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Hey, it’s Jeffrey — back again!
It's mid-November. You have 10 people to buy gifts for. And there's always that one person who's impossible to shop for.
You know the type: mid-60s, has everything they need, buys what they want, and when you ask "what do you want for the holidays?" they say "nothing, really."
For me, that's my father-in-law.
So this year, I decided to let AI do the heavy lifting. I tested 5 different AI gift finders with the same challenge: Find a great gift for a guy in his 60s who has everything.
Same person. Same budget. Five different tools.
Here's what actually worked — and what was a complete waste of time.
📬 In this email:
The Test: One Person, Five AI Tools
1️⃣ Amazon's Rufus AI
2️⃣ Giftlist.com Genie
3️⃣ Target's Gift Finder
4️⃣ Google AI Mode
5️⃣ ChatGPT (Control Test)
🏆 The Winner
💡 One Smart Read
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The Test: One Person, Five AI Tools
The Challenge:
I gave every AI tool the exact same information:
I need a gift for my father-in-law. He's in his 60s and it feels like he has everything.
His interests:
- Travel
- Golf
- Bourbon
- Wine
- Cigars
- Boating
He's not a gadget guy. He likes nice shirts (we've done William Murray and Untuckit before). Budget: $100-150.
What should we get him?I wanted to see which tool would give me:
The most creative ideas
The most practical suggestions
Something I hadn't already thought of
Let's see how they did.
1️⃣ Amazon's Rufus AI
What it is: Amazon's AI shopping assistant built into the Amazon app and website.
How it works: Type or paste your prompt directly into the Rufus chat interface. It pulls from Amazon's massive inventory and shows you actual products with prices and Prime shipping.
What it recommended:
LIITON Mountain Crystal Decanter Set - $129.99
Crystal decanter with 4 glasses, mountain peak design
Luxury Wine Gift Set with Electric Opener - $139.99
Rechargeable opener with 3-in-1 aerator and vacuum pump
Rustic Town Handmade Leather Duffel - $149.45
Full-grain leather carry-on with TSA approval
Xikar Travel Humidor Case - $108.99
Waterproof, holds 20 Churchill cigars
Plus several more options across bourbon, wine, golf, and travel categories.
The verdict:
✅ Pros:
Actually showed me specific products I could buy right now
Real prices, real availability, Prime shipping info
Wide variety across all his interests
Easy one-click purchase
❌ Cons:
Some recommendations felt like "what's popular" rather than "what's thoughtful"
Limited to Amazon inventory (no recommendations for experiences or non-Amazon items)
A few gadget-y suggestions despite me saying he's not a gadget guy
💰 Best for: Someone who wants to shop on Amazon and likes seeing exact products with real prices immediately
My take: Rufus is the most practical if you're actually ready to buy. It showed me things I could purchase in 2 minutes. The leather duffel and crystal decanters were legitimately good ideas, but some suggestions (like the electric wine aerator) missed the mark on "not a gadget guy."
Rating: ⭐⭐⭐⭐☆
2️⃣ Giftlist.com Genie
What it is: A dedicated AI-powered gift recommendation platform designed specifically for gift finding.
How it works: Simple chat interface where you paste your prompt and get curated recommendations.
What it recommended:
Orvis Whiskey Signal Golf Ball Markers Set
Elegant markers combining golf and whiskey themes
Davidoff Nicaragua Toro Cigars Gift Box
Premium cigar gift box from a renowned brand
Vince Camuto Striped Performance Polo
High-quality leisure polo for golf or boating
Riedel Vinum Bordeaux Wine Glass Set (4 pieces)
Top-rated fine wine glasses
Saddleback Leather Travel Dopp Kit
Rugged luxury toiletry bag for travel
It recommended a few more similar items too.
The verdict:
✅ Pros:
More curated feeling than basic product searches
Good variety across price points
Direct links to purchase
❌ Cons:
Some odd recommendations that missed the mark (one suggestion was just an empty cigar box for collectors, not actual cigars)
Interface isn't as polished as other options
Claims to work with a variety of retailers, but results only came from Amazon in my search
Doesn't always understand product details well
💰 Best for: Someone who wants a simpler list of items in a succinct format.
My take: Giftlist gave me a decent starting point, but it's clear the AI doesn't always understand what it's recommending. The golf ball markers were creative, and having direct purchase links was helpful, but the interface felt clunky and I was skeptical about some suggestions.
Rating: ⭐⭐⭐½☆
3️⃣ Target's Gift Finder
What it is: Target's new AI-powered gift recommendation tool launched for the 2025 holiday season.
How it works: Web-based interface that requires you to go through a step-by-step questionnaire. It wouldn't accept my full prompt at once—I had to answer multiple questions in their format.
What it recommended:
Target showed me broad product categories rather than specific gift ideas:
Luggage - Travel sets ranging from $129-$328
Golf Clubs - Complete sets from $279-$429
Golf Accessories - Small items like drawstring bags and club grips ($11-$29)
Wine Chilling Buckets - From $34-$149
Plus several other categories like barware sets, serving trays, and coolers.
