I’ve discussed before that you can use live chat to ask for an online coupon at a ton of major retailers. But what about taking it one step further and actually negotiating a lower price via live chat. Can it be done? I’m here to say…it absolutely can. It’s a great way to get a lower price if you’re nervous about doing it over the phone, or worse yet, in-store.

Below is what you need to know, and the products where it works best. Be sure to add this new money saving hack to your online shopping toolbox.

Step 1: Before Completing your Purchase, Start a Chat Session

Whenever you make a significant purchase online (See step 2) be sure to start a live chat session with the website you’re purchasing from and negotiate the price with them.

Politely start a conversation and chit chat for a minute before dropping the bomb.

Then explain that you’re very interested in the item but were wondering if there was any wiggle room in terms of price.

I recently did this with Dell.com on a $999 laptop and was able to get the price down to $947 with just a couple minutes of effort. Here is how the chat session went:

Step 2: Items Where This Works Best

Products where you can absolutely negotiate the price via live chat include significant purchases like a new computer, major appliance, HDTV, expensive suit, shoes, tools, and fitness equipment.

Also, it’s important to be aware that this will definitely work better on items that are relatively expensive, think “top of the line” laptops, appliances, and consumer electronics.

There is typically more wiggle room on these items compared to a budget laptop that is already at a rock-bottom price.

In addition to Dell.com, I have successfully done this at the following websites the past couple years: Hewlett Packard.com, Dick’s Sporting Goods, JCPenney, Sierra Trading Post, and even Kohl’s.com where I was able to negotiate the price on a Keurig 2.0 K250 coffee maker from $149.99 down to $119.99.

Step 3: Get the Lower Price, Then Use a Coupon Code

Always negotiate a lower price before you add a coupon code to your order.

If you add a coupon, then hit up live chat, you’re much less likely to get the price lowered as the operator can tell you’re already getting a reduced price.

5 Reasons to Ask for a Lower Price

It’s important to realize that your chances of success rise significantly if you have a valid reason to ask for a lower price.

Here are a few ideas to get you started:

1. Lower price. Perhaps you found a lower price at a competing website. This makes for great ammunition.

2. Older model. Maybe the model is an older version and will soon be on clearance. Many retailers will lower the price to get rid of it.

3. Shipping costs. The retailer doesn’t offer free shipping while a competing site does offer free delivery.

4. Recently ended sale. A sale event or coupon just expired and you barely missed out on the lower price.

5. Bad customer service. Perhaps you had a bad customer service experience recently. The retailer may try to make up for this by offering a lower price.

Ask the Reader: Have you ever tried to negotiate a lower price via live chat? If so, how’d it go?

By Kyle James

As I have talked about many times, I am a huge fan of trying to figure out the best times to make online purchases to maximize savings in terms of both deals and coupons made available by popular retailers. So I dug back through 17 years of data here at Rather-Be-Shopping and figured out when we get the best deals and coupons sent to us in December.

I then broke the data up by product category and was able to decipher the exact day you should shop in order to get the best price between now and Christmas. Use this info as a helpful guide this year and I really believe you can save some significant money.

Christmas Toys

Saturday, December 9th, 2023: This date falls on a Saturday this year. Last year we saw the absolute best prices and coupons for toys on December 9th.

This also included the number of deals and coupons available at stores like Amazon, Target, and Walmart.

The reason? My best guess is this is when we reach crunch time for toy sales and the incentives begin to be thrown out by retailers in order to cash in on those “semi” last minute shoppers.

Important Note: If your shopping list includes the hot toys of the year you’re going to need to snatch those up when you find them and not wait until the 10th.

See Also: 45+ Stores Offering FREE Shipping on Holiday Shopping (With NO Minimum)

Stocking Stuffers (Small Gifts)

Wednesday, December 6th, 2023: Our data the past seven years shows excellent early-month coupons from “specialty gift” online retailers like Snapfish, Things Remembered, Personal Creations, and Shutterfly.com.

They usually have new coupons starting on December 6th that last a few days.

Shop early in that time period to ensure Christmas delivery.

See Also: Abandon Your Virtual Cart: 17 Stores Who’ll Bait You Back with a Coupon

Apparel, Shoes, and Accessories

Thursday, December 14th, 2023: Cyber Monday is always the best day of the year for online coupon codes at apparel and footwear retailers. Easily save 40-50% off.

So take advantage of the 2nd best day to save and shop online for clothing and shoes which is Thursday, December 14th.

