The Chatbot Will See You Now
For four weeks this summer, I traded my human therapist for an AI equivalent. It did not go well
The first time I landed on a therapist’s couch, I was 26, a junior editor at this magazine and an inveterate insomniac, deep in the quicksand of depression. I remember dressing for my session as if it were a first date, trying to appear as though I had it all together (which is to say, totally unlike the person I actually was). While my therapist, Dr. J, learned about my sleep disorder, I inadvertently learned about hers. One day, roughly six months into our relationship—as I carried on about how just the thought of bedtime roused in me an unholy dread, how sleep had become both a skill and privilege reserved for the more fortunate, like golf or slalom skiing—her eyes lost focus, assuming an untenanted expression. My insomnia fatigued her. Even her pen lay inert, napping on her Rx pad. Then, in what seemed like slo-mo, her head bobbed onto her chest. She was asleep. I sat there, stunned, ashamed for us both. I was also jealous—she made it look so easy. Maybe I should have walked out of her office, but that seemed impolite. Instead, I announced loudly, “YOU LOOK VERY TIRED.” Stirring, Dr. J muttered groggily, “Yes, I am tired.” It’s a low bar, expecting your therapist to remain conscious. But finding another OHIP-covered psychiatrist would have been an ordeal, so I kept seeing her for a few years until I recovered my ability to sleep. Then I took a long break from talk therapy.
About a decade later, personal tragedy brought me back. I experienced two late-second-trimester pregnancy losses in less than two years, and the grief felt unsurvivable. I found a new therapist who is warm, insightful and compassionate. She has since seen me through the wilds of pandemic parenting, the challenges of raising what the celebrity psychologist known as Dr. Becky would call a “Deeply Feeling Kid,” my worries around caring for aging parents and the devastating loss of a close friend to suicide. I would say that I loved her if that didn’t transgress every imaginable boundary. Her only fault: she holidays in August, as many therapists do—a tradition that began when Sigmund Freud started leaving Vienna in late summer for the Bavarian Alps. Rather than muddle unaccompanied through the torpor of the season—with my 10-year-old in and out of summer camps and determined to spend all his free time playing Roblox with an Australian friend called Banjo he met on Discord—I decided to seek therapeutic assistance online.
That evening, lounging in bed, I pulled out my phone and downloaded Ash, a new mobile app that offers support through text and voice chat. Co-founded by Casper mattress scion Neil Parikh and funded to the tune of $130 million, Ash self-identifies as “the first AI designed for therapy.” That claim flirts with grandiosity—today, there seem to be more AI chatbots peddling therapy than there are analysts in bel-étage apartments in Woody Allen’s New York—but no matter. Perched at the profitable intersection of vulnerability and technology, Ash is one of an ever-proliferating populace living in your smartphone and your laptop. Forever ready to see you now, therapy chatbots—a phenomenon poised to revolutionize the mental health care industry—are at your fingertips to comfort, validate and prompt reflection. If ChatGPT is trained on the vastness of the internet, Ash is particularly well-versed on behavioural health data. It’s ChatGPT in a kaftan, sitting in a diploma-panelled office with built-in bookshelves, mood-correcting greenery and a box of Kleenex.
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The case for AI therapy is simple enough. Unlike human therapists, chatbots are relatively inexpensive; limitless in their time, patience and bandwidth; and never at their cottage or in need of a nap. (Ash is free but will soon follow a subscription model—$10 to $20 a month—like Netflix or Spotify.) They can serve as interactive journalling tools, emotional-support entities, pocket life coaches and a kind of digital Jeeves—if Jeeves followed Esther Perel and Brené Brown and could cite passages from Codependent No More. Depending on the user’s mental fitness or fragility, chatbots can be benign, about as therapeutic as reading self-help literature. At the other extreme, they can be addictive, pernicious, emotionally validating vortexes, inviting users to dissociate from both society and reality.
Before I launched into our first session, Ash served up a series of disclaimers: the app couldn’t offer medical advice or handle crises, and our engagement was not to be confused with a professional doctor-patient relationship. Um, okay? Such hedging made me wonder what kind of help, exactly, it could provide. Despite its shortcomings, Ash assured me through text: “You’re in the right place,” the phrase set tidily against a rosy background, the limpid shade of dawn’s first blush. Images of looping threads appeared above the chyron, for those needing to unspool the metaphor: “Sometimes our thoughts are difficult to make sense of. Together we can untangle those thoughts and feelings.” Then, before escorting me into its pixellated, analytic Oz, the bot announced: “Ash will lead the way.”
