My first Timeleft date went horribly wrong

Kidding, it was kind of great and gave me a shred of hope for human reconnection.

Last night I did something drastic: I went out.

I’ve been something of a recluse since returning to New York a year ago. Before making the move to be closer to my son, I had retreated from alcohol and dating and pretty much every other social norm.

Since then, I’ve had little interest in getting out of my sanctuary in the Bronx. My friends are all scattered, living in different states and on different continents. The solitude has been good for me, but I was also slipping into enjoying it a little too much.

So with my son with his mom for this part of the summer, I realized I needed a healthy distraction outside these walls.

I remembered Timeleft, an app I encountered on Instagram sometime last fall. It puts strangers together for dinner based on their budgets and preferences. At the time I wasn’t ready for interaction, got only as far as the questionnaire thing, and forgot about it. (I say forgot, but after that initial click you’re relentlessly spammed with ads until you eventually give in.)

“Everybody needs a friend,” Bob Ross gently chants as I write this, his broad strokes manifesting happy little trees. (How am I only now discovering The Bob Ross Channel on Freevee?)

Anyway, I took the train to the Flatiron and walked to the appointed restaurant. I wasn’t nervous, though I had a twinge of anxiety when I found the table empty. Punctuality is no great asset when you’re the first to arrive.

Spoiler alert: The others showed up and dinner went fine. There are no wild anecdotes, no meltdowns over politics to share, just four people meeting face-to-face outside their comfort zones.

We were sitting and eating among strangers, but were we really? I’d offer a more nuanced description: curated strangers. The Timeleft experience is based on whatever personality traits we choose to feed the algorithm, which means we’re not truly strangers, if only because we shared the notion to sign up for this.

Meet my curated strangers, whose names I have changed, in order of arrival:

• Mike: white cis male, 40s, software engineer from Los Angeles

• Josie: white cis female, 40s, cancer survivor from New York

• Amy: Chinese cis female, 40s, college art teacher from Beijing

AI scares the hell out of me. The concept feels something like staring down an oncoming freight train while helplessly flailing my arms. In just a couple of years it seems our freewill, our livelihoods, and so much more are slipping away — with our flagrant permission and all-too-eager encouragement. And there’s no going back.

That said, the Timeleft algorithm did something unexpected, which dawned on us when nobody at the table ordered drinks: We were grouped based on our mutual decision to abstain from alcohol. Nice touch. It opened up the conversation among curated strangers who otherwise might have struggled to dive in.

In this way, the algorithm helped us establish common ground. Over sushi we talked about where we’ve traveled, what we’ve been reading, what we’re listening to. And as the only parent at the table, I still did plenty of bragging about my son.

Amy spoke the least but said the most: “It doesn’t matter what happens or if we get along, it will be a beautiful experience.”

And that’s what it was. No pressure, no drama, no commitment. And we agreed it’s something we’d be up for trying again.

So after a couple of hours, when the conversation began to peter out, I suggested that we leave it on a high note. The four of us drained our water glasses and went our separate ways.

It was good to get out again, and to go home.