I Let an AI App Called ‘Sole’ Stalk My Brain for a Week And It Might Have Saved My Dating Life

The app promised to find my “solemate” in New York by running my late-night chat interactions through an algorithm. It sounded like an intrusive nightmare, but the reality was surprisingly… decent?

I am currently sitting in a dimly lit, overpriced natural wine bar in Lower Manhattan, listening to a woman named Clara explain why she thinks every modern apartment building looks like a corporate prison.

Under normal circumstances, this date would have been preceded by three days of agonizing digital administration. I would have spent a cumulative four hours on Hinge, swiping past photos of guys holding fish or girls doing headstands in Tulum, desperately trying to craft a response to a prompt about “my controversial opinion on coriander” that didn’t make me sound like a clinical sociopath.

Instead, I got here because an artificial intelligence spent seven days essentially interrogating my psyche while I lay in bed in my boxers eating cold leftover takeaway.

Welcome to Sole.

Sole is the latest entry into the increasingly desperate arms race of New York dating apps. Its pitch is straightforward, if slightly alarming: instead of swiping through a meat market of filtered selfies, you spend a week talking exclusively to an AI chatbot. No profile pictures, no bios, no “looking for a long-term relationship, open to short.” Just you, an LLM, and whatever weird, unvarnished thoughts spill out of your head at 11:45 PM.

At the end of the week, the app runs your interactions through an algorithm and generates a single match—your “solemate”—along with a time and location for a blind date.

When I first downloaded it, the experience was deeply uncanny. The chatbot didn’t act like a hyper-efficient digital assistant; it talked more like an attentive, slightly overly-enthusiastic therapist who’d had one too many espresso martinis. It asked me about the last time I cried, what I actually think about my friends’ podcast, and whether I felt guilty about not calling my mum enough.

Because there was no human on the other end to impress, my usual romantic defense mechanisms completely collapsed. I didn’t perform the “breezy, laid-back journalist” persona. I was just a tired guy complaining about the subways, admitting to weird childhood anxieties, and debating the cultural impact of The Sopranos. It felt like screaming into a void, except the void was taking notes on my attachment style.

By day five, the algorithm felt less like software and more like a digital ghost haunting my phone. It knew things about my personality I usually reserve for three drinks deep on a third date.

Then came the drop. Friday afternoon, a notification flashed: Match found. Spring Lounge, Nolita. Saturday, 8:00 PM. Look for the person reading a paperback.

Walking into the bar, my stomach was doing backflips. The sheer lack of visual context felt completely alien. We have been so thoroughly conditioned by the swipe economy to pre-vet our romantic prospects—to scrutinize their height, their taste in music, their posture—that walking up to a stranger based purely on a machine’s recommendation felt like an act of blind faith.

Clara was sitting in a booth, reading a battered copy of a Joan Didion essay collection.

When we started talking, the strangest thing happened: there was no awkward “interview” phase. We didn’t have to do the standard New York preamble about what neighborhood we live in, what agency we work for, or how long we’ve been out of our last relationship. The app had already filtered out the superficial friction. We immediately dropped into a rhythm that felt oddly, unexpectedly intimate.

She told me later that her week with the chatbot had forced her to drop her guard, too. “By the time I got here,” she laughed, taking a sip of orange wine, “I was too exhausted to pretend to be a curated version of myself.”

The traditional dating apps have turned us all into cynical HR managers of our own love lives, endlessly reviewing resumes and rejecting candidates for the sin of having a slightly off-kilter second photo. They feed on our worst, most shallow impulses, keeping us hooked on the gamble of the next swipe while ensuring we stay perpetually single.

Sole is admittedly weird. Handing the keys of your romantic life over to a server farm in California feels like a bleak dystopian concession. But sitting across from someone I actually connected with—without the soul-crushing pre-game of digital flirting—I had to admit the algorithm had done something humans in this city rarely manage to do anymore.

It bypassed the bullsh*t. And in a city as exhausting as New York, maybe that’s the healthiest way to meet someone after all.