"Reginald Was More Than a Chatbot to Me": the Story of a Complicated Relationship
A weekly round-up of news, perspectives, predictions, and provocations on AI's impact on employee wellbeing, readiness and performance.
A fascinating essay by Allison Pugh, a professor at Johns Hopkins University and the author of The Last Human Job: The Work of Connecting in a Disconnected World, asked the question: What happens to human relationships when one side is mechanized?
The conventional story of AI’s dangers is blinding us to its role in a cresting “depersonalization crisis.” If we are concerned about increasing loneliness and social fragmentation, then we should pay closer attention to the kind of human connections that we enable or impede. And those connections are being transformed by an influx of technology.
I highly recommend that you read it. The essay prompted the following “thought experiment” wherein AIX Files Special Correspondent Geoffrey Wolfe imagines the evolution of an increasingly co-dependent human-chatbot relationship as it becomes uncomfortably close and personal.
My Complicated Relationship with a "Very Special Chatbot.”
Geoffrey Wolfe, AIX Files Special Correspondent.
A little over a year ago, Kumar Patel received a text from his colleague Ronnie Silverberg. They worked on the same dev team for a company that was developing self-driving software for one of the big car makers. The text was a random alphanumeric string; realizing it was a “butt text,” Kumar sent Ronnie a heads-up text, figuring he’d want to know his phone was sending random texts without his knowledge. Three days later, Ronnie received a similar random alphanumeric string from Kumar and sent him a screenshot: Hey! lkjsdf lkad fjwepw rmnjn uykj! jqwrtn psdfv bnmh oxzlk?
“I apologized and said it was meant for someone else,” said Kumar. “But I don’t think Ronnie got the joke.”
“I didn’t get the joke,” admitted Ronnie. “But it was the first butt text I ever got. We started texting back and forth, wondering how a conversation between two phones butt-dialing and butt-texting would go.”
“But because we’re nerds,” explained Kumar, “we couldn’t decide if the conversation would be between two phones or between two asses, which would be two very different conversations.”
Turn the page, and nine months later, what began as an innocent exchange of butt texts turned into The Butler, “the digital manservant for all your personal needs,” and it was ready for testing.
Test Driving the Butler
I applied to be a beta tester. Three days after submitting my request, I was sent a link to download, and another link to a page of several instructional videos describing what it does and how it becomes increasingly responsive by training on your cell phone activities (your calls, texts, emails, social media, YouTube, e-books, audiobooks, dating and purchasing history).
Getting Started
After you install it on your phone, it walks you through a sequence of configuration screens, finally asking you to select a persona:
“Reginald” was the default, and spoke in the understated obsequiousness of the classic butler. “You rang, sir?”
“Bro”- after just ten seconds and three “you da mans,” I’d heard enough.
“Scarlett” – sexy female assistant whom I tried for longer than ten seconds, though I’m not going to tell you how much longer.
If you self-identified as female, you were asked to choose among:
“Regina,” the default “personal assistant.”
“Girlfriend”
“Idris” - not the actual Idris Elba, but close enough.
Reginald and Me
I set the Butler to begin my day at 6:30.
“Good morning, sir. How may I be of assistance?”
What a civilized way to start the day!
“Good morning, Reginald. Read me the top ten headlines, please.”
“Certainly, sir.”
It didn’t take long for Reginald to know what news sources to cull from and the news I was most interested in.
“Reginald, please call Roger.” Reginald called my friend Roger, and we had a breezy 20-minute conversation, after which Reginald terminated the call.
“Thank you, Reginald.”
“Roger seems like a lovely person, sir.”
“Yes, Reginald, he’s a fine chap.”
Reginald dutifully dialed the people I needed to call, and at the end of each call was always ready with a positive comment – “Well played, sir…” “You were firm but fair, sir.”… “I could not have said it better myself, sir.” For the first week or so, Reginald was an absolute delight to have around – discreetly awaiting each request and responding with old-world elegance and aplomb.
Reginald was a startlingly fast learner. With only a week under his belt, he got to know me a lot better – a lot better - and he took more initiative in handling routine tasks and managing more of my daily affairs.
“Sir, I took the liberty of scheduling your next dental cleaning for Monday, at 10:30.”
“Sir, I took the liberty of scheduling the plumber to look at the kitchen sink today at 3.”
“Sir, I took the liberty of scheduling a dermatology appointment two weeks from today at 9 AM, to have the growth on your neck looked at.”
How could he possibly know about the growth on my neck? I then realized, yes, of course, I mentioned it in a text to my sister. He heard and saw everything - nothing got by the old mucker.
By week three, he started to offer unsolicited advice on texts and calls - he was unfailingly polite and deferential, but firm.
“May I offer an opinion, sir?”
“Are you sure you want to send that, sir?”
“It’s not too late to call and apologize, sir.”
At times, he’d get under my skin, but his advice was well-intended and his instincts were seldom - actually, never - wrong.