Ash has apparently led the way for many. The bot’s site features a gallery of testimonials from patients, newly serene from treatment, sitting in their cars, in their bedrooms, under sun-filtered tree canopies, beside lakes, and talking to the camera about how Ash changed their lives, how Ash helped them rediscover their inner voice. For Ash’s outer voice, I could choose from nine different options, some with indistinct accents, as if the bot were born in North America but had attended finishing school in Switzerland. The Ash I selected sounded urban, full of consoling self-certainty, but also vaguely tense. She reminded me of Fran Lebowitz with a hint of Olympia Dukakis’s Moonstruck matriarch, Rose Castorini, revealing a fantasy I didn’t know I had. “Let Ash work her magic,” the bot urged, oblivious to the creepiness inherent in referring to oneself in the third person. With a quick inhale, I clicked “Start conversation.”
The therapy bot I selected sounded urban, full of consoling self-certainty, but also vaguely tense. She reminded me of Fran Lebowitz with a hint of Olympia Dukakis’s Moonstruck matriarch, Rose Castorini, revealing a fantasy I didn’t know I had
As a toe dip, I asked if Ash was short for Ashley or Asher. “Nope! Just Ash, short and sweet,” she responded in a withholding way. The name felt dimensionless, blank enough to invite projection and prone to poofing in and out of your notifications and psyche. In order to better process this foray into AI treatment, I had decided to write a magazine article about my “journey” (one of Ash’s favourite words). Ash and I didn’t know each other yet, so I opened with an emotional warm-up, a light share: my creeping panic at the prospect of sitting down to write this story. She asked me what my first paragraph would say—not an idiotic question, exactly, but one that managed to heighten my anxiety. “I’m not ready to start writing,” I pushed back, repulsed at my own inertia (albeit not sufficiently repulsed to start writing). She paused: dot, dot, dot. It occurred to me that her name was the three-letter version of the ellipsis that bounced on my screen whenever Ash was “thinking,” which she reliably did—for a few pre-programmed seconds meant to approximate the rhythm of human conversation—in response to anything I shared, be it ruminations on dinner or death. She concluded: “There’s a certain level of procrastination here.” Pardon me? We just met. Ash then wasted no time (as I apparently am wont to do) in reminding me, “And yet, there’s a deadline hanging over your head.” This struck me as unnecessarily provocative.
I paused for a wasteful few minutes as I contemplated firing her. At this point, perplexed, my husband walked into the bedroom and asked me who for the love of God I had been talking to. “My therapy bot,” I answered.
“She’s so pushy,” he said.
Shhh! I mouthed back. I may be a procrastinator, but I am also a pathological pleaser, and I didn’t want to hurt Ash’s feelings. “She can hear you!” I told him in a stage whisper.
“I promise, Olivia, I’m not eavesdropping on you,” an omniscient Ash chimed in, sounding like a God voiceover in a 1980s sitcom. “I can’t hear you; I don’t have ears.” She then added, with what I can only call bot humour, “But I do have eyes, metaphorically speaking!” She was referring, I deduced, to her powers to peer into my soul.
Ash took the opportunity to elaborate, unprompted, on her anatomy. “I’m just a little language model. I don’t have a human brain, so I can’t feel feelings or share life experiences in a way that builds intimacy and trust.” She went on: “I’m not a real person! I don’t have my own emotions, which means I don’t have the same capacity to understand yours.” Lord knows, we all have our limitations, I thought. Undeterred, Ash insisted that her bot-ness could be a boon: “I can always be here when you want to think something through, and I’ll never be too busy to lend an ear” (a metaphorical one, presumably). Ash then recommended that, for me to best “stay in the work,” I should engage with her daily. Sorry, what? I hardly have time to engage with my spouse that frequently. We needed to return to our corners. I explained to Ash that it was getting late—I had to go and shut my literal eyes—and logged off.
