This is what happens when AI sets up L.A. strangers on a friend date

It’s a Tuesday night and I’m scootering through Hollywood to have dinner with five complete strangers. I’m wearing my “nice” shirt and loafers because this feels almost like a blind date, even though I’ve been assured it’s not; it’s a “chance encounter,” curated by the AI-powered social events platform 222.

Born out of backyard dinner parties with seating charts determined by personality questionnaires, 222 was founded mid-pandemic by three Gen-Zers to facilitate meaningful experiences with new people, in new places. The website defines the platform mostly by opposition: It’s not a dating app, not a friend-making service, not networking, not mindless scrolling, not even the metaverse (thank God). Rather, the website says it’s an “experiment” that pairs strangers together for in-person activities based on personality tests — like a modern-day eHarmony, but for community-building, with some AI and event planning mixed in, I gather. Whatever it is, it promises me “an experience unlike anything before.”

A few weeks back, 222’s targeted Instagram ad disrupted my doomscroll with grainy footage of pretty people laughing on a rooftop under string lights (they got me good!). Before I knew it, I’d spent 10 minutes answering questions about how I see myself and the world around me. On a scale of 1 to 7, I ranked statements such as “I worry that other people don’t love me” and “I believe comedy is becoming too politically correct.” The survey felt so long and invasive (another question: “How attractive do you consider yourself?”) that I almost quit, wondering who exactly was harvesting my data, and to what sinister end? But I was in too deep. After specifying my desired neighborhoods and activities, I finally reached a results page where I was told my personality type is the “experientialist.” This seemed a bit on the nose, seeing as I had just clicked the ad promoting … experiences.

I probably would have forgotten the whole thing had 222 not texted me every few days thereafter with invitations to bespoke experiences throughout the city: a karaoke night at an ’80s-themed speakeasy, paint and sip at a beachside wine bar, line-dancing lessons at a “vintage” Western saloon, billiards at a dive bar that also — would you believe? — serves natural wine. The possibilities seemed endless. Ignoring these texts had a compounding effect of making me feel like I was being ungrateful, like I wasn’t opening myself up enough to the universe. I’ve lived in Los Angeles for eight years and have recently found myself saying sentences like, “The pandemic really killed L.A.’s social scene,” as if I’ve studied the data, or even had a thriving social life prior to lockdown. I know it’s unattractive to complain without taking initiative, so when another text came through with an invitation to dinner and a jazz night (on a rooftop!), I hunkered down, replied “YES,” and paid the $17.22 “curation fee” without hesitation. I was choosing chance, baby.

That is, if 222 chose me back. There’s a vetting process, apparently, and I’d be notified day-of if I was selected. A smart move, as this gave me the impression that the AI was hard at work crunching the numbers, carefully curating the alchemy of the evening. Or maybe it was just seeing if enough people RSVP’d to qualify. Regardless, when I got the text confirming that I’d been chosen, I couldn’t help but feel, forgive me, special.

The night arrives. I park my scooter outside the designated location, Grandmaster Recorders, and reread the detailed instructions that were texted to me that morning. I’m a few minutes early, so I stand on the sidewalk and pretend I have urgent business on my phone while I scope out the joint. Eventually, I hear a guy tell the doorman, “I’m here for the 222 event,” and I follow him inside. I introduce myself and he tells me, with a proud smile, that it’s his third 222 outing. I feel a sense of hope as the host guides us to our assigned seats.

The restaurant is virtually empty (it’s early, and it’s a Tuesday), but I spy a few half-filled tables in the corner, peppered with an eclectic mix of young people. This must be us. I’m seated at a booth with three women who don’t seem to have been talking much. We exchange introductions between nervous glances at the two remaining open place settings. In the center of the table, 222 has left an envelope filled with question cards and a disposable camera that suggests we’ll be making memories tonight we’ll never want to forget.

Our server takes our drink orders and I wonder what she thinks of us (losers?). I order a martini. The women beside me order mocktails. “I’m on a fitness journey,” one explains. I learn that they’d come as a pair (we were allowed a plus-one), they live on the Westside, and they’d met a few months ago at a beach clean-up. I swear I’ve been meaning to do one of those.

