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Home»Tech»I Asked ChatGPT 500 Questions. Here Are the Ads I Saw Most Often
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I Asked ChatGPT 500 Questions. Here Are the Ads I Saw Most Often

Press RoomBy Press RoomMarch 27, 2026No Comments4 Mins Read
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OpenAI is starting to stuff the free version of ChatGPT with ads. So, I spent this week asking ChatGPT 500 questions on the mobile app to get a sense of how these new ads look as they roll out to more users in the US. My questions were loosely based on how OpenAI says people use its generative AI tool, like for seeking information or requesting practical guidance.

In my rough tests, the ChatGPT ads felt quite frequent. About one out of every five questions in a new conversation thread triggered an ad at the bottom of the chatbot’s output. These ads always included a website link as a button and were tailored to the general topic of my question. As OpenAI continues to experiment with ads in ChatGPT, the formatting and the frequency of these ads may change.

“Because ChatGPT is a trusted and personal environment for many people, we’re intentionally rolling ads out slowly,” an OpenAI spokesperson tells WIRED. “Starting with a limited number of advertisers and formats while we iterate based on what we learn.” OpenAI claims the decision to roll out ads now is not tied to any rumored IPO later this year, but rather part of a long-term strategy to keep ChatGPT broadly accessible.

The ChatGPT ads felt recurrent in my early experiences, but the range of topics covered was extensive and always tailored to my most recent prompt. I saw an ad for Uber that read “Your Schedule, Your Earnings” when I asked about the gig economy. OpenAI gave me an ad for Page Six’s Hollywood newsletter below the answer when I asked about the worst TV show ever. (The bot floated The Jerry Springer Show and Cop Rock as two possibilities.) My question about Harvard versus Stanford triggered an ad for the University of Minnesota’s part-time MBA program.

Overall, I saw ads for dog food, printers, hotel reservations, productivity software, movie tickets, food delivery apps, fashionable ties, streaming services, corporate credit cards, apartment furniture, cruise vacations, AI coding tools, freelance editors, skin-care articles, business internet plans, handmade gifts, grocery stores, and basketball tickets, among others.

Questions related to travel currently seem to trigger ads the most often. When I asked for help planning a trip to Palm Springs, the ad attached to the bottom of the answer was for Booking.com. When I clicked on the link, it automatically searched for hotel deals in Palm Springs.

Before this year’s embrace of ads for free users, OpenAI CEO Sam Altman had expressed his distaste for chatbots with ads. “I hate ads,” Altman said during an onstage discussion at Harvard Business School in 2024. He said the mixture of “ads plus AI is sort of uniquely unsettling,” and it raised questions about who may be influencing a chatbot’s answers.

“I kind of think of ads as like a last resort for us for a business model,” he said. “I would do it if it meant that was the only way to get everybody in the world access to great services. But, if we can find something that doesn’t do that, I’d prefer that.” I guess 2026 is the year for some last-resort moves. OpenAI recently discontinued Sora, its social media app for AI videos, and scrapped plans for an erotic version of ChatGPT. Leaders at the company are attempting to streamline operations and stave off the competition by increasingly focusing on core products.

OpenAI started testing ads in ChatGPT in February in the US. I first started noticing them in my tester account in early March. The company claims that ads do not impact the content of ChatGPT answers and that your full conversation is not shared with companies paying for ad placements. The ads that are served to users are influenced by the topic of your question as well as your past chats and whatever ChatGPT stores in its memory about you.

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