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Photograph: By VideoFlow / Shutterstock

Let me tell you—our robot overlords kinda suck at planning a weekend in NYC

ChatGPT is a tourist.

Rossilynne Skena Culgan
Written by
Rossilynne Skena Culgan

"Let Me Tell You" is a series of columns from our expert editors about NYC living, including the best things to do, where to eat and drink, and what to see at the theater. They publish each Wednesday so you’re hearing from us each week. Last month, Things To Do Editor Rossilynne Skena Culgan explored the pure joy of a Mets game.

As the Things to Do Editor at Time Out New York, I’m constantly working to answer one major question: What are the best things to do in NYC this weekend?

I scour the Internet, read posters around town and sort through hundreds of pitch emails to filter for the coolest, quirkiest, funnest events in New York City. It takes a lot of time, so I decided to try out ChatGPT and see if it could help me (and you!) plan a perfect weekend. 

After all, the free online program is writing college papers, solving complicated tax issues and creating poetry. With all of those abilities, I figured the chatbot could help me figure out how to spend my actual human time on Earth. Not quite.

I started out by asking OpenAI’s chatbot a simple question: “What should I do this weekend in NYC?”

It told me "there are numerous activities you can enjoy in NYC this weekend." OK, accurate.

Then, it recommended a list of 10 popular options to explore: Central Park, museums, the High Line, Broadway, Times Square, harbor cruises, Chelsea Market, the Statue of Liberty, street food and local events.

All great things, sure, but a pretty generic, quite touristy list. I decided to push further by asking, "You mentioned local events. What specific events are happening in NYC this weekend, May 19-21?"

That’s when the bot fizzled out like a MacBook with water damage.

ChatGPT chat bot screen seen on smartphone and laptop display with Chat GPT login screen on the background. A new AI chatbot by OpenAI. Stafford, United Kingdom, December 13, 2022.
Photograph: By Ascannio / Shutterstock

It replied: "As an AI language model, I don't have real-time information or access to current event listings. I apologize for any inconvenience caused. To find specific events happening in NYC during the weekend of May 19-21, I recommend checking online event platforms, local event calendars, or websites of popular venues in the city."

All right, let’s continue to push.

“What event platforms and local news sites would you recommend?” I asked.

And here’s where my job security comes in: Time Out New York was among its recommendations for online event platforms and local news sites, alongside Eventbrite, The New York Times, Gothamist and a few others.

Feeling the love from the bot, I gave it another chance to redeem itself, deciding to ask about the best things to do in Central Park. It performed a little better here, suggesting to "take a leisurely stroll" and "visit iconic landmarks" like the Bow Bridge and Strawberry Fields. Truly some of my favorite places but not necessarily a nuanced take on how to spend a weekend in New York City.

Specificity seemed to work for our robot friend, so I tried one more question: What should I do on a date in NYC?

The answers weren’t half bad here, including visiting rooftop bars The Press Lounge and Westlight (two of my favorites), taking a cooking class or visiting a jazz club like Blue Note (again, well done). ChatGPT also recommended watching the sunset at scenic spots like Hudson River Park or Brooklyn Bridge Park where you can "enjoy the magical colors." Big claim from a robot but also accurate.

It also adorably and wisely cautioned to "Remember to consider your date's interests and preferences when choosing an activity, and be open to creating a unique and personalized experience that both of you will enjoy."

Skyline of New York City Financial Downtown Skyscrapers at sunset. Manhattan, NYC, USA. View from New Jersey. Decentralized economy. Blockchain, cryptography and cryptocurrency concept, hologram
Photograph: By VideoFlow / Shutterstock

Perhaps I shouldn’t judge ChatGPT so harshly as the Ask Jeeves of the 21st Century. Of course, it doesn’t know how to do things outside of the house. Its favorite pastimes include hanging out at home doing creepy stuff. Plus, it has limited knowledge of the world after 2021 (lucky little creature). AI tools will likely get even better over time, especially if they can digest current events—and if that happens, the landscape for journalists (and all of us, frankly) becomes even scarier. 

So before ChatGPT comes for all our jobs, I had to indulge my curiosity and ask about one of its recommended sites for events: What is Time Out New York?

I swear I wasn’t holding a gun to its metallic robot head when it answered this question. Here's the response:

"Time Out New York is a widely recognized and respected media brand that provides comprehensive information about events, entertainment, dining, and culture in New York City. … Whether someone is looking for new dining experiences, seeking recommendations for weekend activities, or wanting to stay up-to-date with the cultural scene, Time Out New York is a valuable resource for discovering and enjoying the vibrant offerings of the city."

Not exactly love letter material, but we'll take it. And now we'll take you to an actually helpful link of things to do this weekend in NYC, updated every week by an actual human right here in New York. 

Finally, we'll leave you with a haiku created by ChatGPT about NYC. Echoing the whole experience, it's not great, but it's accurate.

City that never sleeps
Skyscrapers touch the skyline
Dreams pulse in its heart.

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