At its very best, gift-giving is a a small act of surveillance that feels like a whole lot of love. So every December, I become Santa Shannon: part private investigator, part curator with a slight Pinterest addiction and definitely too many open tabs. I have a running Notes app list of gift ideas; I’ve collected offhand comments, fleeting obsessions, and “This would look perfect in my home” texts starting way back in March — because feels quite as good as watching someone unwrap proof you were paying attention.
Being Santa Shannon is very fun. Being Santa Shannon is also very tiring.
I’ve written a lot about AI shopping tools this year, and I remain a skeptic — both on aesthetic grounds and because I don’t love the idea of strip-mining the Amazon rainforest to buy my mom another tote bag. But for the sake of a good story, I decided to try the tech everyone insists is the future. What did I find? An algorithm deeply convinced my dad wants socks and that finds my mom just as hard to shop for as I do — only with more confidence and worse judgment.
I told ChatGPT my strategy: Thoughtful. Preemptive. Unique. No Target or Amazon unless absolutely necessary. I told it about my sister, Clare, an immigration attorney in Washington, who rock climbs, bakes, reads constantly, steals from my closet — like any good little sister — loves her Chelsea boots, and hikes a bunch with her one-year-old dog, Red. I told it about my mom, a former PR pro with a full kitchen and even fuller taste, who loves French-inspired cooking and gardening, and who misses Lake Tahoe daily — she and my dad recently moved, and she lost a lot of things in the process. I told it about my dad, an author and former business journalist who just reorganized his bookshelves to make them the star of his house, loves Civil War history and Russian literature, does the New York Times crossword as soon as it’s posted, and is woefully underprepared for a humid East Coast summer.
I limited my showers all week to five minutes to atone for the environmental cost.
ChatGPT “listened” to my detailed portrait of my family and did what it does best: It summarized them into a set of neat, purchasable archetypes. My sister became a “tasteful, athletic, high-functioning adult with opinions.” I read that out loud to her. “High-functioning?” she said. “Whoa. I’ll take it.” My mom emerged as “high taste, low tolerance for stuff, emotionally anchored to place.” My dad landed as “brilliant, opinionated, under-invested in clothes, ready for upgrades.” And then the model started recommending gifts for the version of my family that exists in the space between “stereotypical gift guide” and “found in an airport bookstore.”
For Clare, ChatGPT proposed the kind of cookie-cutter sister gift ideas that, as it so happened, included cookie cutters (for office bake-offs). ChatGPT suggested a “genuinely good claw clip or hair accessory,” and got specific about materials, because nothing says intimacy like acetate or tortoiseshell. But Clare bakes brownies and cakes, rarely cookies — and she never uses one of the 100 cookie cutters I keep in our shared kitchen. I’ve never seen Clare once use a claw clip; she usually has at least one scrunchie on her wrist. ChatGPT’s gift ideas relied on a phantom version of my sister and then built from there.
The thing about AI “personalization” is that, half the time, it’s not personal. ChatGPT’s ideas were fine. They’re what you’d buy if you were shopping for a person-shaped prompt. The AI doesn’t know that my mom is especially picky, and it can’t help me when she is. AI can’t offer a suggestion that carries the history embedded in my family’s daily texts.
I expected ChatGPT to struggle with ideas for my mom, and it did. Saying she’s the hardest person I know to shop for is an understatement. She has impeccable (and highly specific) taste. She doesn’t like random clutter. She’s been collecting items for more than 60 years, which means ChatGPT’s “She’ll love this” is a bold claim.
The model heard “French-inspired cooking and gardening” and started tossing Provence-coded items at me. So: a French utensil holder; French gardening tools; a French lavender bath soak; a classic French-style picnic basket. Each suggestion had AI’s cheerful logic, and I could feel myself getting more annoyed as ChatGPT and I chatted. I tried to tell ChatGPT about my mom. No, my mom doesn’t really take baths. No, my mom already has gardening shears. No, my mom doesn’t want a tacky Lake Tahoe souvenir disguised as décor.
So then it suggested: “A premium smart skipping rope (counter + metrics).”
I laughed. What else is there to do when an AI chatbot recommends high-impact cardio for a woman over 60 who has had two knee surgeries. I told my dad. He responded:
“Is ChatGPT trying to kill your mother?”
There are a lot of ways to be wrong in gift-giving — wrong because you didn’t listen, wrong because you bought something you wanted them to have, etc.. The skipping rope was a bright, chirpy example of what happens when a system doesn’t know the difference between “fitness” as a category and “fitness” as a someone’s reality.
My dad’s section was a different flavor of wrong. The model heard “author” and started handing me props: a pencil set, a notebook, a desk accessory, a fountain pen. Then the model settled on me giving my dad a pair socks. I told ChatGPT that I didn’t really want to give my dad socks this year, so it responded by doubling down with a more earnest version. Not socks, it insisted. PERFORMANCE socks. Unfortunately, I told the model, I was looking for a present that says something closer to: “Thanks for helping me make sense of my word vomit when I text you frantically on deadline.”
That’s when I realized what I kept bumping into: The model wasn’t trying to know my family; it was trying to complete a task.
Luckily, as it turned out, I didn’t actually need the AI’s help. By the time I was feeding ChatGPT this rich dossier and watching it spit back a list of plausible objects with the confidence of a horoscope, I wasn’t actually shopping for anything.
Clare’s gift was already sitting in my cart before I opened the chatbot: a jewelry box. She loves to buy rings when we travel together, and they sit scattered across her room like a tiny, sparkly landmine field. My sister and I had already picked out the big things for my parents — a first-edition set of Ulysses S. Grant’s memoirs for my dad and replacements for the things my mom lost in her move: a Jimmy Choo purse from The RealReal and a gorgeous KitchenAid stand mixer that’s something close to burgundy — how very French of me after all. (I made them all promise not to read this story until after Christmas, so this will be our little secret, OK?)
ChatGPT eventually found its way toward those lanes. After I steered the model in the right direction, it mentioned getting my dad a beautiful edition of a beloved author, and it talked about honoring the “books as identity moment” my dad was in, whatever that means. ChatGPT mentioned replacing what my mom lost with upgraded versions — but it felt like the model was narrating back the conclusions I’d already reached. I kept having the same suspicion that I’d led the horse to the trough, then watched it take a drink and tell me it had discovered the water.
I tried Google’s Gemini and Claude’s Anthropic, too. AI can be useful as a search tool, and Gemini was better at that kind of usefulness when I tested it. Claude asked a dozen follow-ups, which felt closer to how a good salesperson would behave. Gemini’s tone was smoother and more helpful in a gift-guide way. But none of the models did the thing I actually needed, which was to know them and understand them — in real life.
Clare is a rock-climbing lawyer, sure. She’s also a former cross-country champ, a Yale graduate, and the person who loves to share a bottle of wine with me on the couch, halfway listening to whatever sport we’ve put on TV. My mom has the highest level of taste of anyone I know — unless our tastes clash, in which case I’m right. My dad is a big-hearted genius and has read more Russian literature than is probably healthy. ChatGPT kept trying to get me to buy objects that would make sense for the people in its summary, not the people I know and love.
So no, Santa Shannon doesn’t want to outsource her job. She wants fewer tabs, sure, but she doesn’t want a machine to flatten her family into patterns and call it thoughtfulness. The personalized giving is the fun part for me. It’s my family. I know too much about them — and I still want to prove it, one December at a time.
This article first appeared here.
