Jennifer Jolly on The Sunday Briefing: Here’s the Holiday Shopping Advice I Shared On-Air
Your guide to smarter shopping, fewer headaches, and avoiding holiday-season scams.
If your holiday shopping feels a little… different this year, you’re not imagining it. Artificial intelligence is everywhere, people are angrier with retailers than they’ve been in decades, and porch pirates have turned package theft into an $8 billion business. I was just on the Sunday Briefing talking about all of this. Here’s the deep dive on what you need to know now.
AI is now doing part of your shopping — for better and for worse:
Target and Walmart both rolled out AI-powered chatbots that act like personal shoppers. Once you’re logged into your account, you can type something like: “I need a gift for a 10-year-old who loves space, and my budget is $40.” Their bots instantly filter options, show what’s in stock, and summarize reviews. It’s fast and surprisingly helpful.
Amazon stepped even further into the future. Its new AI system, Rufus, now tracks price drops, compares similar products, and can even place the order automatically when something hits the price you set. It’s free, built right into the Amazon app, and you don’t need Prime to use those AI features — although some delivery and shopping perks still require membership.
Google is testing something that feels straight out of science fiction: an AI assistant that will call local stores for you. You search “PS5 in stock near me,” tap a button, and Google’s AI places automated calls to ask about inventory, pricing, and sales. Minutes later, you get a summary so you’re not driving around town guessing.
What you do to use it:
Open Google Search and type or speak your shopping request (e.g. “4-year-old girl toys near me,” or “PlayStation 5 stock near Oakland”).
If the AI-powered features are live for you, you’ll see a new option — a button like “Let Google Call” in search results or shopping listings.
Tap that, fill out a simple form (item, quantity, maybe ZIP code or store radius), hit “Confirm,” and Google will — using its AI/voice-call technology — call local stores for you to check inventory, price, and whether it’s on sale.
Google will then deliver a summary of responses (available store, price, etc.), often by text or email.
Inside ChatGPT — including the free version — you can now ask for gift ideas, compare brands with photos and links, and even hit “buy” on Etsy or Shopify without leaving the chat. The more advanced, faster version is $20 a month.
The upside? These tools save time and help you cut through the noise of endless choices. The downside? They’re still early. They repeat recommendations, miss whole brands, or occasionally make things up — “hallucinate.” Remember: scammers use AI too. Fake ads, fake discounts, fake stores — all generated faster and more convincingly than ever.
So the rule is simple: Use AI for speed. Use your judgment for checkout. Always verify the retailer and the URL before you pay.
People are angrier with retailers than at any point in 40 years
This is the part that hit home on the show this morning. People feel duped. Companies make it incredibly easy to buy something in seconds, but make people fight to fix even the simplest problem. You can get dental floss delivered in 30 minutes, but you can’t get a human on the phone in 30 hours. That mismatch is driving people over the edge.
The National Customer Rage Survey shows:
77% of Americans had a product or service problem this year — the highest ever
68% say complaining requires “high effort”
And Forrester’s annual customer-experience index shows four straight years of decline
People aren’t imagining this. Retailers are quietly:
Shrinking return windows
Adding more return fees
Burying cancel buttons
Pushing shoppers into chatbots that stall, not solve
And many companies now reserve faster service for premium, high-status customers — everyone else waits. Upper-income shoppers report almost twice the satisfaction with resolutions.
What can you do about it?
Use your credit card as leverage.
If a retailer won’t help, your credit card issuer often will — disputes, refunds, travel credits. The card company has real power.
Use tech that advocates for you automatically.
Tools like Capital One Shopping, DoNotPay, Paribus, Refundify, and Refundly help request refunds, track packages, or get credits when deliveries arrive late or prices drop.
Stick with retailers who still treat people well.
Chewy, Apple, and Costco consistently rank among the highest for customer service.
You can’t force companies to care — but you can protect yourself with better tools, better retailers, and a clean paper trail.
Porch pirates are stealing more than ever — and this holiday will be their biggest haul
One in four Americans has had a package stolen. Nine million adults lost at least one package in the last three months alone. Thieves took more than $8.2 billion in items off porches over the past year.
This isn’t petty theft anymore — it’s organized, fast, and opportunistic. Thieves follow delivery trucks, watch for boxes piling up, and hit neighborhoods repeatedly.
But here’s the good news: the simplest solutions work best.
Deliver to an Amazon Locker or UPS Access Point. Ship to your workplace. Or schedule deliveries for times you’ll be home. Doorbell cameras and motion lights deter many thieves, but hiding the package works even better — choose “deliver to side door,” leave a note, or bundle everything into one “Amazon Day.”
I’ve also been testing new lockable devices designed for this problem — Hyve, a secure delivery box, has stood out as a simple, surprisingly effective option.
And remember: many major retailers replace stolen items if you report fast, and most credit cards include purchase protection for 60–90 days. Don’t just accept the loss — you have recourse.
For more ways to save money, avoid scams, and use tech that actually makes life easier, subscribe at Techish.com and listen to Techishly Jenn wherever you get your podcasts.