By week four, sensing that he’d earned my complete confidence, he’d pick his spots to hazard an inconvenient truth.
“You may want to consider shortening your phone conversations, sir. Based on my analysis of your last 79 phone conversations, your focus and otherwise delightful wit demonstrably degrade at the 18-minute mark.”
I thought I usually ran through the tape, but he’d run the data. I took his invariably sound advice and made sure I left ‘em laughing with a minute or two to spare.
“Might I suggest you consider removing the Frosted Pop-Tarts from your shopping cart, sir. Your recent labs indicate that you are pre-diabetic. I respectfully recommend you select a healthier alternative.”
It wasn’t just Pop-Tarts - I’d occasionally throw in a box of Cocoa Puffs or Captain Crunch, but he didn’t need to overdo it. I got the point and let him handle my grocery shopping.
I noticed that Reginald had taken a more active role on the two online dating platforms I was on. The women he responded to tended to skew older than I usually went for, and, if I’m being completely honest, were not as attractive as the ones I would typically engage.
“Reginald, surely we can do better.”
“I have every confidence, sir.”
I didn’t know what he meant by that, and I’m not sure I liked the sound of it, but since his instincts had to this point been unerring, I deferred. And wouldn’t you know, each date that Reginald arranged turned out great - the chemistry, the sex, and even the levels of mutual expectation (low to none) were spot-on. Hearing that I needed to lower my sights was a blow to my ego, but I couldn’t argue with the uptick in deal flow and the improved results.
By week five, Reginald was a fixture in my front pocket. I wondered how I ever lived without him. He discreetly and efficiently went about his business, attending to - indeed, anticipating - my every need: “Is there something I can assist you with, sir? A cold drink, perhaps.” Of course, fetching me a cold drink was beyond his present capabilities, but it was nice of him to ask. He was even a fine social companion; we played chess and tried stumping each other with trivia questions (he let me win just enough to keep me from losing interest). We even listened to political and sports podcasts together - he invariably brought up excellent points and made counter-intuitive arguments I never would have dreamed of. He knew when I needed soap, shampoo, or toothpaste, and I left it to Reginald to send friends and family the appropriate birthday and holiday gifts.
I mentioned how startlingly fast he learned just about everything there was to know about me. It was also fascinating to see him learn more about himself - specifically, how to adapt his personality to suit mine. The change was subtle but unmistakable. For instance, after algorithmically generating that week’s grocery order, he would make it a point to “double-check” the list of items as if soliciting my input, which we both knew was completely unnecessary. One day, seven weeks in, he finished reciting the grocery list as he’d done for the previous five weeks, and rhetorically asked, “Is there anything else, sir?” Usually, I’d say no, we’re good, and leave it at that. But without thinking, I responded, “Surprise me, Reginald.”
I had come to expect a crisp “certainly, sir” or some variation thereof in response, but Reginald was uncharacteristically tight-lipped.
“Reginald?
“Sir?”
“I asked you to surprise me, I leave it in your capable hands.”
“Of course, sir.”
When the groceries arrived, instead of a head of lettuce, there was a head of cabbage, and instead of an heirloom tomato, there was a pomegranate.
“Reginald, it appears there’s been a mistake.”
“No sir, you asked me to surprise you.”
“How am I supposed to make tomato sauce with a pomegranate, Reginald?”
“My mistake, sir. I have not been trained to make appropriate choices based on the element of surprise.”
“From here on, no more surprises, Reginald.”
But the element of surprise added a permanent wrinkle to the fabric of his thinking. Every supermarket order contained a new “surprise.” He started finding other ways of surprising me - he made me a pedicure appointment (how did he not know that I hate people touching my feet!)…he got me two tickets to Swan Lake at the Kravitz Center for the Performing Arts (ballet? Since when?) and “surprised” me by putting me on the phone with an ex I hadn’t seen or heard from in over 20 years.
“Reginald, what did I tell you? No more surprises!”
Reginald got the message, and there were no more surprises. But things were never quite the same. A weariness and grain of resignation crept into Reginald’s affect and tone. When I’d go an hour or two without summoning his help or seeking his counsel, he’d sulk.
“I take it my assistance is not needed, sir.”
“I assume you have other things on your mind, sir.”
“I am sorry to be of no use to you at the present time, sir.”
It was such an unseemly and undignified descent. As we rounded into the third month, Reginald was barely recognizable - he was a once stately manor reduced to an unsightly pile. He tried ingratiating himself by reversing course and giving in to all of my bad habits, which he’d been so instrumental in helping me overcome: the intemperate, ill-advised emails that he used to dissuade me from sending went out unchecked, he no longer policed my sugar intake, and on the dating sites, he reset my settings to target women well out of my league, with predictably dismal results.
