My sister and I lived together for a short time, and we tried our best to split bills 50/50. The grocery bill, however, was our biggest source of contention. Whereas she would shop for whatever she needed at the time and pay full price, I was a couponer who stockpiled and hunted for deals. So our 50/50 arrangement for groceries quickly became lopsided, and I didn't look forward to paying my half of the bill when I practiced a completely different method of spending in contrast to my sister.

Fast forward five years…my sister and I are living in separate homes and have separate lives, but there's one characteristic we share—we're both adept couponers! So how did I turn my spend-a-holic sister into a KCL? With a little patience and some couponing ingenuity, it wasn't as hard as you might think.

So if you are living with a couponing skeptic, here's what I suggest you do to help that individual understand the world of grocery store savings opportunities:

1. Start small

Combining coupons, sales, price-matching, refunds and cash-back apps are great ways for KCLs to get products on the cheap or even as moneymakers. But as enticing as getting $55 worth of products for free is, this Ibotta combination trip might be too complicated for a first-time couponer. Instead of expecting a skeptic to understand the world of couponing immediately, go at it a bit more slowly. Introduce the skeptic to one deal or weekly store offering at a time. For example, instead of the above Ibotta deal, I might introduce a skeptic to select items on this weekly Wal-Mart matchup and show her how to get completely free Wet n Wild nail polish or get cash back right at the register after buying three Gillette shave creams. Simple, high-value transactions with an easy-to-understand savings percentages are one way to hook skeptics.

2. Give the skeptic the good coupons

All KCLs know when they've found a really good coupon: it might be for a high value, it might be a BOGO offer, or it might result in the product becoming a moneymaker. While it can be fun to get these deals ourselves, these are the deals that turn into golden teaching opportunities for skeptics. When I took my sister to the grocery store with me, I let her choose the type of flavor for a four-pack of yogurt I had a free coupon for (that I received directly from the manufacturer by making a request). She couldn't believe we were walking out of the store with a free product! When it was her turn to shop next, I casually asked if she could pick up a BOGO deal on disinfecting wipes at the store but also handed her a 55-cent-off coupon, knowing she could use it on the first item while the store automatically subtracted the $2.49 cost of the second item. Each canister then cost less than $1, and she was thrilled to see this for herself. These good deals quickly converted her to a KCL way of thinking.

3. Let the skeptic shop for fun products

A couponing skeptic is much more likely to turn into a believer when deals that are meaningful and fun to them are available. For example, is your skeptic a cosmetics lover? Find deals that will help her score great products at a killer price. For instance, this past week, my H-E-B store was selling certain colors/styles of Sally Hansen Nail Effects at half price: they were marked from $8 to $4. H-E-B also displayed yellow store coupons for $3 off any Sally Hansen product in that particular line. So an $8 product very easily turned into a $1 product! Even a shopper who is poor at math can calculate this outstanding savings.

4. Empower the skeptic with matchups

Someone who is new to couponing and uncertain about the savings potential is not going to sit down and map out a savings strategy for an upcoming shopping trip, so don't expect the skeptic in your life to do so. Instead, you can handily print a shopping matchup from the "Find My Store" tab of the KCL site or introduce her to the "Beginners" section of the site to zero in on a few important deals. Armed with this information and guidance, the skeptic can begin shopping and seeing the savings percentages for herself, with minimal preparation time and shopping effort.


What have we failed to mention? Use the "Comments" section below to share your own stories and techniques for turning a skeptic into a KCL.