The beauty industry has always had a front-row seat to human tragedy, the theater of foibles and faux pas that play with hair dye and nail polish. But every now and then, the stylist comes up with a story that reaches a level of absurdity worthy of the center stage. Enter Terry, a self-described “New Yorker” in her late 40s, a woman who comes to the salon a few times a year to vent her grievances and reduce the confusion in her life. (A quick note before we go any further: This story, written by the Observer, is based on a true story from a source who wishes to remain anonymous.)
Picture it: tall, beautiful, blonde, strong, strong enough to get through Manhattan traffic without spilling her coffee. Terry is one of those New Yorkers who “tells it like it is”—as he often reminds me—and “if you don't like his personality, that's your problem.” He's been single for as long as I've known him, which means, consistently, he's had enough romantic blunders behind him to justify a small library. Her love life, or lack thereof, follows her tale of running with her Gen Z colleagues. “How am I going to work with these kids?” he asks, raising his voice to look at the seat next to him. “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 is also the type of person to talk to a lamppost, and I'm sure he has, maybe while waiting to hail a cab. So, when he came in for a routine “makeover” last month and said he had finally met someone, I braced myself. It wasn't his style to be shy about details.
He met her, he announced, on a dating app. She is in her early 50s, divorced with two young children, a demanding job, and a schedule full of business travel. “Tall, dark, handsome—what a man!” (his words) and he was beaten. But, of course, there are contradictions. He is so busy that sometimes he goes days without hearing anything from him. And if Terry takes days without attention, it's a problem. So what do you do? He turns to his confidant, his digital friend: a ChatGPT bot he calls “Sage.”
Yes, the AI chatbot has become Terry's personal relationship coach. Terry, who started using ChatGPT at work to write emails, decided to take things to the next level. He's programmed Sage to be his all-knowing romantic guru, guiding him through the uncertainties of modern dating with the calm, bent wisdom that only a bot can provide.
Whenever she feels neglected or unsure—say, at three in the morning, when she hasn't texted in 48 hours—she reaches out to Sage for advice. “Sage, I didn't hear about him. Is something wrong?” he asks. Sage calmly replies: “He's busy, like he said before. Shouldn't he be in Maryland this week? It is unlikely that he has lost his enthusiasm.” In any other context, this could be the moment when Terry's best friend tells him to breathe, or suggests that maybe he's overthinking. But here, the bot, coded to verify.
And then, as if to show how dependent you are, you tell me how you use Sage to write texts for him, too. “Sage, what would I say if I didn't compliment me enough?” The answer comes with mechanical precision, a careful phrasing to ask for more attention without seeming needy. AI-powered diplomacy, one calculated line at a time.
As she recounts all this from the salon chair, I can't help but wonder: has she gotten her emotions out of the machine? Sage has become the architect of his relationship, the independent counselor who lays out all the answers, shaping his emotional reality. A chatbot is cheaper than therapy, Terry reasons, and it's “between him and Sage”—not that this adds any privacy, given that it all lives somewhere in the cloud.
The deeper he dives into this arrangement, the more surreal it becomes. The Sage now analyzes, suggests and adjusts his relationships, not to mention the delicate balance of when to lean in and when to give him space. Terry doesn't see it as strange; he's just thankful that he doesn't sleep at night thinking about all the texts. But I, scissors in hand, can't help but think this is less about romance and more about letting go of control. He lets the AI play Cyrano, advising him on the basics of human interaction in a way that feels as distant as it is disturbing.
There's a quiet irony in Terry's story—a New Yorker who prides himself on being straight, turning to a machine to manage his emotions, as if love itself needs to be improved. In a world that is constantly outsourcing everything from shopping 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 leaves the salon: is this digital advice a real connection, or is it the beginning of a slow tug of emotional automation?
In the end, does this make our love live less like a fairy tale than exploring technology in sending people out of love? As he tells me the latest updates, I wonder what is left of Terry in his relationship. Is it his voice, his quirks, his humor, or just a polished script created by an invisible digital partner?
I also wonder if he is doing something: Has he found the cure for today? In fact, you're trading a real link for a series of fully coded responses, one AI-generated text at a time. A love story that's equal parts charming and shocking, a reminder that when we seek comfort, we can just lose the machine.
Signed,
Perplexed Purveyor of Split Ends & Secrets in a town where old money drinks bourbon on patios while hipsters brew kombucha in reclaimed tobacco warehouses.
If you have a story to share, please email merin@observer.com.