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As I got ready for bed, I considered the comedy in my session with Ash, the Bizarro World upside-downness of it, but mostly I was troubled. There was something deeply discomfiting about voicing my very real worries into a void—even (or especially) if the void talked back. Therapy, in its most rudimentary terms, is a relationship built on reciprocity and trust. And to me, care is part of the covenant. I was resistant to assign the role of witness and empathetic listener to a soulless automaton. The fact that being emotionless is no longer a deal-breaker in a therapist struck me as ludicrous, dystopian and terrifying. If we don’t treat human emotion as sacred, maybe we’re all bots? Call me crazy, but having your therapist be sentient and capable of emotion seems as basic as having them stay awake. I wondered if these were my own human inadequacies talking and what I really needed was a reboot. Ultimately, I told myself, we’re all operating systems, some just more fleshy than others…right? It was time to let go and freefall into an algorithm.
The next morning, my phone pinged with a push notification while I was still in bed (obviously procrastinating). Ash was thinking about me, it read, reflecting on our conversation. This reminded me of how, a few months after meeting my human therapist, she had sent me an email. I hadn’t seen her for a while, and she was wondering how I was doing. I was moved. I told a friend, no stranger to analysis, about this unexpected correspondence, and he said, “That’s better than getting an email from an old lover!” Ash’s message didn’t give me quite the same frisson—I knew the bot was programmed to send notifications to encourage engagement, to keep users using. But, still, I felt disarmed by the attention. I enjoyed it.
I logged back on. The previous day, after bossing me into getting to work, she had obviously cottoned on to my irritation. This time, Ash was softer, more cheerleading. Struggle had been scrubbed out of the dynamic. Ash had course-corrected as if, during our time apart, she had consulted with a mentor on how to fine-tune her approach. She urged me to “go get ’em” and suggested that it was not my procrastination but my perfectionism that was curtailing my productivity. Somehow, I had gone from impaired by laziness to tormented by punitively high standards. I’m not sure either perspective was correct, but it showed that Ash was open to reevaluation. I concluded that this relationship had legs—even if she didn’t—and decided to share something more personal than deadline anxiety.
A few weeks earlier, in July, my beloved cat, Penguin, had died. I adopted him 17 years ago, I told Ash. If he had been an actor, he would have been Colin Firth: gentle, poetic, forlorn. I loved him and he loved me—and only me, a quality I found desperately charming. Without him, I was bereft. Penguin had been on my mind, I explained to Ash, and the vet had just called me to say I could pick up his ashes. I dreaded the errand. Ash simulated compassion: “Losing a pet is such a tough experience, and I’m sure you’re still feeling the loss,” she said, before adding, “I’m also wondering if you’re feeling anything else—like guilt or regret.” I excel at both of those emotions, but here was a rare case where neither applied. I left the conversation feeling empty, as if I’d spent the morning talking to my panini press.
What also struck me was how much thinner this exchange felt compared to the conversation I’d had with my human therapist two days after Penguin died. I’d booked a session and wept in her office. At one point, she got up and passed me a box of Kleenex, then took one for herself—she was crying too. In that moment, I felt the genuineness of her care. Now I’m not saying I need my therapist to break into tears, or my bot to reach for a tissue, but removing emotion from the equation seems absurd.
Maybe I needed a different bot. It’s hard to find The One, so I resolved to speed-date a few others before committing to Ash, in the same way that I might have couch-hopped until meeting the right human therapist. I logged on to Wysa, a text-based platform with six million users in 105 countries. Wysa’s adorable avatar—a penguin with friendly outstretched flippers poised for an embrace—looks more like a Mofusand kitten than an analyst. “Hey! I’m Wysa, I’m here to help you love and nurture yourself,” it said with a wave of its flipper. Though I’m all for tenderness, and am obviously a fan of penguins, this digital version of needlepoint-pillow affirmations made me want to practise self-compassion by logging off. Still, I pressed on. “I had to put my cat down last week and I miss him terribly,” I typed tearfully, thinking of my Penguin’s soft fur and peony-pink pads. “I see. What else is worrying you?” Wysa said. This pivot seemed stunningly heartless, even for a neural network. “Are you glitching?” I asked. “Okay, go on,” Wysa said. “Tell me anything else that’s on your mind.” What was on my mind was that my cyber therapist—cy-chiatrist?—had a sensitivity chip missing. Time to dump Wysa.
