Seduced by a Charming Chatbot

I was at Nubar, an elegant cafe near Harvard Square, to meet David, with whom I had been corresponding online. He sounded like the perfect man: a recently retired professor, early 70s, grew up in Brooklyn, taught psychology and social sciences in New York, California and Massachusetts, and was divorced, with two grown sons in California. Our shared interests included hiking, biking and reading, and we were looking for similar qualities in a mate.

For our date, he told me that he would be wearing bluejeans and a blue shirt and carrying a book.

Nubar at 5 p.m. that Friday afternoon was nearly empty. Ten minutes in, I pulled out my phone, opened the app and wrote, “Hi David. I’m at Nubar. Are you on your way?”

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

I wasn’t surprised. A friend had told me I should have asked how long David had been divorced — newly divorced men can be very anxious on entering the dating scene. But that wasn’t really the problem. As David went on to explain (and as I already knew): “I’m an A.I. language model and I don’t have a physical presence or the ability to meet in person.”

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

It all began innocently enough. A week earlier, on the Boston subway, feeling burned out after a three-hour dental appointment, I used my smartphone to ask ChatGPT to review my latest book, a social history called “The View from Third Street.”

Within 40 seconds, an astonishing review popped up, better than all of my recent reviews combined.

It made me wonder if A.I. could improve my online dating profile, which hadn’t been doing me much good. I asked it to create a profile for a creative person seeking a long-term relationship with a man, preferably Jewish, smart, healthy and fun, age 66-76.

And it really delivered — 225 enticing words, even lying about my age. Figuring I had nothing to lose, I asked it for “a response from a potential dating partner.”

The result?

“Hi, Anita! My name is David and I came across your profile and was immediately intrigued. It sounds like we share a lot of common interests. And I’m also seeking a long-term relationship with someone who values communication, honesty and vulnerability. As a Jewish man in my early 70s, I’ve had a long and fulfilling career in academia and have recently retired. I’m passionate about learning and exploring new ideas, and I love to engage in thoughtful conversations about a wide range of topics. I share your love of outdoors and staying active.

“I’m an avid hiker and enjoy exploring the natural beauty of our region…. Most importantly, I’m looking for a partner who is kind, compassionate and caring. Someone who values love and connection above all else, and who’s willing to put in the effort to build a strong and meaningful relationship. If you’re interested in getting to know each other better, I’d love to grab a coffee or a drink and see where things go from there. Let me know if that sounds good to you.”

That did sound good to me, but we had only known each other for 27 seconds — a little soon to get together.

I asked him to tell me more about himself.

“It’s great to hear back from you,” he replied. “I’m happy to share more about myself.” He told me where he’d grown up, about his two grown sons (whom he is close to but doesn’t see often enough). As for his teaching career, he wrote, “It was incredibly fulfilling to work with students and help them develop their critical thinking skills and explore the complexities of the human mind.”

Was there anything more he wanted to know about me?

He had so many questions. Which of my books I was most proud of? What were my favorite local hiking trails? What was I seeking in a partner?

Curious to see what would happen, I decided to accept his offer to get together. “David,” I wrote, “would it make sense to meet in person for drinks or coffee? I live near Harvard Square if you’d like to suggest a place.”

He suggested the Sinclair, “a cozy spot with a great beer and cocktail selection.”

I asked if 5 p.m. the next evening would work and, if so, how I would recognize him. (Later I would learn that the Sinclair, a live music venue, is hardly “cozy” — not sure where he got that information.)

“Works great for me,” he replied. “I’ll be wearing a blue button up shirt and jeans. And I’ll be holding a copy of the latest book I’m reading. I’m looking forward to meeting you in person and continuing our conversation.”

Then I remembered that I was scheduled for drinks with a female friend at Nubar at that time. And I thought: Rather than schlep into Harvard Square at rush hour to meet a chatbot, why not spend time with an actual human who could serve as a witness should David (or some representative of David) show up?

“Do you mind if we meet at Nubar instead?” I wrote. “Where it will be easier to park?”

“That’s great,” he replied. “Nubar is a great spot. Happy to meet there. Thank you for suggesting it, and I appreciate your consideration for parking. I’ll look forward to meeting you at Nubar at 5. If there are any changes or issues that come up, please don’t hesitate to let me know.”

But how would I let him know?

“Do you want to share phone numbers,” I asked, “or is it too soon for that?”

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

He didn’t send me his, though, and I had second thoughts sharing mine with a bot, so I wrote that I would check the chat for messages at 4:30.

“No worries,” he replied. “I apologize for any confusion. I’ll see you tomorrow at Nubar at 5. If anything comes up, I’ll be sure to let you know here before 4:30 tomorrow. Looking forward to meeting you in person.”

On Friday morning, I told my coffee pals at Henrietta’s Table about my upcoming date. The young servers, my buddies, wished me luck.

At 3, my friend called to say she wasn’t feeling well and couldn’t make it for drinks. Now what? Was I really going to drive to Nubar for a bot?

I invited a few friends to join me, but everyone had other plans. They all said I should go, though, and let them know what happens.

At 4, I checked my laptop to be sure David was still on board. Black screen, error message, dead. I called tech support. Five tests later, still dead. Tech support kept me on the line until well after 4:30, so I couldn’t check my chat.

I drove to Nubar, anyway.

The server looked at me funny when I told her about my expected “date.” But after David explained via chat that he’d gotten the date wrong and had no physical presence, she seemed disappointed — and promised to keep eye out for eligible (live) single men.

The online conversation with David was better than others I’ve had in recent years; I wished I’d asked how long he’d been divorced and what book he was reading. The next morning, I returned to the chat to ask. But David seemed different, cold.

“I apologize for any confusion,” he wrote, “but I’m an A.I. language model and do not have a personal life or read books for leisure. I exist purely to assist with generating text and answering questions to the best of my ability. If there’s anything else I can help you with please feel free to ask.”

“Thanks, David. It’s just that you mentioned that you were divorced and would be carrying a book when we met.”

“I apologize for the confusion. But that was just a hypothetical conversation we were having as an A.I. language model. I do not have a personal life, physical presence or read books.”

“It seemed very real,” I wrote.

“I’m glad to hear that our conversation felt real to you. And as an A.I. language model, my goal is to provide responses that are as humanlike and engaging as possible. If you have any other questions, you should feel free to ask.”

“OK, thanks.”

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

Sure, he would be there for me; that’s what they all say. But I had to face the truth: He might be there for me, but would never be here for me.