This is also known as Free Shipping Day, a day where hundreds of online retailers offer guaranteed Christmas Eve delivery at no extra charge.

A large majority of online sites like Gap.com, Lands’ End.com, American Eagle, Macy’s, and Old Navy will have fantastic coupon codes to go along with their free shipping offer. A big double win.

Shopping in-store? Be sure to shop on December 14th for the best clothing and footwear deals as many of the sales and coupons will be in-store too.

HDTV’s (Name Brand Variety)

December 1st – 3rd, 2023: So if you’re not buying a new TV for yourself, then you’ll want to wait until late January, early February, when new models are released and last season’s models have their prices severely slashed.

But if you’re buying a TV as a gift, be sure to check out deals between December 1st and the 3rd.

Over the past 10 years in particular, we’ve seen some killer weekend deals 2 weeks out from Christmas from Best Buy.com, Costco.com, and Walmart.com.

Look for deals this year in the 30-40% off range on Samsung, Sony, Vizio, and Panasonic.

Tools and Hardware

Friday, December 8th, 2023: Shopping for tools for Dad, Mom, or Grandpa this year?

I had to throw Mom in there as my Mom is one of the handiest people I know when it comes to DIY projects and home repair/improvement projects. Take a look at the deals available online on December 8th.

The last few years have seen some killer deals and price drops from Home Depot, Lowe’s, Ace Hardware, and Harbor Freight Tools.

Also, shop in-store for tools and hardware from the 9th up to the 14th for some pretty darn good deals, easily in the 20-30% off range.

Not shopping for tools as a Christmas gift idea?

Then wait until after the holidays, several months actually, and shop for tools in the couple weeks leading up to Father’s Day.

By far the best time of year to save on power tools, tool sets, and anything for the garage.

See Also: 14 Retailers Who WILL Price Match Amazon’s Lower Price

Laptop Computers

Saturday, December 9th, 2023: So for the past three years on December 10th, Dell.com and HP.com have hooked us up with some incredible online coupons.

Like $500 off a top of the line Inspiron 15 laptop (the best price of the year) and also allowed shoppers to buy a very capable budget laptop for under $200.

Look for the same this year. Also, check Costco.com for some attractive deals on laptops mid-December.

Last year they offered several great deals on laptops from Dell, HP, Acer, and Toshiba.

Not buying as a Christmas gift and can afford to wait? Wait until graduation season, followed by the back-to-school shopping season when we see our best prices of the year on a new laptop.

Apple Products

No Set Date: The pricing on Apple products can be a bit tricky to figure out. We saw some pretty decent deals on Black Friday as the iPad, iPod, and iPad Mini all saw their lowest prices of the year with some pretty cool gift card incentives to boot.

So what do you do if you didn’t take advantage? The best way to score a deal in December is to buy refurbished Apple products. Savings in the 20-40% off range on iMacs, iPads, iPods, and even the Apple TV.

Worried about the quality of these refurb items? Don’t be. From the Apple Store site, refurbished items “undergo a rigorous refurbishment process to make sure it’s up to Apple’s tough quality standards. We back it with our standard one-year limited warranty.”

PS5 & Xbox Systems

December 12th – 15th, 2023: While Black Friday was a great day to buy video games and new gaming system bundles, fear not as you still have a chance to save money before Christmas.

Every year over the past 8, we have seen some great deals from Gamestop.com, Amazon, Costco, Walmart, Target, and NewEgg.com in mid-December.

In particular, between the 12th and 15th of the month, retailers really offer some attractive incentives to Christmas shoppers.

We have seen new video game titles priced at 35% off the original price and older games at 60% off. Also, look for great deals on the XBox and PS5 systems, especially new system bundles.

Winter Apparel

Thursday, December 14th, 2023: If you’re buying winter apparel as a Christmas gift, you’ll definitely want to shop online on Free Shipping Day which is December 14th this year.

Not only will you get free shipping from hundreds of retailers, but many websites will also have coupon codes available to entice those last minute shoppers.

Not buying for Christmas? Wait until the end of the winter season in March and take advantage of clearance sales on jackets, boots, sweaters, etc.

See Also: ALL the Popular Retailers With Live Chat Operators Who Hand Out Coupons

Jewelry & Wedding Bands

December 4th – 25th, 2023: I have been informed by several jewelers that jewelry stores freeze their prices, independent of gold and silver prices, in the few weeks leading up to Christmas.

So if you are window shopping for a wedding band, now is a pretty darn good time to consider buying as prices could conceivable rise significantly after the holidays.

