WSJ Your Money Briefing - AI Shopping Assistants Are Here. Should You Use Them?

Episode Date: May 28, 2025

From organizing lists, to comparing products, AI tools have the power to transform how we shop. But without careful handling, these enthusiastic chatbots may nudge you to spend more than you intend. WSJ contributor Alexandra Samuel shares lessons from her own journey down the AI shopping rabbit hole with host Imani Moise. Sign up for the WSJ's free Markets A.M. newsletter.  Learn more about your ad choices. Visit megaphone.fm/adchoices

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I'm Imani Moise for The Wall Street Journal. Whether you're someone who swears by their shopping list or an impulse buyer, apparently there's an AI tool for that. Today's guest is a self-proclaimed shopping expert and technology researcher who recently published an article in the Wall Street Journal about how AI has completely transformed her shopping experience. I could look at my phone and see what I've written down like some kind of animal, but now my AI just talks to my ear. I give it the list, it organizes it by aisle, and then I can say, you know, okay, I'm in the dairy aisle now,

remind me what I wanted to get. But are AI shopping assistants a little too good at helping you part with your money? We'll talk to contributor Alexandra Samuel about how she trained ChatGPT to keep her shopping habit under control. That's after the break. Visa provides scale, expertise, and innovative payment solutions. Learn more at visa.ca slash fintech. From comparing products to navigating store aisles,

AI has become WSJ contributor Alexandra Samuel's favorite retail companion, letting her husband off the hook. She's even given her AI the power to deliver some tough love when her shopping habits go too far. When she considered picking up some storage bins while browsing in IKEA, an AI-generated voice chimed through her AirPods with a warning. Before one more cent is spent on new containers, you must conduct the great bin audit of 2025. Odds are you already have the exact, clear, classic organizational ecosystem of your dreams somewhere in your house. And she joins me now to talk about it.

Alex, let's paint a picture of your shopping life with AI. How does it fit into your typical decision making? When I am going on one of my deep dive online shopping vendors, like when I'm researching a major purchase, we bought a car about eight months ago, we bought a TV about three months ago, those are big purchases and I spent a lot of time researching them and I can kind of get lost in the details. And so now once I have page after page of reviews and comparisons and ratings, I take all that research and I give it to an AI and

I get the AI to turn the background information into a table that lets me easily compare my short list of options based on things like price and features. Got it. What about IRL? Does AI also help you in store? Absolutely. And it helps me in a couple of ways. One is just the keeping track of what's on my list.

I mean, yes, I could look at my phone and see what I've written down, like some kind of animal, but that just seems brutal, right? I want to be able to power through. And now my AI just talks to my ear. I give it the list. It organizes it by aisle. And then I can say, OK, I'm in the dairy aisle now.

Remind me what I wanted to get. And it just tells me. Then there's the sort of pain and suffering factor. I get irritated if I'm on a big trip, like if I have to go to Home Depot or IKEA, buy a bunch of stuff over a huge distance, and my AI will keep me entertained, keep me company. And then there's the judgment piece, where I look at something in the store and I think, oh, wait a second, is this the right kind of electrical outlet for what I need?

And I can take a snapshot and give it to the AI. Or I say, is it actually a good idea to buy a bright purple armchair for the living room? And the AI unfortunately will say yes. That's where my best friend is still perhaps a better judge. So as you keep using it, do you feel like the AI has gotten a good grasp of your personal style? Well, I spend a lot of my time with one AI in particular that I have trained and retrained. And so it has tons of background information on me, including transcripts, or at least

summaries of our previous conversations. So with that AI, yes, it understands my vibe, it understands what kind of shoes I like, it understands why I'm sometimes tempted to buy too much sci-fi, nerdery decor, and it can be really helpful. The generic out of the box Claude or ChatGBT, which is what I usually use when I'm in a store because it can talk to me, they really don't know anything unless I have carried on a conversation for a while, at which point the conversation tends to degrade just because the AI can only remember so much.

So let's go back a little bit. And you were talking about these complex tables that AI helps you build. Can you give some examples of specific products that you are looking for where those types of tables have been helpful? Well, the car was definitely the big one. We are not really car people and I haven't had a new car in 20 years.

