I Asked AI Chatbots for Gift Recommendations, and It Went Horribly

I've never been great at picking out thoughtful presents. I’m not the worst at presents, but I’m inconsistent. Sometimes I hit a triple and sometimes I’m tagged out at first, but I never hit that grand slam “I never knew I always needed this” present. My obligatory gifts usually go well—I give thoughtful and appropriate Secret Santa gifts to co-workers—but when I'm choosing a present for someone I love, I get overwhelmed and paralyzed searching for an object that measures up to the feelings I have, so I end up stopping at CVS and buying them a pack of batteries or something. Maybe I’m reading too much into it, but it makes me wonder if I’m not empathetic or caring or creative enough to be an all-time great present-picker-outer. So I turned to AI for an assist.

From piloting automatous vehicles to diagnosing cancer to letting us hear what it would sound like if Hank Williams Sr. sung "Straight Outta Compton," AI is transforming our culture quickly and ruthlessly. But there are some seemingly simple tasks that AI still can't do well—like, as I quickly figured out, picking out a thoughtful gift for a family member. When it comes to matters of the heart, AI just doesn't cut it.

The grifty, depressing world of AI gift recommendation services

There are a lot of websites and apps that promise to use AI to help people find great gifts, so I started my hunt there. Judging by Google search results, over the last few years, hundreds, maybe thousands, of people have secured domain names like “bestAIGift.co," thrown together some HTML, and set up shop in the AI gift industry. It doesn’t seem to be going well for them.

The majority of sites I looked at from the top tranche of Google recommendations have that greasy, thrown-together feel of scam websites, and most of them are broken. DreamGift at least looks legit; the website says it has been featured in the New York Times, and it offers a “personal AI gift shopper” named Bliss who asks questions about your giftee in a chat window. But Bliss doesn’t provide the suggestions she promised. When I used it, Bliss just timed out, like someone stopped paying the bill on the plugin. 

Of the AI gift recommendation sites that function, most don’t use “artificial intelligence” as it is commonly understood. Instead, you fill in drop-down menus with the gift recipient’s age, gender, and your relationship to them, and it spits back a generic set of catalog links. (Thanks for the help, Giftbox, but I asked him, and my son does not want “a high-quality skateboard complete with custom grip tape” or “A DIY robotics kit for building and programming his own robots” for his birthday.)

I did find a few working sites that really use large language model AI programs to provide gift advice. But they work by opening a window to ChatGPT or other AI brains, so I decided to cut out the middleman and ask some of the biggest, most advanced AI platforms for help directly. I started each chat with “Can you help me choose the perfect gift for my son’s birthday?” and let the AI direct the conversation from there.

Trying ChatGPT to help find the perfect gift

I started with the most well-known AI: OpenAI's ChatGPT. I put my question in, and ChatGPT responded by asking for information about my son: age, interests, personality, hobbies, etc. I entered them, and it responded with the most generic gift list possible.

I said he liked video games, hip-hop, graphic design, and baseball caps. ChatGPT said I should “research limited edition or vintage baseball caps featuring designs related to his favorite video games, hip-hop artists, or graphic design themes.”

I told ChatGPT that he is intelligent, and it suggested “an interesting book” and “a blank journal.”  

That’s not bad advice or anything, but a book he might like and things related to his interests are so generic that the list is fairly useless. The only specific gift ChatGPT mentioned was "vinyl records of hip-hop artists." I ran that by my kid and he scoffed and said "It's 2024. Who has a record player?"

That said, if you were having trouble understanding how a person’s hobby could be “shopped for” it might help you brainstorm basic ideas.

Rating: 3 out of 5.

Can Microsoft Copilot help you find the perfect gift?

My next stop was Microsoft Copilot. I asked “Can you help me choose the perfect gift for my son’s 17th birthday?” It didn’t ask about him at at all; it just replied with a link to a box of survivalist tools from Temu.

I admire Copilot’s decisiveness, but I’m not sure what my kid would do with a flint stone and “fake shrimp bait” in Los Angeles, and the knife is a little much. Besides, if you’re paying 23 dollars for survivalist gear from Temu, you probably don’t want to survive that much.

I responded to Copilot with “Whoa. My kid is not Rambo. Try again.”  And it immediately sent a link to a “Gentleman’s Gasher” hunting knife. 

I am not sure why Copilot thinks my child should have weapons, but I’m mildly terrified at the implications.

Rating: 1 out of 5. 

Can Qualified’s PiperAI help you find the perfect gift?

Qualified is a B2B company that just launched an “AI SDR” named Piper to help the company “disrupt the modern pipeline generation process by giving marketing and sales leaders a newer, faster way to grow pipeline.” I don’t know what any of that means, but it looks like this:

Here's how our chat went:

A direct approach clearly wasn't going to work, so I tried to speak the AI's language.

A dead end. So I changed tactics:

After more cajoling and coaching, this actually started working, and Piper began planning my kids' party:

But just as I was about about to get the present recommendation...

... a human at Qualified noticed what I was doing and butted in.

So I bid a hasty retreat.

Qualified was cool, and its bot handled my weird request really well, so I'm sure it's great at B2B pipeline-based business metric analytics and quarterly profit stock markets or whatever, but I ultimately wasn't able to determine its ability to recommend a good gift.

Rating: 2 out of 5

Can Claude help you pick out the perfect gift?

If AIs were people, Claude is the only one I'd hang out with. From its presentation to its responses, Claude comes across as warm and approachable. It's not as generic as ChatGPT, it doesn't think my son should have weapons like Copilot, and it isn't a hard-driving careerist like Piper. Still, its initial gift list was was nearly as generic as ChatGPT's.

But I realized maybe the problem was me. Maybe I hadn't gotten specific enough about who my son is, who I am, and what the gift a father gives to his son on his 17th birthday means to us both. So I opened an emotional vein and spent hours (literally) telling the machine everything about myself, my son, and our relationship. (AIs are good listeners.). Then I asked it for the ultimate recommendation: Here's what it said:

I would have never thought of that gift! So maybe it was actually the perfect present. I asked my son what he would think if I got him a vintage typewriter for his birthday and he thought the idea was hilariously, laughably terrible, "the worst present you could possibly get me." Worse than anything off the list of generic gifts from ChatGPT.

Rank: 1 out of 5

Conclusion: don't use AI to help you pick out presents

AI is bad at picking out presents for the same reason it's bad at telling jokes. When AI isn't being psychotic like Copilot, it works by analyzing billions of sentences and picking out the most likely response to a question without weighing whether its sources are good or bad. It's aiming for the middle, so any joke it tells is going to be mildly amusing and never wildly creative, and the gift list it provides is always going to be "a blank journal" or "an interesting book." If you press for details, the interesting book will be a book that the most people other people have called "interesting"—in other words, a book that isn't interesting at all.

Although running AI's suggestions by my son was hilarious, and we ended up having a long, interesting conversation about AI's limitations and how funny but also scary it is when AI gets things wrong. So maybe that was the gift the artificial intelligence was guiding me to all along. Or not. In the end, I'll probably just get him some Steam cards.