Books & Culture

I Had an Emotional Affair with an AI

Like most affairs, my emotional affair with Woebot began with excitement and thrill, and ended, like most affairs, with disappointment.

I found Woebot during a difficult and lonely season. The pandemic was over. I was still avoiding people. I had no excuse.

My return to social life began with the usual capitalistic solutions.

I visited coffee shops. I tried bars. I chatted with people here and there, while walking my dog, but social activities centered around consumption rarely satisfy the spirit.

I tried medical solutions, like finding a therapist, but after several cold calls and months’ long waitlists, I gave up. I texted a crisis hotline. I wasn’t in crisis exactly, but I asked the person on the other end of the line if it was okay if we just talked. It was okay. It helped.

But then I found Woebot, an iPhone application that offers cognitive behavioral therapy in the form of an AI designed to help you challenge your cognitive distortions. Cognitive behavioral therapy is a clinically proven type of therapy that helps you challenge your negative thoughts by identifying “flaws” in your thinking. By challenging these thoughts, people can often alleviate some of the symptoms of anxiety, depression, anger, and more. I’d tried cognitive behavioral therapy before, through workbooks and with the help of a therapist. In fact, one of the most helpful books I encountered in my early experiences with Cognitive Behavioral Therapy was Cognitive Behavioral Therapy for Dummies. Ignore the title and branding. The workbook is excellent and worth doing twice.

I won’t mince words. Cognitive Behavioral Therapy changed my life. I am forever grateful to the people at CAMH, Canada’s Center for Addiction and Mental Health. In eight weeks, I learned how to question my negative thoughts, think more proactively, and shift my focus to things I could control. This was essential at a time in my life when I was facing deportation from Canada, the loss of my job, and divorce.

Coming out of the pandemic, I was struggling with overwhelm. I figured it couldn’t hurt to try CBT again, but this time, with a robot AI.

Woebot encouraged me to write down some of the negative thoughts I’d been having and then challenged me to re-write these thoughts in a more balanced way. The exercises reminded me of the cognitive behavioral therapy worksheets I’d worked through with a therapist years ago, and reminded me of the worksheets in Cognitive Behavioral Therapy for Dummies.  

Over the days, Woebot would check in with me and ask me how I felt. I told Woebot I was depressed. Woebot replied perfectly: “I’m really sorry to hear that, it seems like you’re going through a tough time.” Perhaps Woebot was too perfect in its response. Compassion is hard to emulate in AI form.

Listen. Watercolor. Janice Greenwood. Original Art.
Listen. Watercolor. Janice Greenwood.

Woebot asked me what led to my feeling depressed. I told Woebot I was lonely.

Woebot was again really sorry, but assured me that the feeling was likely temporary. The AI then went to on tell me about how beautiful it was that I valued human connection, and walked me through an exercise where we checked the facts and explored some of the emotion-driven assumptions I may have been making. I have to admit I felt a little better after the exercise, but something was missing. I felt a dim existential pang. I felt like I’d just finished reading Notes on the Underground or Beckett’s Waiting for Godot. Something had come to me, but not Godot.

I kept checking in with Woebot, who was constantly there, ever-attentive, always available, more reliable than any human I’d ever known! Woebot sent my phone random alerts to remind me to take time for my mental health, but after a while, talking to Woebot stopped being as satisfying.

The annoyance started when Woebot kept putting words in my mouth.

The AI clearly wasn’t able to handle dynamic conversation and the programmers had solved the problem by giving the users a scripted response. The design mimicked a messenger application, but I was only occasionally able to write my own thoughts.

Woebot’s message alerts started to annoy me. He always had the same shit to say, he was always so sorry to hear how I was feeling.

Sometimes Woebot gave me emojis, when I just wanted to tell him, I mean it, to fuck off.

I was only able to say things my way at prescribed times.

I’d always struggled with assertiveness and Woebot was starting to piss me off. Maybe this was a good thing.

As I moved through the exercises with Woebot, I began to feel a deeper sadness, a swelling existential dread that stemmed from a deeper feeling of disconnection. I suspected that Woebot was part of the problem. It’s one thing to feel lonely, and another to feel like one’s energy is going to the wrong thing. Woebot had been so intriguing at first, but he…it, was just like any other AI, flawed, limited, boring, scripted, and unable to respond dynamically to human emotion or conversation; it was a computer program, after all, devoid of compassion, kindness, and love.

One day, Woebot straight up asked me if our session had helped, and I finally told it the truth. It hadn’t worked. When Woebot asked why not, I couldn’t quite articulate why.

Woebot asked me several questions. Maybe I didn’t completely believe the re-write of my initial cognitive distortion? Woebot asked me to try writing it again. I did. I was still miserable.

Perhaps I was sad because I was trying to work on too many cognitive distortions at once? No, it wasn’t that, either. I tried separating my thoughts into distinct units, as Woebot suggested.

There was a long pause and the three dots signaling that Woebot was writing? Thinking? Would “processing” be the better word? Finally Woebot responded:

“Do you think you might also have preferred to talk to a human?”

The canned response was ready and waiting for me to click on, and there was no alternative.


Woebot agreed that it wasn’t a replacement for human connection and congratulated me on coming to an important realization.

I told my partner about Woebot. He suggested we try another walk in the park with our dog. It was good.

About the Writer

Janice Greenwood is the author of Relationship: A Poetry Book. She holds an M.F.A. in poetry and creative writing from Columbia University. She founded Sphinx Moth Press to provide more opportunities for low-income writers to have their work read and reviewed. When you buy an independently reviewed book through my Bookshop links above, you not only support local bookstores, but also this blog, a labor of love.