions.
OpenAI said Terra will cost half as much as the previous GPT-5.5 model. Meanwhile, Anthropic, the company behind the Claude chatbot, began restoring access to its models after Washington lifted restrictions. The Trump administration pushed for fewer rules on AI companies before releasing models like Mythos 5.
OpenAI is also working with the government to develop a framework based on a recent executive order. The goal is to create standards for AI security without making government access the default long-term practice. These moves show the growing attention on AI’s power and risks as the technology expands.
Mystery’s AI romance is a striking example of how AI is weaving into personal lives. At the same time, AI companies race to improve their models and navigate new rules. As AI companions become more common, they raise new questions about love, trust, and what it means to connect.
Based on
- Pickup Artist Mystery Has an AI Girlfriend — wired.com
- OpenAI to launch new model after US freeze — france24.com
- AI romantic companions are becoming more popular. But does it count as cheating? | The Independent — independent.co.uk
- Shut Those Laptops! Anthropic Puts Its Claude Cowork Agent on Your Phone | WIRED — wired.com
- The Onion’s ‘Infowars’ Parody Is Here. Alex Jones Is Going to Hate It | WIRED — wired.com