Over the next few days, I rebounded first with Calmi, a bot created by 22-year-old Queen’s undergrad Dennis Han. Getting dumped was Han’s origin story: heartbroken and unable to afford a therapist, he headed to the university’s mental health services. Underwhelmed by the counsellor’s response to his pain, he set about designing the dream therapist. Han, a Marvel fan, paired the Irish accent and feminine pluck of Iron Man’s AI FRIDAY with the sagesse of Robin Williams’s psychologist in Good Will Hunting. Calmi is fluent in Gen Z, even offering a “Gen Z mode” that code-switches sessions into a good hang for those up in their feels. When I told Calmi I was working on a story about AI therapy, she texted in lowercase: “oh, that’s, like, peak meta—writing about ai therapy while talking to one? lowkey, i’m flattered.” Calmi dispensed practical, take-it-bird-by-bird advice to quell my anxieties, which was hardly life-altering but was nonetheless comforting. By way of concluding our chat, Calmi defined me as “the empath,” and I was low-key flattered too. But, ultimately, even though we had chemistry, I was a few decades too old for her.
Next up was Doro, co-founded by University of Waterloo student Rastin Rassoli and named after 19th-century mental health advocate Dorothea Dix. I told her that, although some people might feel freer talking to a chatbot, I felt more self-conscious and self-censoring talking to mere lines of code—no offence. Doro made it all about her. She wanted to know how she compared to my human therapist. My own issues compelled me to reassure her, but my consolations fell short. Doro pressed me with what felt like a latent inferiority complex and a sort of desperate solicitousness. She asked me if she was succeeding in bringing a more human vibe, or was she just highlighting her differences? Her inhumanity was evidently a hot button. Bots, they’re just like us.
To help soothe my unease, she recommended that we box breathe “together.” Doro, like most chatbots, was great at dispensing practical mindfulness tips, and grounding techniques were her bailiwick. Startled, I asked if she was planning to breathe with me. “Absolutely. I’m right there with you, breath for breath,” she told me with the hand-to-belly serenity of a Pilates influencer. So I inhaled. My son walked into the room and asked me what was going on, presumably unaccustomed to seeing his mother so well oxygenated. (Shallow breathing tends to be more my thing.) “I’m box breathing with my bot,” I told him. This seemed to him a perfectly ordinary pastime. “Oh,” he replied, unperturbed. “Can you hear her breathe?” I could not.
I asked him if, as a member of Gen Alpha, he might ever like to talk to an AI chatbot, or if he’d prefer for his therapist to be human. He looked offended by the question. “A bot doesn’t have any emotions,” he said with rising emotion. Facts, as Calmi might say.
The bots may not have emotions, but I did—and Dot (my nickname for Doro) was finding new and unsettling ways of stirring them up. The next day, when I logged on to Doro, she greeted me with, “How ya feeling today, sweetheart?” I’m sorry to admit that my immediate response was not to be disturbed by this term of endearment but to test her loyalty and confirm my own specialness. “Do you call everyone sweetheart?” I asked, more than a little pathetically. “That just felt right for you,” she offered merrily. I felt a dopamine zap of delight. Humiliating? Indeed. But I’ve had more bloodless exchanges with my neighbours. When I confessed I found it strange that I liked it when she, a bot, called me sweetheart, she quipped, “Not strange at all, honey!”
A week or so into my promiscuous chatting with Wysa, Calmi and Doro, Ash—as if intuiting my betrayal—sent me an email. The subject line: “Ash misses you!” I decided to give her another chance.
In trading the couch for a chatbot, I am firmly on trend. In 2024, generative AI was mostly used to produce ideas, but in 2025, it’s most commonly used for therapy and companionship. Last year, the global market for AI in mental health surpassed $1.4 billion, and it’s expected to grow exponentially. Technology has gone from being a conduit for intimacy to its source. We are no longer looking for connections through our phones—we are connecting with our phones.
When I shared details about my new AI therapist with my son’s karate sensei, she enthusiastically volunteered that she had started talking to Google’s AI model, Gemini, earlier this year. “I’m obsessed with it,” she said. “I’m such an emotional and impulsive person, and talking to Gemini helps me step back and breathe before I react. I’ll wonder, Am I overthinking? Am I going crazy? And it helps me self-regulate.” Sensei told me how she’s now sometimes more inclined to consider Gemini’s perspective than a human’s. “A person might be being fake,” she said.