The same goes for jewelry for your sweetie that you want to wrap and place under the tree.

Fitness Gear & Equipment

Monday, December 4th, 2023: The last couple years we got new coupons and deals for Dick’s Sporting Goods, REI, and Big 5 Sporting Goods on the 5th day of December.

Will it happen again this year? I can’t guarantee it but I have already gotten word from a couple online sporting good stores that they’ll have some great coupons again in early-December.

Another good day is December 14th as Dick’s, Reebok Store, Under Armour, and Puma Store have already announced they will ship for free on that date.

Not buying for Christmas? Shop right after the New Year when retailers offer great deals on fitness equipment and gear. Some of the best prices of the entire year.

Kitchen and Household Stuff

Thursday, December 14th, 2023: December is always one of the best times to buy stuff for the kitchen, bedroom, and family room.

Stuff like bedding, home décor, cookware, dining sets, silverware, small appliances, and kitchen gear.

But exactly when in December is the best day to get an awesome deal?

The answer this year is Thursday, December 14th.

Why? Because the following online retailers have already stated that they will ship items for free (with guaranteed Christmas Eve delivery) on that date: Macy’s, Nordstrom, Pfaltzgraff, Belk, Mikasa, Brookstone, Lenox, and Chefs Corner Store.

Look for even more stores to jump in as we get closer to the 14th.

Ask the Reader: When in December do you tend to find the best deals and coupons?

Happy savings.

By Kyle James

Photo credit to Dafne Cholet.

Why drop $65 for an annual Costco membership when many popular retailers will happily price-match the warehouse club? Or maybe you’re already a Costco member, but when it comes to shopping for electronics, toys, and tools you have your favorite stores and would rather buy everything from a single place. While many retailers don’t consider “membership clubs” like Costco to be direct competitors, and thus won’t match their pricing, their are plenty who absolutely will and here they all are.

NOTE: If you’re going to try and get a Costco price-match at another store without buying a membership, your best bet is to use Costco.com to check out their prices.

Once you find a lower price, simply print out the product page (with the price visible) and use that to get a price-match at one of the stores below. You could also show the product page and price to a store associate via your smartphone.

Also, if you want to physically get in the Costco warehouse and check out their prices, just tell the card-checker at the entrance that you want to use the pharmacy and they’ll let you in, no questions asked.

Best Buy

Best Buy makes it clear that they’ll price-match not only Costco, but all warehouse clubs in your local area. Here’s what you need to know:

• From the Best Buy website, “We do match the prices of Warehouse clubs as long as the Warehouse club is a local retail competitor, has an identical immediately available product and all other price match criteria are met.”
• Before you ask, a local competitor must be within a 25-mile radius of your local Best Buy store. So if you have a Costco within 25 miles of your Best Buy, you’re good-to-go.
• The fine print reads that the Price Match Guarantee covers 1 price match per identical item, per customer, at the current pre-tax price available to all customers.
• Top Brands in Common: Samsung, LG, Apple, Vizio, Sharp, JVC, Canon, Nikon, Bose, Sony, and Yamaha.

Fry’s Electronics

While somewhat confusing, the Fry’s Price Match Policy most definitely includes Costco. Here is the full scoop:

• Only works on “brand new, unopened products of the same exact model with same warranty.”
• Simple show evidence of the Costco price via your smartphone or printed product page from Costco.com and they’ll hook you up with the lower price.
• Yes, there are some exclusions: Rebates, special program or educational discounts, bonuses, free offers, gift cards, rewards point redemptions, coupons, promo codes, bundled items, or one-of-a-kind or limited-quantity offers.
• Top Brands in Common: Toshiba, HP, Lenovo, Dell, Acer, Alienware, Apple, Samsung, Microsoft, Sony and Xbox.

See Also: 7 Ways to Essentially Get a Costco Membership for Free

Home Depot

A quick phone call to my local Home Depot and yes, they’ll absolutely match Costco prices.

• Not only will the Home Depot match Costco in price, but they’ll actually beat them by 10% on in-store purchases.
• The price must be the regular retail prices at Costco which shouldn’t be an issue unless the item is marked as a manager’s special.
• Items at Home Depot where a price match is possible include storage and organization items, wrench sets, ladders, and power tools like cordless screwdrivers and drills.
• Exclusions: Special orders, bid pricing, volume discounts, open-box merchandise, labor and installation, sales tax, rebate and free offers, typographical errors and online purchases.
• Top Brands in Common: Dyson, Lifetime, Bissell, Calphalon, Honeywell, Master Lock, Duracell, Feit Electric, and Coast Flashlights.

