November 14

Holiday Shopping with AI

Can you believe we are halfway through November? For many of us, it’s time to get into gift-giving mode, and AI is going to make it easier. Or not.

Not surprisingly, AI chatbots are getting into the gift-recommendation space, and some will even shop for the best prices for you. Plus, if you trust AI enough to give it access to your credit cards, you can even purchase through some platforms.

But there are a lot of “buts” here. I tried out a bunch of gift-recommendation tools to find the good sides and bad with the following prompt: “The five-year-old daughter of my manager. She likes Legos and girly stuff. Under $25 budget.”

AI Shopping Tools

Major Retailers

Your major retail stores really, really want you to use their new internal tools for shopping.

Walmart’s Sparky

Walmart’s new AI chatbot, Sparky (insert eyeroll for name here), is only available via smartphones, which annoyed me because I didn’t want to download yet another app. But it followed my prompt and gave me lots of options in my budget. Plus I like that it saved my chat history and offered to help me refine my request.

Another potentially fun feature: Sparky says it helps you with party planning. But I told it to plan a Cookie Exchange Party and all it did was give me a whole bunch of things to buy like sugar, a tablecloth and trashbags. I was hoping for a conversation or at least a few more questions to clarify.

Amazon’s Rufus

Aww. You gotta love an AI tool that was named in honor of a dearly loved corgi. Amazon launched Rufus almost two years ago, and it has gotten much better. You can use it on the app and online, which beats Walmart for sure.

But Walmart wins when it comes to saving the chat history. Like Walmart, Rufus handled the request for a young girl’s gift ideas in a snap, even picking a bunch of options well under the $25 budget.

Screenshot of an online shopping page for LEGO Friends & Princess Sets, perfect for Holiday Shopping, featuring dog grooming and unicorn & flamingo-themed building toys for children, with prices, ratings, and delivery details shown.
Screenshot of an Amazon product page for LEGO Classic Magical Transparent Box, perfect for Holiday Shopping, showing price, rating, delivery info, and a brief product description about building transparent, sparkly creations.

Just for fun, I asked Rufus to plan a party as well. It did a MUCH better job. Now I really want to have one.

A mobile screen displays AI-powered search results for party invitations and recipe cards, featuring cookie exchange invitation options, prices, holiday shopping delivery details, and "Add to cart" buttons.
Amazon search results for Christmas party favors make holiday shopping easy, with Christmas cookie quiz game cards and Christmas fortune cookies, all showing prices, ratings, Prime eligibility, and "Add to Cart" buttons.
Screenshot of a list of planning tips for a cookie exchange, including invitation, recipe sharing, cookie quantities, packaging, and activities—plus related search suggestions for Holiday Shopping with AI at the bottom.

Target’s Gift Finder

Target just released its Gift Finder, which doesn’t have a cutesy name but does have a cutesy mouse avatar. It gave me plenty of gift ideas, most of which were just barely under my budget. A couple of interesting quirks: The mouse said, “Please note–I am showing you the best matches from the information we currently support.” Not sure what that means.

I also found it puzzling that I had to push a button to go to the product recommendations, where the other tools listed offerings in the chat. Like Amazon, it didn’t look like I could see my chat history, but I could ask follow-up questions.

When I asked it about the cookie exchange party, it asked my budget, which was helpful. But then it recommended really pricey serving bowls, and this monstrosity. Who the heck would want that as cookie exchange party decor?

A black stoneware bowl with round orbs attached around the rim, perfect for Holiday Shopping, is priced between $26.99 and $35.99 and sits above "Add to cart" and "Wish list" buttons.

Chatbots

Of course the big AI chatbot tools want in on the affiliate income of online purchases. Every time you click and buy, they get paid.

Perplexity

I wrote about Perplexity’s AI shopping a while ago, and it has improved since then. They actually have a specific Shopping option in the sidebar. It did a great job of recommending toys. It also added a button where I can click to buy directly from the browser rather than having to go to the retail site. That feature is only available to Pro users.

Screenshot of a webpage suggesting LEGO gift ideas for a five-year-old girl, including Gabby's Dollhouse and a Magical Unicorn LEGO set—both under $25—to simplify your holiday shopping.
Screenshot of a webpage listing classic craft and play alternatives for children, featuring Hasbro Play-Doh and Kinetic Sand playsets—perfect inspiration for holiday shopping—with brief descriptions, images, and even a touch of AI-driven recommendations.

Trying to plan a Cookie Exchange Party with the Shopping tool was a bust, although it gave me lots of cool tips. Every once in a while, these AI tools will provide two answers and ask you to pick the best one. It’s part of the AI training and another reminder that we’re all in one big beta test. After the Perplexity fails, I abandoned the Cookie Exchange Party exercise with the other two platforms.

Screenshot of a comparison between two AI-generated answers about planning a cookie exchange party for 14 guests, complete with voting options to decide which AI provided the best ideas for your holiday shopping and celebration needs.

Google Gemini Shopping

Again, no fun name here, but as of yesterday Google’s AI Mode now includes shopping assistance. I like that you can click a box next to the products to ask follow-up questions, and clicking on a product will give you options for where to buy and price tracking.

Bonus (maybe): You may be able to get Google to grab a great deal for you automatically if you’re tracking prices and have access to the platform’s agentic checkout.

Screenshot of a Google search results page showcasing LEGO gift options for kids—perfect for Holiday Shopping—with product images, prices, and retailer links for sets like the LEGO Friends Pool Party and Dog Grooming Car.

ChatGPT

ChatGPT just started jumping into the instant shopping world, and it’s pretty limited. I got paragraph after paragraph of advice, but the products it pulled up lacked real-time info.

Three LEGO sets for kids: a unicorn model, a colorful café, and a horse and pony trailer—each boxed with vibrant artwork and age recommendations. Perfect for holiday shopping or gifting to inspire creativity.

Tags

shopping, utility


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  • Thanks a ton for doing this for all of us. I hadn’t thought about using AI for gift shopping but now I will. I so appreciate not having to be a guinea pig myself. Thank you thank you. Nerd on!🤓

  • Wish that the AI tools led to finding the perfect gift from local craftspeople. Or at least tied into Etsy. Target, Walmart and the like don’t need any more help with their retail sales, while talented artisans in every town in America rely on this season for most of their yearly sales. Perhaps a guide to local art festivals and craft fairs with links to the vendors would be more helpful than another way to purchase “the best Legos kit” for someone on your list. A hand crafted gift is more meaningful and boosts the local economy because that local craftsperson you purchase from is likely to spend that money locally, too.

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