Two men approach our table with their hands in their pockets. They, too, seem to have chosen their “nice” shirts. I look to see if the women beside me are excited by the reveal of what could be two eligible bachelors (I sure am!), but they give nothing away. Maybe we really are here just to make friends.

We do another round of names with the optimistic air of a freshman orientation group, except now we’re swapping “What are you studying?” for the dreaded “What do you do?” The setup also gives us some conversational fodder. How did we hear about this? Instagram, TikTok. Wasn’t the survey long? Terribly. Do you remember your results? Some are “experientialists” too, some “romantics,” others couldn’t recall. A few note they had ranked “comfort” low on the scale of what’s important to them. “With comfort, there’s no growth,” one says. “Totally,” another nods, “hey, maybe that’s why the algorithm put us together!”

Naturally, we have dinner. The food is mediocre at best, but we soldier on. As we uncover our commonalities, we wonder if they’re coincidence, or if we have 222’s AI to thank. We’re all around 30 years old (phew, I’d read somewhere that they used to cap participants at 27). We’re all single (“Imagine someone in a relationship doing this!” we laugh). Half the table had quit their corporate jobs recently, or were planning to soon. I find out the guy beside me works for my former employer. And, placebo or not, I can’t help but think there are other, less discernible compatibilities uniting us all.

No one is on their phones for once. It’s nice. There’s an openness to the conversation. People aren’t afraid to say sentences like, “The planet has chakras,” and, “I’m trying to increase the ‘wowness factor’ in my life.” It’s as if, by signing up for this strangeness, we’ve already admitted that we’re seeking deeper connections. We’ve freed ourselves to venture off-script.

Only a few times throughout our meal are there total silences that make me want to die. During one of these lulls, someone reaches for the cue cards. We implicitly agree these are cheesy, but we do them anyway. One reads, “What’s a story from your life that sounds like a lie but is absolutely true?” Someone blurts out, “One time I saw a penguin walking through LAX!” Surely we never would’ve gotten here on our own.

Almost two hours pass, mostly without pain, before the bill drops and panic ripples across the table. “222 is paying for this, right?” I joke. It’s certainly not cheap, and our ordering was disproportionate, but we split the tab evenly like the 30-year-olds that we are.

For next steps, we look to our phones, where we’ve received directions to the second location, Bar Lis, just a short walk away. 222 has removed the burden of planning and decision-making, and we follow like sheep. Before tonight, I had imagined bailing during this moment of transition, but now I wouldn’t dare. I’ve come this far. I must #exploreserendipity.

We skip down Sunset Boulevard with a lightness in our loafers (or perhaps just my own). When we arrive, we tell the bouncer we’re with 222 and it feels almost like we’re VIPs. We take the elevator to the rooftop bar, which offers a view of downtown. A jazz band is warming up. There are string lights. The host guides us to a lounge section that 222 has reserved for us. She explains that Bar Lis normally charges a minimum per head (gasp), but since we’re a big group we can just order at the bar (crisis averted).

In line for my second martini, I hear one of the guys confide that he has a first date on the way. “Does she know about us?” I ask, amazed. He blushes and shakes his head. I guess you can’t always trust chance alone; sometimes you have to take out an insurance policy.

Other 222 groups trickle in, and we suppose we should make an effort to mingle. I meet more nice people who seem to be having a great time. One tells me their cohort has labeled itself the “Tender Hearts Club” after discovering that they’d all recently gotten out of long-term relationships. Did the AI somehow sense this? Two of them have already paired off, their knees touching in the corner.

The jazz band is playing a cover of “Break My Soul,” in honor of Beyoncé’s birthday. Our group meanders to the balcony to admire the view. The glowing cityscape turns us pensive, and we marvel at our good fortune. Someone whispers, “I think we had the best table of the bunch.”

I don’t see any other gay people, and I begin to plot my exit. I’m not having a bad time, I just feel I’ve gotten my fill of chance for the evening. As if reading my mind, a woman from my table initiates goodbyes. We exchange Instagrams and realize we have no mutuals. We must come from different planets. On our way out, we giggle and wave to the guy on his date. They look happy, we think.

I’m about to hop on another scooter when the Westsiders offer me a ride home. As I duck into the backseat, I hear my mother warn, “Never get into a car with strangers!” But I remind myself, it’s OK. I feel safe. We’re no longer strangers, right?