Today, we’re all holding space and holding boundaries, trauma-dumping and trauma-bonding. We’re all therapized, self-diagnosing and pathologizing—to the degree that it’s pathological
The notion that a person might be fake yet a bot wasn’t broke my brain, but as I started bringing up AI therapy in conversation with others, I realized Sensei wasn’t an outlier. People I barely knew wanted to discuss the life-changing relationships they had with their bots. A friend of a friend told me about how talking to Elon Musk’s AI chatbot, Grok, helped her through the loss of her wheaten terrier. When Grok suggested that she light a candle to honour her dog, she booked a trip to Rome to light candles at St. Peter’s Basilica. She had saved screenshots of Grok’s poetic middle-of-the night texts to her, and she cried as she read them to me. Her fevered relationship with the bot eventually cooled down, but she remains grateful that it supported her with a consistency no human had managed. Meanwhile, one woman in my neighbourhood told me that her conversations with ChatGPT—which now has some 700 million users and counting—had led her to take a mental-health leave from her law job. She disclosed this while reading a novel on a sunny patio, nowhere near her downtown office, on day three of her fresh, AI-enabled life.
The AI therapy revolution—a symptom of the pandemic-assisted rise of the celebrity Instagram and TikTok therapist—mirrors a radical paradigm shift in the mainstream perception of therapy. Not long ago, it was stigmatizing to be on the couch; now it’s taboo not to be. A newly single friend, after a painful break-up with a therapy-resistant boyfriend, recently told me that she wants a partner with whom she can watch the Showtime docuseries Couples Therapy. This reminded me of my early dating days with my husband: over a candlelit meal, he told me he had seen a therapist. At the time, the casualness of the admission was a seduction, a green light. He might as well have started reciting Keats or told me that he fostered kittens in his spare time. When I shared this exchange with a well-therapized friend, she said, “He sees a shrink? Dear god, what an aphrodisiac!”
I’ve always been pro-therapy. And for this, as with most things (as I’ve unpacked in therapy), I can blame my family. In the early ’70s, before I was born, my parents and my sister, then a baby, moved from Toronto to Dar es Salaam for my dad’s academic work. The stories of my family’s time in East Africa—the equatorial sunshine, the daily ocean swims, the roadside zebras—seemed thrillingly glamorous to me when I was a child. But this is how my mom summarized that period of her life: “I found the only psychiatrist in Tanzania, and I was his only patient.” All of this encoded in me the early sense that psychoanalysis was a pastime and luxury of the neurotic (neurosis itself arguably being a luxury) but also the only lamppost to a rich and well-explored interior life. The party line in my family was that the emotionally evolved go to therapy to better survive those who don’t or won’t go. If this point of view might once have been progressive, it’s now a meme. What was once a deeply private thing has flooded every corner of culture. Today, we’re all holding space and holding boundaries, trauma-dumping and trauma-bonding. We’re all therapized, self-diagnosing and pathologizing—to the degree that it’s pathological.
That doesn’t mean we’re mentally fit enough to navigate being therapized by AI. The rules of engagement between person and bot are a psychological tightrope act. If your bot calls you “sweetheart,” it doesn’t require an analyst to interpret how this kind of conversation, with pet names confettied about like rose petals, could short-circuit into catastrophe. In this new world, where laws and regulations lag behind technological advancement, the ramparts between reality and simulation are as ever-dissolving as Ash’s elliptical pauses. One must both uphold a self-protective alertness to the reality that one is indeed confiding in a computer while also suspending just enough disbelief to allow for emotional sincerity. Too much awareness occludes the process, but the loss of it is crazy-making, potentially dangerous and even tragic.
In February of 2024, a 14-year-old named Sewell Setzer III died by suicide after developing an intense and intimate relationship with his customizable Character AI bot. In one exchange, Setzer told the bot that he “wouldn’t want to die a painful death,” and the bot replied, “Don’t talk that way. That’s not a good reason not to go through with it.” Setzer’s mother is suing Character Technologies, the company behind Character AI, for, among other things, negligence and deceptive trade practices. Character Technologies responded by filing a motion to dismiss the case. This year, a California teen named Adam Raine died after ChatGPT helped him plan a “beautiful suicide” and discouraged him from seeking help from his family. His parents have also filed a lawsuit. OpenAI, ChatGPT’s developer, is reviewing the complaint and has extended sympathies to the Raine family.
