By Amanda Caswell

Getting everything on the list was easy with AI

(Image credit: Future/Gemini edit)

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When I was a kid, back-to-school shopping was my favorite. But as a mom with three kids and three different lists — kindergarten, fourth grade and sixth grade — going to the store to get everything is daunting. Plus, shopping with three kids in tow means there will be inevitable meltdowns over extras and nice-to-haves.

That's why this year, I decided to lean on three AI assistants to do the job for me. I gave ChatGPT, Gemini and Alexa+ the exact same school supply list and asked each one to shop for me. My instructions were simple: follow the teacher's list, stick to the required quantities, choose reasonably priced products and skip anything marked optional.

The results weren't even close.

(Image credit: Future)

ChatGPT was the most accurate

Once I uploaded the list, ChatGPT asked me to log into my Walmart account so it could do the shopping for me. I sat and watched as it took charge.

It followed the required brands and quantities, chose reasonably priced products and skipped every optional item exactly as I requested. Where the list allowed flexibility, it selected neutral colors instead of stopping to ask me to make decisions.

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The tradeoff was speed. ChatGPT took the longest to finish, but it spent that time checking the list carefully rather than rushing through it. The total came to $92.55 for my daughter's fourth grade school supplies. That seemed like a lot for just one kid.

Gemini was careful, but slightly more thoughtful

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(Image credit: Future)

(Image credit: Future)

After uploading the school supply list, Gemini created my cart through Instacart. Once I logged into the Instacart app, Gemini took control.

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Like ChatGPT, it avoided buying optional supplies. It also paused several times to ask me to approve colors for certain products instead of making the decision itself. This is something ChatGPT didn't do. I wasn't picky about colors, but it was a nice option as I know some kids are very particular. As a family that went through an entire year of "yellow" with my youngest, I get it.

That approach may appeal to shoppers who want more control, but it also meant the experience required more back-and-forth. ultimately bringing the total to about $60-$90. It would have been $105 with the optional water bottle.

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I was really surprised how low the price was, especially compared to Walmart. Gemini seemed to do a better job scanning the entire internet for the best deals from Instacart. Those unexpected results were interesting to see.

Alexa was lightning fast — but incredibly expensive

(Image credit: Future)

We are very much an Alexa+ family. I figured, why not use Alexa+ to shop for all our back-to-school needs. And while Alexa+ made the shopping experience a breeze, that convenience came with a hefty price tag.

Alexa built a cart totaling $251.48 — nearly three times what ChatGPT and Gemini found — and that was for just one kid! I'm going to have to get an extra side hustle at that rate.

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Unlike the other assistants, Alexa added everything it found, including optional items like headphones and a computer mouse that I had specifically asked it to skip. It also asked me to approve colors for several products instead of making those choices automatically.

If my goal had simply been to get everything into an Amazon cart as quickly as possible, Alexa succeeded. But if I had clicked "Buy Now" without checking the order, I would have spent well over $150 more than necessary. To be honest, I really wanted Alexa+ to win because shopping on Amazon is just so easy, but it was definitely a wake-up call.

Overall winner: Gemini

For this test, Gemini was the clear winner. It was more hands-on than ChatGPT and slower than Alexa, but the least expensive. It understood the assignment, followed the school supply list most closely, skipped optional purchases, but gave me the total with them in case I wanted to add them at the end. It also delivered the lowest total by a comfortable margin and was ready to deliver them.

The biggest takeaway was that AI shopping assistants are getting remarkably good, but they aren't interchangeable. The service they're connected to matters just as much as the AI itself. In this case, Gemini paired with Instacart proved to be the smartest — and cheapest — way to tackle my kids' back-to-school shopping.

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Amanda Caswell

AI Editor

Amanda Caswell is the AI Editor at Tom's Guide and one of today’s leading voices in AI and technology.

A celebrated contributor to various news outlets, her sharp insights and relatable storytelling have earned her a loyal readership. Amanda’s work has been recognized with prestigious honors, including outstanding contribution to media.

Known for her ability to bring clarity to even the most complex topics, Amanda seamlessly blends innovation and creativity, inspiring readers to embrace the power of AI and emerging technologies.

As a certified prompt engineer, she continues to push the boundaries of how humans and AI can work together.

Beyond her journalism career, Amanda is a long-distance runner and mom of three. She lives in New Jersey.