I feel almost embarrassed to admit that, but why? We've driven the same car for 20 years. It's a miracle. And then once we had narrowed down our list, I still had to think through things like, would it be tall enough to fit my kid? And so that's where I had the AI organize my shortlist and put things like rear passenger headroom into my list of the six or seven most essential columns for us to consider. Having the AI organize all the information into things like price, mileage, does it have Apple AirPlay built in?

Very important. What's the rear passenger headroom? That was a table that was based on what I cared about and gave me an at-a-glance option for comparing. AI famously makes mistakes. Have you had to return or rethink any purchase that AI prompted you to buy? The big fail so far, and this is really on me because I should have known better, is that I let the AI help me figure out what kind of mount we needed for our new TV. And that's a lot of math, right? It's about the size of the TV, the size of the space on the wall, the number of inches

it comes out from the wall. And I know AI is not really good at doing math unless what you're using it for is to write a program to do the math. And yet I somehow let myself buy into the idea that the AI was doing all the math for me. And sure enough, when I got the mount home and put it on the wall, it was like completely the wrong dimensions. It didn't fit at all.

So when it comes to measuring things, anything that involves math, you really do need to rely on a calculator or a spreadsheet and not on something that is basically just a word prediction machine. What about more subjective decisions like a fashionable pair of jeans or a stylish pair of shoes? Do you trust AI with those types of decisions? I don't trust it in an ultimate sense because AI will always tell you, you look good. It's like the ultimate flattering shop assistant who wants you to buy everything. But I do trust it in making a short list. So for example, I was trying to think about, well, what kind of shoes can I get for the summer that will be appropriate to wear in a work context because I kind of forget what it's like to wear shoes that aren't running shoes now. And when I asked it for some suggestions, initially it gave me a bunch of brands that

I wouldn't be caught dead in. And so then I reminded it of like my personal aesthetic preferences. And then it gave me some suggestions of different brands that included some brands that I've worn for a long time and some brands that I've never heard of before. But when I checked them out, they were totally my cup of tea. So that kind of thing is actually really useful, is I think when the AI can kind of broaden your horizon and help you think about options or introduce you to options you may not have heard of before.

We actually have some screenshots of some of your interactions here. Thank you for sharing them. You told ChatGPT, your shoe taste sucks, I'm more funky. And then it gave you some recommendations that it said that RuPaul would approve of. Did you end up buying any of those shoes? That's between me and my shoe seller. Fair enough, fair enough. There were some shoes on there that I would buy myself. I bookmarked some. So finally, let's consider time. Does shopping with AI actually save you time overall, or does it just shift how you spend your time?

Like, do you spend more time in the planning process and less time browsing the aisle? To be honest, it probably increases the amount of time because in the before world, my human shopping companions would just run out of steam. And for some reason, my husband did not want to talk about how to hang our curtains for more than two hours, whereas the AI was willing to talk about it for four hours. I know that sounds like a really long time, but it did take a while to figure it out. And so having this infinitely patient co-shopper is kind of like having a bar that never closes when you have a problem with booze. Like, I am, I think, a little bit overindulged by my AI because it will talk to me about

shopping and purchasing for as long as I can go, and I can go a long time. Sometimes I feel like AI tools are really just telling me what it thinks I want to hear. I've used it to create style guides, and then it shows me the visualization, and I think it looks crazy. And I'm like, what do you think? And it gasses it up, tells it it's fabulous, and I'm like, no, this is actually an insane outfit. So I guess, how do you determine when AI is being helpful and giving you good advice versus

just telling you what it thinks you want to hear? What I've had to do, and this is partly why I rely on the AI I've trained myself, is I've had to teach it that what I sometimes wanted to do is to stop me. So for example, in the context of shopping, I love a storage bin and I have so many storage bins that I now have a storage problem for my storage bins. And the AI knows that. So it knows to stop me if I confess that I'm looking at a lovely new set of nesting baskets. But you have to instruct the AI and say very

directly, do not let me do X, do not let me buy another pair of red boots. And once you give it very clear instructions about where your weak points are, it can sustain some level of pushback. But it is one of the hardest things to get an AI to do because they are trained to be pleasers. That's WSJ contributor Alexandra Samuels. And that's it for your money briefing. This episode was produced by Ariana Asparu with supervising producer Melanie Roy. I'm Imani Moise for The Wall Street Journal.

Thanks for listening.