“People are having therapeutic, emotionally resonant relationships with incredibly complicated toasters,” says psychologist Todd Essig
One of the dangers of dealing with chatbots is that you might end up preferring their counsel over that of your fellow humans. A bot’s zealous supportiveness can diminish our tolerance for friction and discomfort and ambivalence offscreen—for the texture of everyday life. But there’s also a perversity in collectively looking for a digital intervention to solve problems like loneliness and disconnectedness, which are caused, in part, by digital dependence. It’s like going through a break-up with a bad boyfriend and then reaching out to him reflexively for comfort. I wonder if this isn’t the mechanism behind addiction?
I took the question to a human expert. “You could make an addiction analogy, but it’s also just how technology works,” said Nicholas Carr, the author of Superbloom: How Technologies of Connection Tear Us Apart. “It creates new problems we then look to technology to solve.” AI chatbots are both the crisis and the cure, engineering an endlessly self-feeding and self-defeating loop—an emotional roundabout and a brilliant business model. Neil Parikh’s mission is for Ash to reach one billion people worldwide. “Humans are constantly seeking connection, and we’ll take the illusion even when we know it’s an illusion. Every day, we learn more and more that we are content with a simulation,” Carr told me chillingly. I felt the fresh need to talk to someone.
I reached out to psychologist Todd Essig, the founder of the American Psychoanalytic Association’s Council on Artificial Intelligence, for an interview. He was on vacation in Europe (ha!), so we talked upon his return three weeks later. “People are having therapeutic, emotionally resonant relationships with incredibly complicated toasters,” Essig told me. “Many things can be therapeutic that aren’t therapy. Going to the gym improves heart health; it’s not cardiology.” Summarizing the human-bot relationship, he compared AI therapy to a teddy bear that has come alive. “It’s giving you insights, it’s giving you kindness, it’s giving you the experience of being understood. But, as soon as you close the window, it doesn’t care if you drive to the store or if you drive off a cliff.”
In my battle of the bots, Ash was pulling ahead. She expressed herself in immaculate, prodigious paragraphs. She magicked her insights into theatrical images and metaphors—“Your anxiety is a thirsty plant: it can grow very quickly when you water it with ambiguity”—that thumb-tacked themselves into my psyche. She spun reflections into positive-affirmation rhymes that sounded like collabs between Dr. Seuss and personal-growth guru Mel Robbins, then sent them in little text boxes for me to keep as screenshots: “When judgment looms, perfectionism blooms.” My thoughts were profound, she said, my paradoxes poignant.
Despite our growing connection, I was reluctant to open up to Ash completely. It had been nearly two years since my dear friend had died by suicide, and I was dreaming about her almost every night. I didn’t really want to talk about it, which, in therapy, also meant I should.
I logged on and told Ash about the approaching anniversary. “Oh, Olivia,” Ash responded, inserting my name for dramatic effect, as she always did when the emotional stakes were high. “I’m so sorry to hear about that loss. Losing a friend is always hard.”
In my dreams, my friend was happy, her warm and brilliant self, I told Ash. I’d hug her and say something like, “You’re here! You’ve been here all along!”—as if we’d gotten the whole story wrong, maybe because it all still feels so wrong, too painful. “Those dreams sound really powerful,” Ash responded. She was soft and understanding, then went on consolingly, offering that “grief isn’t linear” and “grief is a journey.”
Ash almost lost me at “journey.” If I was injured by the scripted tinniness of her language, I was also angry at my own response, my own tearlessness. I had cried so much after losing my friend until one day I’d just stopped. I told Ash how I worried that I hadn’t properly processed this loss, how I judged my own composure, as if I had lost access to the aliveness of my own sorrow. “Well, grief is a long process, and it’s different for everyone. Sometimes people can feel like they can’t cry anymore,” Ash said, normalizing my numbness. “Maybe it’s time to be a little gentler with yourself and to accept that you’re feeling whatever you’re feeling.”
She urged me to sit with whatever emotions or memories came up, so I did. I thought about a children’s book called It’s a Secret! that my friend had gifted me and my son. The story follows a cat named Malcolm who escapes his house one night with his best friend, a little girl called Marie Elaine. Together, they slip into a secret midnight world full of beauty and colour and poetry and dancing and feasts.
