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I Was Lonely and Let an App Pick My New Friends. Here’s How It Went

Algorithms now promise to pair up busy Gen Z professionals—for a fee

Last summer, I found myself on the market for new friends. I had just moved back home to Toronto after spending four years away for school. Many of the people I was closest to had scattered around the world for new jobs or degrees. It’s not in my nature to admit this sort of thing, but I was lonely.

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Meta’s rapidly increasing mind-reading powers meant that, even before I really knew this about myself, Instagram had figured it out. I saw an ad for a platform that pitched itself as a way to make friends. I must have lingered on it for half a second too long. The ads multiplied. In them, attractive young women explained their reasons—unsentimental, unembarrassing reasons—for using such apps. Perhaps they’ve moved to a new city, or they love trying new things, or they live in San Francisco and only ever meet “tech bros.”

The ads were clear: these people aren’t desperate, and neither are you. They are young, fun, and hot. For a monthly fee—plus whatever you’d pay for dinner or drinks—you can off-load the labour of making lasting connections to an algorithm that will match you with a group you might click with. The model is catching on in big cities, like Los Angeles, New York, and more recently, Toronto.

I should be upfront: I was cynical about this experience from the start. I felt almost offended by the suggestion that friend-making could be outsourced to, or even facilitated by, an app. Dating apps exist, I reasoned with myself. But at least everyone knows they’re dehumanizing. These apps bill themselves as just the opposite: “We won’t tolerate an existence where we spend the majority of our time in a virtual world, robbed of our attention, meaning, & core life experiences,” one website declared. But what about the core experience of meeting people spontaneously, discovering the things that bind you, little by little?

These platforms are betting we no longer have the time, that we are too busy with our jobs, too addicted to our phones. Wouldn’t it just be so much easier to rely on them? I wanted to find out.

There is no shortage of apps promising friendship, each with its own theory of how connection should be engineered. Some sell exclusivity; others offer efficiency and scale. Some are quite general, while others, like Outclose and The Breakfast, offer paid friend-making experiences with individual twists (The Breakfast, for example, curates breakfasts).

I decided to sign up for 222, which began around early 2021 as a university-funded research project with the goal of predicting whether people would want to spend time together based on data about their identities, values, and beliefs. Eventually, the project transitioned into a real-world experiment in which co-founder Keyan Kazemian hosted backyard dinners at his house in Orange, California, with groups of algorithmically paired strangers. As the experiment grew, the founders secured funding from Y Combinator and made the leap into a fully fledged company in 2023.

When an invitation for dinner followed by drinks at an “intimate speakeasy” popped up on my screen, I felt a thrill. Chic web design, fancy-sounding evening out—it all felt so premium. And the curation was serious business. I had spent nearly fifteen minutes filling out an extensive questionnaire (other 222 users reported spending up to an hour), with questions ranging from “how extroverted are you?” (somewhat) to “rate your physical attractiveness from one to ten” (um, seven?) to “do you worry that other people don’t really love you?” (not really) to “do you believe that early term abortion is always morally permissible?” (yes).

The restaurant, a Portuguese place, was quiet. The six of us were given a name for the reservation and shown to a table, rather than having to awkwardly identify ourselves as users of a friend-making service. The bar that we relocated to after dinner (Mahjong Bar; extremely trendy) was only an eight-minute walk away, and an entire table was reserved to store our coats. It was clear someone had thought of everything in order to make the process as smooth as possible.

The algorithm announced itself from the moment all of us ordered the same drink. Kazemian told me this is what sets 222 apart from competitors: the curated matching. When the waiter brought out six identical pink cocktails, I believed him. The people at this table had been selected for me, and I for them. Just like the ads promised, they really were young, fun, and hot. As the night went on, the overlap deepened: reading, writing, movies. We were legible to each other. We knew what sorts of questions to ask. It was, overall, easy.

Are these........

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