55 - The Calendar Strategy: How to Automate Your Dining Discounts (And Never Pay Full Price Again)

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I recently did something a little crazy—but financially brilliant. During the holiday sales, I stocked up on restaurant gift cards. You know the ones: “Buy $100, Get $25 Free.” I bought them for my favorite local spots: the Irish pub around the corner, the pizza place we love on Fridays, and the nice steakhouse we save for special occasions. Mathematically, I was already winning. By getting $125 worth of food for $100, I had locked in an instant 20% discount on my future meals. But then I thought: How can I stretch this even further? The gift cards are great, but they are only one part of the equation. Most of these restaurants also offer weekly specials—Half-Price Burgers on Mondays, Taco Tuesdays, Kids Eat Free Wednesdays, or Happy Hour appetizers. If I used my discounted gift cards only on nights when the food was also discounted, I wouldn’t just be saving 20%. I’d be saving 50%, 60%, or even 70% off the regular menu price. The problem? I can never remember which restaurant has the ...
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2 - Use grocery store apps and restrict yourself to the sale items.

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The best grocery store app near me is for Jewel-Osco. Their app is great and is easy to find the best deals. I don't do anything ahead of time - I just add things to my "cart" as I shop around the store. At Jewel, items that are on sale through the app have blue signs in the store, so I know to find the deal in the app before literally adding the item to my actual shopping cart.

There are also great deals to be found throughout the store that require a bar code scan in order to get the sales price. I've found that most of these deals are incredibly cheap and often only offered once or twice per period of time per customer. Last week, I got ten Yoplait yogurts for 9 cents each. And eggs have been about half price these days when scanning the bar code!

Additional Tips and Directions from AI:

Using grocery store apps and limiting your cart to sale items is a universally smart way to protect your budget. Here’s how anyone in the U.S. can make the most of these strategies—whether shopping at Jewel-Osco or any major grocery chain like Kroger, Safeway, Albertsons, Publix, or Meijer:

Step-by-Step: How to Maximize Grocery Savings With Store Apps

Download your local store’s app: Search the name of your grocery store (e.g., Jewel-Osco, Kroger, Food Lion) in the app store and create a free account.

Link loyalty/rewards and digital coupons:

  • Connect your app to your store’s loyalty card or phone number to activate digital-only deals and get personalized discounts.
  • Most apps allow you to “clip” digital coupons—just tap to add them to your account for instant savings at checkout.

Shop in-store using only sale items:

  • As you walk through, look for the app’s discount tags (often blue, yellow, or red signs). If you see a price marked as an “app exclusive sale,” open your app and add the item to your digital cart or tap “clip deal.”
  • Restricting yourself to only these deals keeps your grocery budget tight and ensures you’re always getting the store’s lowest prices.

Take advantage of barcode-only and scan deals:

  • Many modern grocery apps feature limited-use “scan-to-save” offers—often for deep discounts or freebies.
  • When you see an item with a special barcode in the store, scan it using the in-app barcode scanner to unlock the lower price. Some deals are only available for a set number of redemptions or once per account.

Review your cart before checkout:

  • Check your app’s “My Cart” or “My Deals” section to confirm everything is activated.
  • At the register, enter your phone number or scan your app’s digital card to automatically apply all app-linked discounts.

Extra Tips for Maximum Savings, Nationwide:

  • Compare between grocery chains in your area—most have free apps with digital coupons (Kroger, Safeway, Stop & Shop, etc.).
  • Always check the “Weekly Ad” or “Featured Deals” section of the app for the best sale prices before heading to the store.
  • Use in-app filters to find the lowest prices or biggest discounts on the products you buy most, like produce, dairy, or snacks.
  • Stack manufacturer coupons (if allowed) on top of store app deals for extra savings. Some chains let you stack these at the register or within the app.
  • Don’t forget about “clip once” or “limited redemption” barcode specials—these are often the absolute best deals and great for stocking up.
  • Enable push notifications or app alerts for flash sales and limited-time discounts so you don’t miss rock-bottom pricing.
  • Master these app techniques, and you’ll see huge savings on your grocery bill every month—no pre-planning or coupon clipping necessary!

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