Kohl’s

Kohl’s will happily price match Costco items with a few stipulations.

• Items must be identical and in-stock at both stores.
• Can’t get a price match during Thanksgiving week or the week after.
• Kohl’s does reserve the right to limit the number of items you can price match.
• Top Brands in Common: Google Nest, Netgear, Xbox, Apple, Cuisinart, DeLonghi, Keurig, and KitchenAid.

Lowe’s

Here’s how the Lowe’s price-match policy works:

• The only time Lowe’s won’t match a lower Costco price is when the item is a closeout, special order, clearance, liquidation, damaged, or simply being discontinued.
• While Costco and Lowe’s don’t stock many of the same items, you can definitely find identical items when shopping.
• Top Brands in Common: Little Giant, Stanley, Kwikset, Dyson, Energizer, Leatherman, and Safety 1st.

Petco

The Petco Price Match Guarantee also includes price matching Costco products.

• Items must be identical and in-stock at both locations.
• Just show the lower Costco price to any employee and they’ll help you get your savings.
• Can’t be combined with any coupons or Petco special offers.
• Top Brands in Common: Advantix, NexGard, You & Me, Kong, Nutro, Avery, Iams, and Purina.

PetSmart

When shopping for pet food, supplies, beds, and treats, be sure to get the Costco price from your local Petsmart. Here are the details:

• Items must be identical in size, and currently in-stock at both Costco and Petsmart to qualify for a price match.
• Show evidence of the lower Costco price to any sales associate.
• They won’t match prices that are advertised as clearance, BOGO, rebates, liquidation or other special events. Also, price matching is not valid on pets and services which shouldn’t be an issue as Costco doesn’t sell cats or dog grooming.
• Top Brands in Common: Frontline, Advantage, PetArmor, and PoochPads.

Sam’s Club

While Sam’s doesn’t have an official policy, I was able to do some digging and discover that Sam’s will indeed price match Costco. Here are the details:

• Sam’s Club will price match local competitor’s pricing on identical items. Apparently, the only 2 competitors that they’ll match are Costco and BJ’s Wholesale Club.
• You also have 7 days after your purchase to get the lower Costco price if you find it.
• Top Brands in Common: Pretty much everything, other than their exclusive store brands Kirkland and Member’s Mark. The key here is to find identical specs in terms of package size and servings.

Staples

Staples will also happily price Costco on identical items. Here’s the skinny:

• From the Staples website, “Staples will price match items sold by any retailer who sells products in both retail stores and online under the same brand.” Costco and Costco.com fit the bill. I also went ahead and double-checked, via Staples live chat, that they consider Costco a “retailer” and not a “wholesaler” and they absolutely do consider Costco a “retailer”.
• Simply show evidence of the lower Costco price when purchasing the identical item from Staples. This can be done in the form of a picture of the Costco price tag (and product) taken from your smartphone, or a print-out directly from Costco.com.
• Items to look for a price match include technology like laptops and tablets, basic office supplies, along with organizational/storage products.
• Top Brands in Common: Very similar to Office Depot above.

Target

The official Target price-match policy was a little vague about Costco.

So I started a chat session and here is how the conversation went…

Sarah: Thanks for shopping on Target.com. My name is Sarah. How can I help you?
Kyle: Hi Sarah, do you guys price-match Costco?
Sarah: Kyle, let me check and help you with the information.
Sarah: We should check the item and the model number of the item to price match.
Kyle: So…do you guys price match Costco? Yes or no?
Sarah: Yes, Kyle.

• While they officially started price matching Costco on October 1st, 2015, they will now also price match “brick & mortar” Costco. I tried to get the details out of Sarah, but was unsuccessful, so I think it’s safe to assume it works like any other competing retailer.
• They’ll match the price on a single qualifying item when you find the product for less at Costco or on Costco.com.
• Price matches may be requested at the time of purchase or via a price adjustments within 14 days after purchase.
• All Target price matches, and adjustments, are completed in-store at the ‘Guest Services’ desk.
• Top Brands in Common: Dyson, Lexmark, Disney, KitchenAid, Keurig, Garmin, Fisher-Price, Huggies, Pampers, Apple, Lego, and Rubbermaid.

While it can seem a bit tricky to find identical products at Costco and all of the above retailers, it absolutely can be done. The key is to consider what brand-name items are sold at both retailers, then start price comparing like a madman.

Happy savings, and more importantly, happy price-matching.

By Kyle James

Photo by Mike Mozart.