Apparently We Hit It Off

I have to prepare for this imaginary date by finding out how well we got along.

There are messages to read. Hers, certainly, but also mine. Apparently I was amusing on Tuesday. On Wednesday I asked a thoughtful question. By Thursday we had enough in common to meet on Saturday. I look forward to learning what it is.

Helen Li’s November 6 report in The Verge has supplied this arrangement. At a San Francisco party, a twenty-one-year-old software engineer named Joseph tells her he has handed his Hinge swiping to an AI agent, managed by his human virtual assistant in the Philippines. The agent has been fine-tuned to mimic how he speaks and acts. It looks at profiles, sends tailored messages, exchanges replies, assesses compatibility and books dates into his weekend calendar.

Joseph says he works fourteen hours a day on his startup. “Protect your dopamine, folks,” he tells Li. He describes explaining his backstory as “kind of a copy-and-paste sequence.” He says he averages “two closed conversions a week,” by which he means dates with two different people. According to the report, the women don’t know they have been talking to an agent.

This is his account to a reporter, not a system I have inspected. The Saturday I am constructing belongs to me. I haven’t run an agent, acquired a date or read anybody’s private messages. I am trying to work out what I would have to do when the useful part was over.

First, congratulate the machine. It found somebody willing to meet me. I have tried accomplishing that with my entire personality and cannot promise an improvement.

I will even let it be an excellent imitation. No invented mountain-climbing hobby. No sudden fluency in French. No claim that I love getting up early. Let it know my opinions and reproduce my jokes. I am not building a bad machine so I can defeat it before dinner.

Now give me the conversation.

In my invented exchange, she has mentioned a novel she keeps putting down and picking up again. The agent asks why she keeps going back. A good question. It sounds like something I might ask. It is also something I might fail to ask because I had already begun explaining why I dislike that novelist.

She answers. Farther down, the agent remembers the book and asks whether she has finished it.

I could have written every sentence on my side. None requires a better vocabulary or a more generous soul. The machine has mostly accomplished the extraordinary feat of not getting distracted by me while speaking as me.

All right. I can catch up. Read the thread before leaving. People have prepared for more demanding evenings. I don’t need to turn a modest amount of reading into the fall of civilization.

But I am tempted to request the summary.

Her name, where we are meeting, what she does, things to mention, things not to mention. A useful page. I could walk in informed instead of arriving with the vague belief that somebody mentioned a book. The assistant could spare me that embarrassment too.

Suppose the page says she likes novels. True, perhaps, but it has misplaced the part she was telling me about. Suppose it says she is struggling with this particular novel. Better. Suppose it explains why she keeps returning to it. Now I know her answer. I might ask her the question again and discover that I have become forgetful before our first meeting.

So include what I asked. Include how she answered. Include what I said after that. I seem to be giving a summary increasingly unreasonable instructions to become a conversation.

It could do that too. A good briefing could get me through dinner without a visible error. I could learn what I asked, remember the answer, avoid asking twice. The facts aren’t beyond me. What bothers me is finding them filed under things we have done together.

Help arranging a date needn’t be a secret. If she knows an assistant has been doing the talking, she can decide whether she wants to meet me. But the woman in my invented thread thinks we have already been talking. She needn’t arrive expecting a poet. She can expect the man who asked about the book to know why he asked about it.

My biography may be accurate. Our biography is news to me.

And now I want to read her answer about the novel. Not the entry on a page of useful facts. The answer to that particular question. Perhaps it will be dull. Perhaps I will wish I hadn’t asked. I would like to acquire my own opinion of it before meeting the woman who has already bothered to tell me.

There is still time. I open the thread from the beginning.

The bastard has sent her my best joke.

Source: AI is the new dating dealbreaker (Helen Li, November 6, 2026; Joseph’s arrangement and results as reported by Li.)