The beauty industry has always had a front-row seat to the quirks of humanity, a theater of foibles and faux pas that play out in hair dye and nail polish. But every so often, a stylist stumbles upon a story that hits a level of absurdity that deserves center stage. Enter Terry, a self-described “stereotypical New Yorker” in her late 40s, a woman who comes into the salon a few times a year to air grievances and trim the frizz off her life. (A quick note before we go further: This essay, written by Observer, is based on a true story from a source who wants to remain anonymous.)
Picture it: tall, beautiful, blonde, intense, with the kind of energy that could barrel through Manhattan traffic without spilling her coffee. Terry is one of those New Yorkers who “tells it like it is”—as she reminds me regularly—and “if you don’t like her personality, that’s your problem.” She’s been single as long as I’ve known her, which is to say, perpetually, with enough romantic fumbles behind her to justify a small library. Her love life, or lack thereof, comes in second only to her legendary tales of run-ins with Gen Z coworkers. “How am I supposed to work with these kids?” she asks, voice raised just enough to draw glances from the neighboring chair. “You ask them a question, they don’t look you in the eye. You try to have a conversation, they just blink like you’re interrupting something. This is not how you do business!”
Terry’s also the kind of person who would talk to a lamppost, and I’m certain that she has, probably while waiting to hail a cab. So, when she came in for her usual “shape-up” last month and declared she’d finally met someone, I braced myself. It wasn’t her style to be shy on the details.
She met him, she announced, on a dating app. He’s in his early 50s, divorced with two young children, a demanding job, and a schedule packed with work trips. He’s “tall, dark, handsome—what a hunk of man!” (her words) and she’s smitten. But, of course, there’s a hitch. He’s so busy that sometimes she goes days without hearing from him. And when Terry goes days without attention, it’s a problem. So what does she do? She turns to her confidante, her digital companion: a ChatGPT bot she calls “Sage.”
Yes, an A.I. chatbot has become Terry’s personal relationship coach. Terry, who started using ChatGPT at work to draft emails, decided to take things to the next level. She programmed Sage to be her all-knowing guru of love, guiding her through the uncertainties of modern dating with the calm, detached wisdom only a bot could offer.
Whenever she’s feeling neglected or uncertain—say, at three in the morning, when he hasn’t texted for 48 hours—she pulls up Sage for advice. “Sage, I haven’t heard from him. Is something wrong?” she asks. Sage responds with calm logic: “He’s busy, as he mentioned before. Isn’t he supposed to be in Maryland this week? It’s unlikely he’s lost interest.” In any other context, this would be the moment where Terry’s best friend tells her to breathe, or suggests maybe she’s overthinking. But here, it’s a bot, coded to reassure.
And then, as if to illustrate just how dependent she’s become, she tells me how she uses Sage to compose texts for her, too. “Sage, what should I say if he doesn’t compliment me enough?” The answer arrives with machine precision, a careful phrasing to request more attention without seeming needy. It’s A.I.-approved diplomacy, one calculated line at a time.
As she recounts all of this from the salon chair, I can’t help but wonder: has she outsourced her feelings to a machine? Sage has become the architect of her relationship, a private counselor dictating every response, shaping her emotional reality. The chatbot is cheaper than therapy, Terry reasons, and entirely “between her and Sage”—not that this adds any privacy, given that it all sits somewhere on the cloud.
The deeper she dives into this arrangement, the more surreal it becomes. Sage now does the analyzing, suggesting and smoothing over of her relationship, not to mention the delicate balance of when to lean in and when to give him space. Terry doesn’t see it as strange; she’s just grateful she’s not lying awake at night overthinking every text. But I, scissors in hand, can’t help but think this is less about romance and more about relinquishing control. She’s letting an A.I. play Cyrano, advising her on the basics of human interaction in a way that feels as distant as it does disquieting.
There’s a quiet irony in Terry’s story—a New Yorker who prides herself on being direct, turning to a machine to handle her emotions, as though love itself needed to be optimized. In a world that’s increasingly outsourcing everything from groceries to friendship, why not throw love into the algorithm? And while Sage may keep Terry calm in the wee hours of the night, it also raises a question that lingers long after she’s left the salon: is this digital counsel a true connection, or is it the beginning of a slow drift into emotional automation?
Ultimately, is this making our love lives less a fairy tale than a tech experiment in romantic outsourcing? As she tells me the latest updates, I wonder what’s left of Terry in her relationship. Is it her voice, her quirks, her humor, or just a polished script crafted by an invisible digital partner?
I also can’t help but wonder if she’s on to something: Has she found a modern-day solution? In truth, she’s trading real connection for a series of perfectly coded responses, one A.I.-crafted text at a time. It’s a love story that’s equal parts captivating and chilling, a reminder that in the pursuit of comfort, we might just lose ourselves to the machine.
Signed, Perplexed Purveyor of Split Ends & Secrets
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