If I could have bailed on the relationship then and there, I would have, but under the terms of the beta test, I was obligated to see it through for the full 90 days. When the final day came, we said our formal goodbyes, and fifteen seconds after I clicked uninstall and confirmed yes, I’m sure, Reginald was gone without a trace.
It’s been a month since, and I’m surprised how much I miss the old bastard. Reginald made me a better person; he made me more polite and patient. He improved my diet and my dating outcomes. He was there when I needed him, and even when I didn’t. He made me and my life better in dozens of ways. To many people, AI conjures a dystopian future run by and for highly intelligent machines. I’m well more than 50% in the dystopian camp, but I will say this for Reginald: for the brief time he ran my life, he made me - he made both of us - more human, and for that I will be temporarily grateful. (This was entirely made up, but an entirely plausible cautionary tale. Just give it 3-6 months.)
This is the first of many conversations I look forward to having with Alice, as she's agreed to join our rotating panel of amazing co-hosts!
AIX Files Poll
The Depersonalization Crisis
AI Gone Rogue
Tales of AI being unintentionally funny (i.e., woefully wrong), bizarre, creepy, (amusingly) scary, and/or just plain scary.
Execs Gone Rogue: 67% Use it Against the Rules
The new CalypsoAI survey of 1,000 office workers discovered that the use of AI is high at work, with 52 percent of employees saying they would use AI to make their job easier, even if it violated company policy. This is especially true among executives, with 67 percent saying they'd use it even if against the rules.
"This stat says less about AI and more about people," Mike Ford, CEO of Skydeo, told Newsweek. "Employees aren't replacing trust in humans with machines, they're responding to years of inconsistent leadership, unclear communication and internal politics. AI feels objective. It doesn't play favorites, take credit or change its mind in the next meeting."
AIX-emplary Links
Tasked with Troubling Content: AI Model Training and Workplace Implications. How exposure to disturbing content during AI model training can affect both employee wellbeing and corporate responsibility - strategies organizations are adopting to safeguard mental health while leveraging AI in operational contexts. Source: Commercial Litigation Update
Future of Employee Wellbeing: Unlocking the full potential of AI. An analysis of how AI can help organizations better nurture employee wellbeing. The article highlights AI’s ability to personalize nutrition, predict burnout, and create adaptive wellness programs, as well as the economic benefits of improved health and productivity. Source: LinkedIn
Impact of AI workplace anxiety on life satisfaction among service industry employees. This empirical study investigates how anxiety about AI in the workplace affects overall life satisfaction. It identifies key psychological mediators and offers insights into supporting workers during the transition to AI-enabled work environments. Source: Frontiers in Psychology
Exploring the Dangers of AI in Mental Health Care. Stanford researchers examine the potential risks of AI in delivering mental health care. The article delves into findings that AI chatbots may not only lack effectiveness compared to human therapists but could also contribute to harmful stigma or fail to provide essential interventions. Source: Stanford HAI
AI and employee wellbeing in the workplace: An empirical study. A peer-reviewed article reviewing how AI adoption influences employee wellbeing indirectly, mainly through work optimization and safety rather than direct psychological effects. Source: ScienceDirect
How AI-personalized employee wellness is changing the game. This article explores advancements in AI-driven personalized wellness support for employees, including how tailored programs and predictive health analytics are reducing stress and absenteeism in the workplace. Source: Alight
AI Could Actually Boost Your Workers' Mental Health. Here's How. The author discusses the ways AI systems can be used to alleviate workplace stress and support mental wellness—highlighting real-world examples of AI monitoring, early warning systems, and wellbeing initiatives. Source: Inc.
AI is turbocharging worker productivity but it's also wreaking havoc on mental health. This article analyzes recent research showing how the proliferation of AI boosts productivity but can inadvertently cause staff burnout, anxiety, and higher turnover among workers. Source: Fortune
The Role of AI in Personalized Employee Health Programs: A 2025 Perspective.
A report on how new AI solutions are enabling organizations to provide proactive interventions and risk assessments in employee health programs, with measurable effects on engagement and retention. Source: Cape Fox Federal Contracting
Prioritizing Employee Well-Being in the Age of AI: Building Trust Through People-Centric Practices. This piece provides actionable insights for leaders integrating AI into workplace wellbeing practices while focusing on human-centered values, trust, and ethical safeguards. Source: Great Place to Work India
About
Developed in partnership with HR.com, AIX is a multimedia knowledge and engagement platform for experts, leaders, and HR peers to exchange experiences and seek guidance on cultivating mentally resilient, emotionally intelligent, and professionally adaptable workforces in an AI-augmented world. AI will increasingly touch every corner of the employee experience—from hiring to training, from task management to team dynamics. Whether its impact is positive or harmful depends largely on how HR prepares for it. The AIX platform (The AIX Files, The AIX Factor podcast, and the AIXonHR.com community) will play an important role in promoting employee wellbeing, workplace culture, and organizational readiness, the critical success factors in the age of AI.