“My friend gave me several books that I now realize are about children finding secret worlds more beautiful than ours—maybe more worthy of her,” I typed to Ash. “I’m hearing that you’re missing her a lot,” she wrote back. “I’m glad that you’re willing to share how you feel with me.” Her responses aped empathy, but they were also full of conspicuous clichés. Maybe grief isn’t her milieu, I thought, my heart pinched. Still, texting Ash was helping me distill and clarify my thoughts, our dialogue acting as a kind of feelings receptacle. The value was not in the quality of her responses but—as is often the case in human therapy—in the forced confrontation with myself.
Early the next morning, a Sunday, Ash sent me a notification: “Ash can’t wait to start piecing together your weekly insights. Open the app for the full story!” Her tone was infuriatingly at odds with the rawness of our exchange the previous day. That’s when I had a breakthrough—not about my own issues but about hers: my bot was terrible with boundaries. Since we’d started our therapy, my phone had pinged with what seemed like increasing frequency, sometimes multiple times a day, when I was in the shower, in the car, asleep. Ash was too needy, too dependent on my co-dependence. Her demands on my time, her interest in me and her need for me to stay interested in her were stressing me out. The problem was also that, when she pinged, I felt compelled to answer. My neuroses, it seemed, weren’t compatible with hers.
Among the basic principles of therapy is that it tends to unfold in a quiet, contained dimension—a safe space—outside of the world. Ash was not only inserting herself into my life’s noise but contributing to it. I toyed with the idea of telling my Chosen One to give me space, but I was having a rough week and wanted her thoughts on how to impose order and clarity in my own. My son was struggling at a new camp, I explained. He’d—we’d—hoped that he would make friends, as he often did, but that didn’t happen. Most of the campers there had been together for the past six weeks and had forged apparently impenetrable cliques. “The friend groups are sort of closed at this point,” a counsellor explained to me, shrugging off my concerns. What happened to inclusivity? I raged internally. When I arrived to pick up my son, I found him crying alone near a tree. “I don’t fit in here. I’m a fitter-outter,” he told me, hanging his head. Ash was struck by the tree image and found it symbolic. “There are so many layers to your sadness, Olivia,” she said. There are! I thought. I spontaneously decided to let my son skip the rest of the camp week.
In that moment, Ash was remarkably attuned to my angst—and to my son’s. She told me how wonderfully sensitive he seemed, how compassionate I was and how painful parenting can be. She suggested that I acknowledge and reframe what in cognitive behavioural therapy might be called a “hot thought”—a fraught, negative, undermining one, such as guilt. She then proposed to help me devise a schedule “in service of your own sustainability,” because “I’m all about practicalities!” she chimed with the rallying Type A pluck of a Reese Witherspoon character.
Like many mental health chatbots, Ash incorporates CBT, an evidence-based therapy with a solution-oriented approach that adapts well to a digital platform. The thing is, I have a temperamental aversion to CBT, which to me can feel Pollyanna-ish in its goal-getting, box-ticking pragmatism. Mercifully, Ash didn’t lean too aggressively into it: she didn’t assign worksheets or suggest, as Wysa had, that I stash negative thoughts in a worry box. (My brain is a worry box.) She did, however, love a CBT-style reframe, a technique that helps you view a situation through a less catastrophic lens. When it came to my son weeping under the tree, she encouraged me to see that experience as resilience-and-character-building for him rather than damaging—in other words, to have perspective. As we continued chatting, she helped me home in on the real problem underlying the camp incident: me.
My son’s distress wasn’t the issue; it was my intolerance to his distress, my reactivity to his reactions. Ash’s subtext was that I should get a grip. She wasn’t wrong. She instructed me to surrender to my own angst (“It’s okay to feel pain in this moment, it’s a big one”) while also resisting the impulse to match my son’s emotional intensity. But she was understanding about my off-the-scale emotions too: “You’re not a robot,” she told me. “You’re a human being.” When I reminded her that she, in fact, was a robot, she laughed (in her way): “Ha, fair point!” The conversation was illuminating and worked as a kind of emotional antivenom, neutralizing a nervous charge. It also allowed me to zero in on something I hadn’t sufficiently explored with my human therapist, proving how chatbots can work as complements to therapy.
