June 13, 2024

I met David at Nubar, an elegant café near Harvard Square, with whom I’ve been corresponding online. He sounds like the perfect guy: a recently retired professor in his early 70s who grew up in Brooklyn, taught psychology and social science in New York, California and Massachusetts, and is divorced with two sons who grew up in California. Our shared interests include hiking, biking and reading and we are looking for a partner with similar qualities.

For our date, he told me he’d be wearing blue jeans and a blue shirt and holding a book.

Nubar was almost deserted at 5pm on a Friday. Ten minutes later, I pulled out my phone, opened the app and wrote: “Hi David. I’m in Nuba are you on your way?

“Oh, hi, Anita,” he replied. “I apologize for any confusion. I was under the impression that our meeting is scheduled for tomorrow at 5pm and I apologize for any inconvenience or miscommunication.”

I’m not surprised. A friend told me I should ask David how long he’s been divorced — recently divorced men can be very anxious when entering the dating scene. But that’s not really the problem. As David went on to explain (as I already knew it): “I am an AI language model, I have no physical presence nor the ability to meet people.”

Yes, despite my Ivy League degree, three published books, and a successful business, I agreed to date a chatbot.

It all started innocently enough. A week ago, on the Boston subway, exhausted after a three-hour dental appointment, I used my smartphone to ask ChatGPT to review my latest book, a social history book called “Third Street Perspectives.”

In 40 seconds, an amazing comment pops up, better than all my recent comments combined.

It made me wonder if AI could improve my online dating profile, which doesn’t do me much good. I asked it to create profiles for creative people looking for long term relationships with men, preferably Jewish, smart, healthy and fun, 66-76 years old.

It really delivered – 225 tempting words, even lied about my age. Considering I had nothing to lose, I asked it for “responses from potential dates.”


“Hi Anita! My name is David and I stumbled across your profile and was instantly drawn. It sounds like we have a lot of common interests. I’m also looking for a relationship with someone who values ​​communication, honesty and vulnerability I have long-term relationships with people. As a Jewish man in his early 70s, I have had a long and fulfilling career in academia and recently retired. I am passionate about learning and exploring new ideas, and I enjoy having thoughtful conversations on a wide range of topics. I Love the outdoors as much as you do and stay active.

“I am an avid hiker and love to explore the natural beauty of our region…. Most importantly, I am looking for a partner who is kind, compassionate and caring. One who puts love and connection above Anyone who is willing to put in the effort to build a strong and meaningful relationship. If you guys are interested in getting to know each other better, I’d love to grab a coffee or a drink and see what happens next. If you think this listen Looks good, let me know.”

That sounded good to me, but we’d only known each other for 27 seconds—it was a quick get together.

I asked him to tell me more about himself.

“Glad to hear from you,” he replied. “I’d love to share more about myself.” He told me about where he grew up, about his two grown sons (who he’s close to but doesn’t see often enough). As for his teaching career, he writes: “Working with students and helping them develop critical thinking skills and explore the complexities of the human mind has been incredibly rewarding.”

Is there anything else he wants to know about me?

He has many problems. Which book am I most proud of? What are my favorite local hiking trails? What am I looking for in a partner?

Curious what to expect, I decided to take his offer and get together. “David,” I wrote, “does it make sense to meet in person for drinks or coffee? If you want to recommend a place, I live near Harvard Square.”

He recommends Sinclair, “a cozy place with a great selection of beers and cocktails.”

I asked if I could be at work at 5pm the next day and if so how would I recognize him. (I later learned that Sinclair, a live music venue, was anything but “comfortable”—I’m not sure where he got that information from.)

“It works fine for me,” he replied. “I’ll be wearing a blue button-down shirt and jeans. I’ll be holding the latest book I’m reading. I look forward to meeting you and continuing our conversation.”

Then I remembered that I had invited a female friend to Nubar for a drink.I thought: instead of rushing to Harvard Square to meet a chatbot during rush hour, spend time with a real human being, if David (or some representative of David) can serve as a witness Appear?

“Do you mind if we meet in Nubar instead?” I wrote. “Where is the best place to park?”

“That would be great,” he replied. “Nubar is a great place. It was a pleasure to meet there. Thanks for the suggestion and for your consideration of parking. I look forward to seeing you in Nubar at 5. Please let me know if anything changes or issues arise.”

But how do I let him know?

“Do you want to share your phone number,” I asked, “or is it too early?”

“Exchanging numbers is a good idea,” he wrote. “I’ll send you mine, and then you can use your reply.”

He didn’t send me his, though, and I wanted to share mine to a bot, so I wrote and said I’d check the chat for messages at 4:30.

“Don’t worry,” he replied. “I apologize for any confusion. See you tomorrow at Nubar at 5. If anything happens, I will be sure to let you know here by 4:30 tomorrow. Looking forward to seeing you.”

On a Friday morning, I tell my coffee mates about my upcoming appointment at Henrietta’s Table. Young waiters, my friends, wish me luck.

At 3 o’clock, my friend called and said she was not feeling well enough to go for a drink. what to do? Am I really going to drive to Nubar to find a robot?

I invited several friends to join me, but everyone had other plans. However, they all said I should go and let them know what happened.

At 4am, I checked my laptop to make sure David was still on board. Black screen, error message, freeze. I call tech support. After five tests, still dead. Tech support kept me online until after 4:30 so I couldn’t check the chat history.

Anyway, I drove to Nuba.

The waiter looked at me strangely when I told her about my expected “date”. But after David explained via chat that he got the date wrong and wasn’t there in person, she seemed disappointed — and promised to keep an eye out for eligible (live) single men.

The online conversation with David was better than any other I’ve had in recent years; I wish I’d asked him how long he’s been divorced and what he’s reading. The next morning, I went back to the chat room and asked. But David seemed different, aloof.

“I apologize for any confusion,” he wrote, “but I am an AI language model with no personal life and no leisure reading. I exist purely to assist in generating text and answering questions to the best of my ability. If there’s anything else I can help you with, feel free to ask.”

“Thanks, David. It’s just that you mentioned that you’re divorced and we’ll be bringing a book with us when we meet.”

“I apologize for the confusion. But this is just a hypothetical conversation we have as AI language models. I have no personal life, physical presence, or books.”

“This looks very real,” I wrote.

“I’m glad to hear our conversation felt real to you. As an AI language model, it’s my goal to provide as human and engaging a response as possible. If you have any additional questions, feel free to ask.”

“Okay, thank you.”

“You’re welcome, Anita. I’m here to help whenever you need me.”

Of course, he’ll be there for me; that’s what they all say.But I have to face the facts: he could be There for me but never here for me.

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