My Not-So-Perfect Holiday Shopping Excursion With A.I. Chatbots

To help with my holiday shopping this year, I recently turned to a new personal assistant online. “I’m looking for a Christmas present for my mother, who spends long hours working,” I typed. “Is there something she can use in her office every day?”

“Of course!” came the instant reply. “Does your mother have any specific preferences or needs for her office? For example, does she need organization tools, desk accessories, or something to help her relax during breaks?”

So began my conversation with Shop A.I., a new chatbot from Shopify, an e-commerce marketplace. Over 10 minutes, Shop A.I. and I engaged in a question-and-answer session. I told the chatbot my budget and more about my mother, such as her need to alleviate back pain. Shop A.I. also asked me about my mother’s preferred design and color for an office chair.

More people may eventually replicate this kind of shopping experience. A year after ChatGPT debuted, retailers around the world have started rolling out chatbots that are powered by generative artificial intelligence. That makes this holiday season the first when a slew of A.I. chatbots can help shoppers brainstorm and find presents for their friends and loved ones.

In addition to Shopify, chatbots have come out over the past 12 months from Instacart, the delivery company; Mercari, a resale platform; Carrefour, a retailer; and Kering, which owns Gucci and Balenciaga. Walmart, Mastercard and Signet Jewelers are also testing chatbots, which may become publicly available as soon as next year.

“In a way, it’s recreating an in-store environment, but online,” said Carl Rivera, a vice president at Shopify who oversees its Shop app, which hosts Shop A.I. He said the chatbot broke down people’s questions into key terms and searched relevant products from Shopify’s millions of sellers. It then recommends products based on reviews and a shopper’s purchase history.

Retailers have long used chatbots, but previous versions lacked conversational power and typically answered just a few preset questions, such as the status of an order. The newest chatbots, by contrast, can process prompts and generate tailored answers, both of which create a more “personalized and authentic interaction,” said Jen Jones, the chief marketing officer of the platform Commercetools.

Whether shoppers want this technology remains a question. “Consumers like simplicity, so they don’t necessarily want to have five different generative A.I. tools that they would use for different purposes,” said Olivier Toubia, a marketing professor at Columbia Business School.

Nicola Conway, a lawyer in London, tried Kering’s luxury personal shopper, Madeline, in August to search for a pink bridesmaid dress for a spring wedding. Madeline was “intuitive and novel,” she said, but it gave only one recommendation, an Alexander McQueen corset dress. Ms. Conway did not end up buying it.

Kering did not respond to requests for comment.

Maggie Weber, a shopping influencer who uses the social media handle @refashionedhippie, said she tried Mercari’s chatbot, Merchat A.I., in May. She asked the chatbot to show her baseball cards, but she was instead offered baseballs — and then hats, bats and jerseys.

“Merchat is still in its infancy,” Ms. Weber, 34, said. She added that she worried that if she gave the chatbot too much information, it would start directing personalized ads to her.

A Mercari spokeswoman said Merchat used chat history only to recommend products and did not use personally identifiable information. She added that the search bar could be faster for customers who want a specific item, while the chatbot helped those who want “inspiration for gifts.”

Such inspiration was exactly what I needed this season as I had only vague ideas for what to buy my 53-year-old mother and my 17-year-old cousin, Jenny.

So I tried Shop A.I. After telling the chatbot about my mother’s back pain and asking what I could buy to help her relax, Shop A.I. offered to find an ergonomic chair and asked my budget. When I said $100, it came back with a few pages of product results.

“Can you help me to narrow it down?” I typed. Shop A.I. then asked about my preferred color for a chair. I said black.

Shop A.I. returned more than 300 results, including a $159 camp chair from ROAM Adventure, a $179.99 reclining massage office chair from homrest and a $269.99 CosyGaming executive chair.

“These don’t seem to be under $100,” I wrote, annoyed.

“As a new chatbot, I’m still learning and sometimes the search results may not be accurate,” Shop A.I. replied. “Let me try again and find some black ergonomic chairs within your budget.”

Then, it added, “It seems that I’m having trouble finding black ergonomic chairs within your budget at the moment.”

I ended up typing “black ergonomic chair” into the search bar myself and set a $100 price range. A $66.81 Victory Furniture gaming chair and a $47.96 massage office chair popped up, though they were too big and heavy to be gifts.

Eventually, I asked Shop A.I. for alternative ideas and received five options, including seat cushions and standing desk converters.

I chose the standing desk converter and gave Shop A.I. my $100 budget. This time, the chatbot showed options within my price range, including a $99 Risedesk standing desk converter. But most of the products did not have reviews, which I rely on while shopping online. I didn’t buy anything.

Shop A.I. was not great at finding a gift for my cousin, either. I wanted to buy Jenny some college dorm decorations featuring her favorite anime series, Violet Evergarden, which follows a character named Violet as she recovers from an unidentified war.

But Shop A.I. appeared to decide that anything the color violet was connected to my query. It showed me wall art of purple mountains and posters of purple BMW cars.

So I turned to Mercari’s Merchat. After asking for my cousin’s hobby (anime), age (17) and what she might prefer for college (dorm decorations), Merchat offered three gift ideas: wall tapestries, string lights and desk accessories in the theme of Violet Evergarden.

Merchat showed me four products under each category, all of which were under my budget of $50. I ended up buying a $18 Violet Evergarden poster scroll for Jenny. (She later told me she wished I had gotten her something quirkier.)

Emboldened by the experience, I asked Merchat to help find a present for my mother. “Would she benefit from a back support cushion, a heating pad or maybe a massage chair pad?” it asked.

“What are the pros and cons of each?” I typed.

Merchat said it couldn’t provide specific pros and cons for individual items. I changed my question to: “Which one is the easiest to use?”

This time, Merchat was definitive: the back support cushion, which was portable. Merchat detailed the differences between a memory-foam cushion and a firmer one, then further grouped memory-foam cushions into three categories and displayed the top four results for each, all under $100.

While I didn’t buy any because the styles were limited, it was a great starting point.

“Thank you,” I wrote.

“You’re welcome!” Merchat replied. “Happy shopping and have a wonderful time with your family!”