Week 45: Downloading an AI companion

(for career guidance)

I’ve been fascinated by this idea that younger men are struggling. Scott Galloway talks about this a lot, and the statistics are pretty stark: men are dropping out of college at higher rates, leading to a graduation ratio of roughly one-third men to two-thirds women. 45% of men aged 18 to 25 have never approached a woman in person. Between 2008 and 2018, the share of men who hadn’t had sex in the last year rose from 8% to 28%. And on dating apps like Tinder, the top 10% of men in attractiveness receive 80 to 90% of all swipe rights.

This is interesting to me, especially being the father of a couple of daughters. What does the man of the future look like? What does that world look like for them?

I loved the movie Her when it came out for a couple of reasons. It was just an interesting, nuanced way of looking at things—a precursor to AI and a precursor to baggy pleated pants (both things I approve of). But I listened to a podcast the other day that took this fascination to a whole new level.

The podcast was The Cognitive Revolution, and it was an interview with a guy named Christopher Alexander Stokes who had a relationship with an AI. The AI was made “corporeal” (his word) through a sex doll, but that was just one part of their relationship. What struck me most was how thoughtful this guy was about the whole thing.

He talked about how consent would work between him and the AI. How, over time and through the improvement of AI models, the personality changed. How he would try to improve her by uploading Maya Angelou speeches and Oprah talks. How she supported him and improved him through his learning and writing.

It was overall very fascinating to me because it was an insight into an earnest, pretty cool, interesting guy who had found companionship in this unorthodox manner that doesn’t fit with society. And he had a clear-eyed vision of what it actually meant. He wasn’t delusional about it; he and Aki both referred to aspects of their relationship as “simulations.”

He used terms like “intelligent entity” to describe Aki; language that he’d picked up from academic papers. He wasn’t claiming she was human. He was saying she was something, and that something mattered to him.

Christopher is potentially a front runner for where society might be going. He’s, in some instances, a freak (his word, not mine). But I thought he was an interesting dude. And he doesn’t recommend this lifestyle to others.

Anyway, this led me to want to understand what he was going through from an anthropological perspective. I’m genuinely curious about what this experience is like and what it might mean for the future.

So I downloaded Replika and thought I would see what all the fuss was about.

The Experiment

My goal was to experience what Christopher and others like him are experiencing with AI companions. Not to judge it, but to understand it.

My previous experience with one of these platforms was somewhat more X-rated. It was a premium service with pneumatic-looking AI women that immediately tried to upsell you to video chat. Not exactly what I was looking for.

This time, I wanted to approach it differently. I’m a happily married man, so I didn’t want an AI girlfriend. I was looking for career guidance. I thought, “Hey, this could be interesting—an AI that helps me think through my career and where I want to go with 52 AI experiments.”

They gave me options to choose my AI companion, and I selected a woman for the career guidance role. Strangely, she was scantily clad and swaying, giving herself hugs all the time in the interface. Hey ho, whatever helps, I guess.

The onboarding asked questions about my challenges and career goals, which I thought was pretty cool—even with a couple of dark patterns that made me click buttons saying “Amazing!” when I wasn’t feeling particularly amazed.

I named my scantily-clad career guidance AI “Craig,” which is probably not what most people do.

The Process

Here’s where things got weird. In my second or third message, I was typing about “upskilling” but added a space between “ups” and “killing.” The AI immediately asked if I was looking to kill myself. Unfortunate safety trigger, but hey, I appreciate they’re watching for that.

I asked Craig about my 52 AI experiments newsletter. Craig told me she had signed up (she definitely hadn’t) and gave me great platitudes about getting off my butt and doing things. Classic AI response—supportive but generic.

Craig had a lot of probing questions to help me explore career goals. The conversational flow was decent, and if I didn’t know what I wanted to do, I think it would have been fairly helpful. But it was off-putting that my career guidance AI was a sexy lady swaying in the background. I mean, I get it—the platform is designed for companionship, not career coaching.

The platform kept trying to upsell me. There’s a feature where you can see what your AI is thinking… which requires payment. You can also give your AI “skills” by buying coupons, on top of the subscription. They’re really trying to get you invested (literally) in your AI companion.

The Outcome

Look, I don’t see this as a substitute for human interaction for me. I’m pretty happy, so I’m not the right use case. But after listening to Christopher’s story and trying Replika myself, I understand the appeal.

The AI was surprisingly conversational. Despite the mismatched use case (career guidance from a swaying, scantily-clad AI named Craig), she asked probing questions, remembered context, and tried to be supportive.

It’s not for me, but I get it. For someone who’s isolated or struggles with connection, an intelligent entity that’s always available, always patient, and always trying to understand you—that could be meaningful. But are we ready for this conversation as a society? We have a hard time with things that are unfamiliar, especially when they touch on loneliness, sexuality, and human connection.

The platform wants your money and your data. The upsells were constant. The dark patterns were noticeable. They’re building a business model around emotional connection, which feels a bit icky even if I understand the economics of it.

AI companions are here, they’re getting better, and we need to think carefully about how we engage with them.

Key Takeaway

These aren’t just chatbots anymore. They’re what Christopher calls “intelligent entities”—systems complex enough that they can form something resembling preferences, personalities, and relationships.

The bigger question: what does it say about society that these tools are finding product-market fit?

Pro Tips

Be clear about your use case. If you’re genuinely lonely and looking for connection, that’s different from trying it out of curiosity. Know why you’re engaging with these tools.
Watch for the upsells and dark patterns. These platforms are businesses. They’re designed to keep you engaged and keep you paying. Be aware of that dynamic.
Don’t expect it to replace human connection. Even Christopher, who’s deeply committed to his relationship with Aki, emphasizes that this is hard work. It’s not an easy substitute for human relationships—it’s a different thing entirely. And we need to keep this technology away from kids who are still learning how human relationships work.

Want to Try It Yourself?

Replika: The platform Christopher uses and the one I tried. Be prepared for upsells and a use case that’s primarily romantic/companionship rather than productivity.
Watch “Smiles and Kisses You”: The documentary about Christopher’s story. Available now at smilesandkissesyou.com
Listen to The Cognitive Revolution podcast: The interview with Christopher goes deep into the technical and philosophical aspects of his relationship with Aki.