A.I. Is Quietly Taking Over Your Holiday Shopping
New artificial intelligence tools from big-box stores and tech giants are stepping into the role of gift concierge this holiday season, helping people pick presents and manage their shopping lists.
Target, Walmart, Ralph Lauren and other retailers have rolled out chatbots that act like virtual stylists and shopping assistants. Instead of manually scrolling through pages of products, a shopper can now ask a bot to find matching family pajamas or summarize reviews for a popular air fryer and get tailored suggestions in seconds.
At the same time, A.I. platforms themselves are moving deeper into e-commerce. In September, OpenAI added an instant checkout option inside ChatGPT, allowing people to purchase items from marketplaces like Etsy without leaving the conversation. Google recently introduced an assistant that can call nearby stores to confirm if a product is available, and Amazon unveiled an A.I.-powered tool that monitors price drops and automatically buys an item once it falls within a user’s chosen budget.
The overarching promise, according to retailers and tech companies, is a more convenient and customized shopping experience. Many of these systems are what the industry calls “agents” — software programs that can act on their own, understand context and respond to specific needs, rather than just answering basic questions about returns or tracking numbers.
Lori Schafer, chief executive of Digital Wave Technology, which builds A.I. solutions for brands, said these tools can make holiday shopping more personalized, efficient and affordable. In her view, the shift is from people hunting for products themselves to A.I. surfacing the right options — at competitive prices — directly to them.
Easing the Overload of Endless Choices
Beyond convenience, some experts argue that A.I. can address the stress that comes from having too many options.
Luca Cian, a marketing professor at the University of Virginia’s Darden School of Business, said shoppers are increasingly turning to these tools to compare prices and narrow choices so they feel better about their final decisions. The bigger change, he suggested, isn’t only about technology; it’s about how people approach choice. Consumers are learning when they’re comfortable letting algorithms decide for them and when they want to keep control.
A recent survey by Harris Poll for Mastercard, which included more than 4,000 consumers, found that about 42 percent are already using some form of A.I. for holiday shopping. More than half of Gen Z and millennial respondents said they trust A.I. to find distinctive or unusual gifts.
Promise vs. Reality
Still, the current generation of A.I. shopping tools is far from perfect. Many of the systems are experimental, and some users say the experience feels limited or repetitive.
Olivia Meyer, 24, who works in fashion in New York City, recently tried ChatGPT to look for winter boots. She said the recommendations leaned too heavily on the same brands and styles. In the end, she reverted to more familiar tools like Google Search and TikTok to continue her hunt.
Tyler Murray, chief enterprise solutions officer for commerce and technology at the marketing firm VML, said consumer expectations may be a step ahead of the technology. He noted that a truly autonomous shopping experience — where an A.I. agent fully understands your tastes, finds the right gift and manages the entire purchase flow — isn’t quite here yet for this holiday season.
How Retailers Are Upgrading Their A.I. Helpers
In the meantime, retailers are steadily enhancing their digital assistants.
This month, Target launched a free chatbot designed specifically for gifting. It asks shoppers about the recipient’s age, interests, the occasion and budget, then suggests products accordingly. It builds on last year’s simpler “gift finder,” but now allows more natural back-and-forth conversations.
OpenAI has also expanded ChatGPT’s shopping capabilities. In April, the company began including product images and links in responses. In September, it introduced instant checkout with Etsy so users in the United States can tap a “buy” button on eligible items without leaving the chat. Shopify brands such as Skims, Spanx and Glossier have recently become available through the same flow. OpenAI earns a percentage of each sale, though it has not publicly disclosed the amount.
This week, the company said it had started rolling out a “shopping research” experience within ChatGPT that aims to provide more focused and refined product recommendations than a standard conversation.
Michelle Fradin, who leads commerce for ChatGPT, said the company is working to expand the range of products available through instant checkout and emphasized that A.I. shopping is still in its early days. OpenAI has announced a partnership with Walmart, though Walmart’s items are not yet integrated into the checkout feature.
Winning Over Skeptical Shoppers
Some consumers are already sold on using A.I. as a shopping partner.
James Wilsterman, 38, a tech executive in San Francisco, turned to ChatGPT this summer to put together outfits — blazers and linen shirts — for a wedding in France. He said he dislikes traditional shopping, and found it helpful to see a carousel of looks with direct links to buy, which also introduced him to brands he hadn’t tried before.
Wilsterman plans to keep using A.I. tools to tackle his holiday gift list, describing the process as less daunting than wandering through stores or clicking through endless pages of results. And if his family doesn’t love what he picks out?
He joked that he has a built-in excuse: he’ll simply say it was ChatGPT’s idea.
Leave a Comments