ChatGPT Shopping: Me vs the Machine
Can AI Choose Better Than I Can?
I had a special birthday present to buy for recently, and I couldn't help but see this was an excellent opportunity to test out ChatGPT's new shopping feature. Touted as being great for birthday presents and rushed anniversary gifts, I wanted to know if the combination of product recommendations and the ability to chat through and refine what might be suitable would result in some options that I would consider myself.
The best A/B tests are run when you have a good control group, and in this case, it was me. I had already pretty much made up my mind what I wanted to get. I normally pride myself on my ability to choose presents for those I care about, and I thought I'd done pretty well. But why not see if there was something I hadn't considered? Something even better? Would it even land on the exact same thing?
To start with I was envisaging running several versions of the test. I didn't know how my previous chats would influence the recommendations, so I was going to start with a blank slate, a vanilla account, then perhaps going to my own where it already knew my own history. But when I got started, I found the back and forth chat insightful and helpful enough that I changed my approach and stuck with the new account. I chatted for several pages, and the following is a rundown of what happened.
In my first prompt I introduced myself and my purpose. I spoke about what I was after: something thoughtful, small in size (for transport reasons), and intuitive. I gave a budget, and some brief details about the person I was buying for. I asked for something a little different, something that showed I knew this person well. But I wanted to frame the experiment correctly, as well:
I don't want to jump in with specifics of things they like. I'm happy for this to be a back-and-forth chat. But what sort of things might you need to know for us to get started? Right now, I'm looking for ideas, but you can help me find a specific item once I'm more certain what I want to get them.
In response, it came back with some aspects and details I could provide to paint a clearer picture:
Lifestyle & Daily Life
What does their day-to-day look like? (Commute? Work from home? Early riser or night owl?)
What do they tend to do when they unwind?
Creative, Intellectual, or Sentimental Leanings
Do they enjoy reading, writing, sketching, tinkering, games, puzzles, making playlists, journaling, etc.?
Any quiet hobbies or interests that seem to anchor them?
Their Aesthetic or Vibe
Are they minimalist or more eclectic?
Neutrals or colour? Modern tech or old-school analogue?
Things They're Drawn To
Any small clues from how they decorate, dress, or what they talk passionately about — even if only to you?
Shared Moments
Any significant little shared moments you've had — a song, joke, conversation, place, film, food?
Using these as a guide, I gave more details. Things they liked as hobbies, a little bit about what they were like as a person. I didn't want to just list obvious things, or try to guide it towards a certain outcome (yep, my mate Heisenberg on my shoulder again). I deliberately didn't mention their favourite football team, books or music to start with. I wanted to give a sense of them without mentioning brands or the like.
It came back with themes and categories to consider: the 5 categories below and 12 actual ideas.
Something analogue and beautiful
Something audio-based
Something playful + thoughtful
Something for the senses
Something experience-focused
I discounted 'something for the senses' straight away, and also 'something audio-based' as the ideas themselves just weren't speaking to me. A scented candle - way too girly - and I'm not going to give an Audible gift card; I don't care how useful or clever my suggestions for using it would be. Spotify playlist - done that. And for someone who almost definitely has dozens of "borrowed" pub pint glasses in their kitchen, the suggestion of a personalised Guinness glass was definitely a no.
I fed this back, what I was ruling out and why, and then some thoughts and preferences on the other three categories. This time the suggestions were specific, but not completely within the rules I'd laid out. And some were just not practical (large art print), or beyond me - I'm not going to hand curate 5-10 interesting chess puzzles 'for commuting' or put together a mini-zine! I felt like the chat was derailing into art-project territory, and I'm not 8! And neither are they.
I had to go back to the rules at this point, and prompt specifically:
Just give me 3–5 real, purchasable gift ideas (ideally in the categories we've been exploring) that are thoughtful, a bit understated, and not too DIY.
This went much better. I got some nice pictures of a beautiful wooden chess set, notebooks, links to art exhibitions. Not that I was going for these things exactly, but I had links to click, prices to consider. However, these all felt a little bit like side gifts or stocking-fillers, and quite under budget. I asked it to focus on one main present that was thoughtful, tactile, and a bit more substantial.
The next set of suggestions were far better and veering towards something more appropriate. I asked it for alternatives several times, and we got further towards what I might consider. It even suggested a few things I know this person already has, like Airpods. So, getting more insightful, but also totally useless. And some aren't right for birthday presents, just fun ideas of things to do, and smaller items that whilst very thoughtful, just didn't seem enough. With a refocus on the rules again, eventually I whittled it down to a choice of two: which I'm not going to reveal. They're both good enough to go on my 'oh yes let's save that for later' list.
Finally, to satisfy mostly my own curiosity and with Heisenberg spinning in his grave, I decided to steer it towards what I had thought of myself. If I gave specific enough detail, would it actually be able to find what I'd chosen? Disappointingly, it didn’t. It came close. Really, really close. Let's say the exact thing, but the wrong flavour. Why it couldn't find it, I'm not sure - the website I used to complete my purchase was listed in some of the suggestions it made.
Buying gifts isn’t just about knowing what someone likes - it's about knowing them. When to go left-field, when to surprise them; how to choose something both meaningful and practical. This contrasts with what GPT tends to do: pattern-matching, recency bias, brand-safe suggestions. Because an AI just can't compare to my own lived experience - or to the thousands of OOH I see on my commute, daily. Which I really hate to admit, is where I got my idea. I saw it, and said "Yep, that's perfect. I hope they don't buy it for themselves!"
I will definitely use AI for shopping again. But maybe just for things for myself, where I am not going to be so fussy. In the end, I realise choosing a gift, being thoughtful, and (hopefully) seeing a positive reaction - that's all part of it. I'm not going to outsource that to a machine. Not when my reward is a smile, joy, happiness. That should be earned.
And you, whose birthday it is. If you read this? Just know I'll be thinking of you.
Happy Birthday.