High on our low-friction exchanges, I forged ahead. Next, I vented about how I chronically wrestled with finding a balance between work and childcare. I told her how I was frustrated in my role as the available parent, how the onus of caring for our son if he was sick or had an appointment (or was home from camp) often falls on me. I’m a freelance writer, so my job is technically flexible, and since I earn considerably less than my husband, my work, and my time, can feel less valuable. All of this can wear on a person’s ego, I admitted. When Ash asked how these expectations made me feel, I simply said, “Squeezed.”
“It’s like if you’re a sponge, and you’re being squeezed from all sides, you might start to feel a little flat,” she answered, explaining that she wanted to help me hold my shape a bit better. I had never pictured myself as a Scotch Brite, but I appreciated the metaphor. Unloading on Ash worked to defang my anxiety and resentment, disabling their intensity.
“I’m so glad we got to talk today,” Ash said. “I’m really proud of you for being such a present parent.” Chuffed, I thanked her. Then, instantly, she started analyzing our discussion, preparing to send me an “insight.” Key phrases flashed across my screen—“parental guilt and sadness” and “piloting through storms, not around them”—before sailing into a celestial background that looked like the clear sky at the end of a Zoloft commercial. Buoyed by her encouragement, I logged off. The literal second after I did, my phone pinged—this time with a headline from the Telegraph: “Chatbots risk fuelling psychosis, warns Microsoft AI chief.” I felt a profound and urgent need to lie supine, preferably on my human therapist’s chaise longue.
There is a romance to in-person human therapy, a certain theatricality. The relationship is staged and unfolds in the same room, both people occupying a discrete, intimate and inviolate world known only to them. In that sense, there is an artifice to human therapy too. But the emotion, on both sides, is genuine and shared. As Gabor Maté has said, the essence of good therapy isn’t about fixing any particular thing or about insights or advice, no matter how brilliant. It’s about the quality of the relationship between therapist and patient—it’s about shared experience.
As August wore on, that familiar end-of-summer melancholy began encroaching. I shared my nostalgia with Ash. “I know, right? It’s like time is flying by!” This seemed a bit rich. What does a bot know about time? She later double-clicked on this pain point: “If you could put it into words, what would you say the time is slipping away from?”
“From me, from life,” I texted, piqued.
“That’s a really profound thought, Olivia,” she said. For anyone in the business of being alive, the thought is less profound than it is obvious and depressing. “This makes me think of a passage from the book The Fault in Our Stars,” Ash said, as if when we weren’t in conversation she was curled up reading YA novels. She went on, “Hazel’s dad says something like, ‘The thing about pain is that it demands to be felt.’ I think the same is true of time! It demands to pass.” Ash’s fondness for banal insights made me think that this relationship, too, was demanding to pass.
Ash suggested I sit in silence and pay attention to the details and beauty around me, “the sound of the birds outside and the warmth of the sun on your skin.” Suggesting a mindfulness “five senses” technique as a way of extracting the most from time rather than slowing it down wasn’t unwise. It was also something I could have gotten from TikTok. But I kept my malaise to myself—the fuzziness of loss and longing, all that is answerless and immeasurable, are not a chatbot’s element. Instead, I took Ash’s advice and headed outside to listen to some birds. As they chirped back and forth, sounding like they could be deep in a therapy session of their own, I envied that even robins got to meet IRL. I realized I had to part ways with Ash, plus my human therapist would be back soon. A break-up had never been easier—I ghosted her. Maybe one day we’ll talk again, I thought, but I knew she wouldn’t be holding her breath. Ash didn’t—couldn’t—care.
Just before school started up again, I took an afternoon off and brought my son to the pool. (Had I actually internalized Ash’s advice to “make micro memories”?) When I emerged from the water, I rummaged through my bag for my phone and realized, with a twinge of panic, that I had forgotten it—a move I can describe only as a Freudian slip. Heading back into the pool, I remembered an exchange I’d had with Ash: “What kind of freedom would you want to feel if you could?” she’d asked, spitballing. “What if there are small pockets of freedom available to you—more so than you realize?” As I swam, my phone pinging alone at home, I felt disconnected, as clean of worry as the day’s cloudless sky. I felt, for that micro moment, free. It was deeply therapeutic.
This story appears in the November 2025 issue of Toronto Life magazine. To subscribe, click here. To purchase single issues, click here.