The verdict:
✅ Pros: Easy to browse Target's inventory, clear pricing and availability
❌ Cons:
Wouldn't accept my full prompt - forced step-by-step process
Results felt generic, not personalized to his specific interests
Limited to Target.com inventory only
Showed broad categories instead of curated gift suggestions
💰 Best for: Someone who specifically wants to shop at Target and prefers browsing categories over specific recommendations
My take: Target's tool feels more like a category filter than an AI gift finder. It didn't consider the nuance of "he has everything" or suggest anything particularly thoughtful. It wasn't really all that more useful than using a basic search function.
Rating: ⭐⭐☆☆☆
4️⃣ Google AI Mode
What it is: Google's AI-powered search experience with AI Overviews that synthesizes information from across the web.
How it works: I searched with my gift prompt and got an AI-generated response pulling from multiple sources, plus product examples.
What it recommended:
Google gave me strategic advice first, then specific suggestions:
Strategy:
Focus on "quality, experience-enhancing items rather than gadgets"
"Classic, well-crafted pieces that enhance experiences he already enjoys"
Product categories:
High-End Leather Goods - Dopp kits, belts, travel journals
Premium Whiskey Accessories - Quality whiskey stones, Glencairn glass sets
Handmade Cigar Humidors - Spanish cedar with analog hygrometers
Bespoke Golf Accessories - Leather scorecard holders, custom tees
Specific products:
LIITON Mountain Crystal Decanter - ~$130
Handmade Leather Travel Duffel - ~$149
Spanish Cedar Humidor (ammo box style) - ~$120
Eureka Golf Gift Basket - ~$145
The verdict:
✅ Pros:
Most thoughtful approach to the problem
Explained WHY each type of gift works
Balanced strategic thinking with actual products
Understood "not a gadget person" better than others
❌ Cons:
Doesn't link directly to products - links go to review websites instead
Annoying to click through to a review site, then have to figure out where to actually buy
Still requires extra research after getting recommendations
💰 Best for: Someone who wants to understand the thinking behind gift choices and doesn't mind doing extra legwork to find where to buy
My take: Google AI felt like talking to a thoughtful friend who actually listened and understood the assignment. But the user experience was frustrating - clicking through to review websites that just talk about products instead of letting me buy them was a dealbreaker.
Rating: ⭐⭐⭐☆☆
5️⃣ ChatGPT
What it is: The general-purpose AI you probably already use.
How it works: I pasted the same prompt directly into ChatGPT and got a detailed response.
What it recommended:
ChatGPT gave me three gift themes instead of just a product list:
Theme 1: "Travel-ready golf" - Premium travel covers and accessories that bridge his golf and travel interests, like the Samsonite Golf Travel Set or TUMI Golf Pouch.
Theme 2: "Cigar or bourbon luxury accessory" - High-end items like premium leather humidors, quality decanter sets, or bourbon tasting kits that complement hobbies he's already invested in.
Theme 3: "Boating-inspired but elevated" - Thoughtful items like premium marine polos, high-end cooler bags, or personalized leather boat log books that tie into his lifestyle without being gadget-heavy.
ChatGPT's recommendation: Go with the travel golf gear (hitting both interests), maybe paired with a smaller cigar accessory for a two-part gift.
The verdict:
✅ Pros:
Most strategic thinking of any tool
Explained the "why" behind each suggestion
Gave me frameworks instead of just lists
Understood "he has everything" meant I needed thoughtfulness, not just stuff
Provided direct shopping links with different store options for each product
Interface was neat and well laid out with clear pricing
❌ Cons:
More reading required before taking action
💰 Best for: Someone who wants a shopping strategy, not just a shopping list
My take: ChatGPT was the only tool that helped me think like a good gift-giver instead of just a shopper. The "travel-ready golf" theme gave me a clear direction, and having direct shopping links to multiple stores made it easy to compare options. The interface made everything feel organized and thoughtful.
Rating: ⭐⭐⭐⭐⭐
🏆 The Winner
ChatGPT wins — but not because it gave me the most products or the fastest path to checkout.
It won because it actually helped me solve the problem: finding a meaningful gift for someone who has everything.
Here's what ChatGPT did differently:
✅ Gave me gift strategies, not just product lists
✅ Explained why each idea works for this specific person
✅ Helped me think beyond "what can I buy" to "what would actually matter"
✅ Understood that "he has everything" is a cue to be more thoughtful
Honorable mention to Amazon Rufus AI, which I'm probably nearly as likely to use, especially if I'm shopping on Amazon exclusively
💡 One Smart Read
You Won't Be Able to Offload Your Holiday Shopping to AI Agents Anytime Soon // WIRED
Behind the scenes, OpenAI, Google, and Amazon are battling over who gets access to your shopping data and chat history. The result? AI shopping tools that still need tons of human oversight. This explains why every tool I tested required me to make the final call—we're still years away from AI that can actually shop for you.
🎯What to Do Now
✅ Think of your hardest-to-shop-for person
💬 Copy my prompt format above and try ChatGPT first
🛒 Use Amazon Rufus or Google to find the actual products
🎁 Buy with confidence knowing you actually thought it through
📤 Know someone stressing about gift shopping? Forward this email
How did you like today's newsletter?
One quick note: This newsletter is for educational purposes only and does not constitute financial advice. I'm not a financial advisor — just someone sharing ideas and tools I've found useful. Use what works for you, skip what doesn't, and always do your own research. Some links may be affiliate links or sponsored content for which I may receive compensation.