This holiday season, shoppers have more artificial intelligence to help with their gift lists.
Target, Walmart, Ralph Lauren and other retailers this year unveiled chatbots that act as conversational stylists and shopping assistants. That means people who want to find matching pajamas for the family can ask a chatbot to sort through the options, or for a summary of customer reviews of an air fryer.
At the same time, A.I. companies are getting into e-commerce. In September, OpenAI debuted an instant checkout feature in ChatGPT so people can buy items from stores such as Etsy without leaving the chat. This month, Google announced an A.I. assistant that can call local stores to check if an item is in stock, while Amazon rolled out an A.I. feature that tracks price drops and automatically buys an item if it falls within someone’s budget.
The goal is to provide shoppers with a tailored and convenient experience, retailers and tech companies said. Many of the new chatbots are “agents,” which are programs that act autonomously and can respond to specific questions and context. They go beyond customer service chatbots that could handle only limited questions about returns or the status of an order.
The latest chatbots can make holiday shopping more “personalized, efficient and cost-effective,” said Lori Schafer, the chief executive of Digital Wave Technology, which helps companies with A.I. tools.
“It fundamentally changes how people shop — moving from humans searching for products to A.I. bringing the right products, at the best price, directly to them,” she said.
The A.I. tools can also help people deal with “decision fatigue from endless options,” said Luca Cian, a marketing professor at the University of Virginia’s Darden School of Business. Consumers are turning to chatbots to compare prices and save time so they can feel more confident in their decisions, he added.
“The transformation ahead isn’t just technological; it’s psychological,” Dr. Cian said. “We’re recalibrating our relationship with choice itself, learning when to delegate decisions and when to maintain control.”
Roughly 42 percent of shoppers are already using A.I. tools for their holiday shopping, according to a survey of more than 4,000 consumers that Harris Poll conducted for Mastercard last month. More than half of Generation Z and millennial respondents said they trusted A.I. to recommend unique gifts.
But many of the A.I. tools are still experimental and unproven. Some consumers said the chatbots failed to provide enough brands or types of products in their conversations.
Olivia Meyer, 24, who works in the fashion industry in New York City, used ChatGPT this month to search for a pair of winter boots and was frustrated when it kept showing her the same brands.
“I haven’t been as completely satisfied with what I found, and so then I just end up going back to Google search or TikTok to try and find what I’m looking for,” Ms. Meyer said.
Consumer expectations about A.I. shopping may be ahead of reality, said Tyler Murray, the chief enterprise solutions officer of commerce and technology at VML, a marketing agency. True autonomous shopping, “where A.I. agents truly understand you, find the perfect gift and orchestrate the entire purchase journey, isn’t quite here yet for this holiday season,” he said.
Retailers are rolling out upgraded chatbots and A.I. features in the meantime. This month, Target introduced a free chatbot that offers to find gifts by having a conversation with a user about the age of the person the shopper is buying for, the recipient’s interests, the occasion and the shopper’s budget. It is a more advanced version of Target’s A.I. “gift finder” from last year, which did not allow for free-flowing conversations.
OpenAI also beefed up ChatGPT’s shopping features this year. In April, the company added images and links to product results in ChatGPT. In September, it rolled out the instant checkout feature with Etsy so ChatGPT users in the United States can hit a “buy” button on certain products without leaving the conversation. Shopify merchants such as Skims, Spanx and Glossier also recently became available for instant checkout. OpenAI takes a cut of each sale, but declined to disclose how much.
This week, OpenAI said it had begun rolling out a shopping research feature in ChatGPT that offers users more refined product results than a typical chat does.
OpenAI is working to expand the products that show up in ChatGPT’s instant checkout, said Michelle Fradin, the ChatGPT commerce product lead, adding that A.I. shopping is still in its “early” stages. The company has announced a partnership with Walmart, though its products are not yet available through the checkout feature.
(The New York Times has sued OpenAI and Microsoft, claiming copyright infringement of news content related to A.I. systems. The two companies have denied the suit’s claims.)
Among those won over by A.I. shopping is James Wilsterman, 38, a San Francisco tech executive. This summer, he used ChatGPT to shop for blazers and linen shirts for a wedding in France. He does not like to go shopping, so ChatGPT’s carousel of images and direct links helped him find new brands, he said.
Mr. Wilsterman said he planned to keep using A.I. to check off items on his holiday shopping list. “What has changed for me is that this is less intimidating,” he said.
There’s another bonus, too. If his family does not like the gifts, he said, “I’ll blame it on ChatGPT.”
Natallie Rocha is a San Francisco-based technology reporter and a member of the 2025-26 Times Fellowship class, a program for early-career journalists.
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