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Grocery Shopping for the Mildly Obsessed

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AUTHOR: Andrew Forsythe on 1/05/2026

And now, as Monty Python might say, “For something completely different….”

Given the recent discussion as to which topics are, and are not, appropriate for HD’s realm of finance and retirement, let me first give my defense of an article on the mundane topic of grocery shopping. It’s really pretty simple: For us at least, our weekly expenditures at our friendly local HEB are one of our most substantial fixed costs, probably around $8000 – $10,000 every year. Now with that out of the way…..

I’ve shared before the story of how I went from carefree bachelor to husband and father of four in very short order. In the early days of that new status, and with 2 of our 4 kids in the baby/toddler stage, the home front was a place of constant chores, including the dreaded diaper changes. So when an opportunity arose to get out of the house and go grocery shopping, I quickly volunteered. That was 38 years ago, and I still perform the role.

The list of things I’m not good at would fill a large book, but one thing I can do, practically in my sleep, is organize. In addition, on realizing that I now had four college educations to fund, my spendthrift bachelor habits turned on a dime and I became an instant tightwad (or “value investor” as I like to think of it). So the job of grocery shopping actually was a natural for me.

The first order of business was to create a standardized grocery list which could be used each week and was easily modified. Importantly, it also needed to follow the geography of the store. So I put together a Word document containing all the items we routinely buy, organized in columns in the order in which they’re located in the store in accordance with my usual shopping route.

The list is placed on the fridge and during the week we simply circle the items we need. New or different items are handwritten in the margins, in the appropriate place according to their location in the store.

The store, naturally, likes to throw curveballs and periodically rearranges item locations. But the order of the list can be easily revised to sync with the changes.

Shortly before the shopping trip, I add to the list (in red ink) all that week’s coupons I intend to use. HEB helpfully posts these online, so they’re easy to add. They can be “clipped” digitally using my laptop, and are automatically added to my phone. When I check out at the store, the cashier scans a bar code on my phone, and all the coupons are automatically applied.

Before proceeding I should note that, as to this article’s title, my wife would delete the “Mildly” qualifier. But I have a defense for that as well. I’ve long been a coupon clipper, but years ago I stumbled on a few websites—one was called “Krazy Coupon Lady” I seem to recall—and I saw what a true fanatic looked like. There was a whole universe of extreme coupon clippers who put me to shame. Through incredibly complicated maneuvering, they would walk into, say a CVS, and walk out with a huge amount of items for which they paid literally cents on the dollar. So, yes, I consider myself only “mildly” obsessed (“Take that, my dear!”).

I know there are those who check the weekly specials and coupons at several grocery stores, and will shop them all in order to get the featured deals at each. Again, being only mildly obsessed, I can’t do that—too much time and too many miles. Moreover, knowing your store, and sticking with it, has benefits. The principal one is that by knowing where everything is, you can move fast.

Another aspect to coupons is noting the approximate total when I complete my weekly list. The checkout stand is usually a hyper-busy spot, and I’m not going to be “that guy” who jams things up by raising a thorny coupon issue there. So I’ve learned to check my receipt before leaving the store. With some frequency, a coupon will be missed, so I then head straight to the customer service area, show the staffer what was missed, and get the coupon credited.

This is much ado about coupons, but I’ll offer two rationales. The first is obviously the cost savings. My online HEB account helpfully shows a running total of my coupon savings. For me, it’s several hundred dollars a year. But the other benefit is the sport of it. It makes the shopping chore a little more entertaining, at least for the (mildly) obsessed like me, to see how well I can do with them. On a good day, I may come home from the store and proudly tell my wife, “$28 in coupons today!” She just rolls her eyes.

For us retiree shoppers, there’s another factor often in play, as recently addressed in an article by Mark Crothers: absentmindedness. In that regard, habits can be very helpful crutches. For example, at our HEB, with its enormous parking lot, I always try to park in the same spot or very close by. My spot is far enough away that it’s usually vacant, and well, we’re all supposed to walk more anyway, right? But the payoff is I avoid that dreaded old guy phenomenon of wheeling the loaded cart out only to have forgotten where I’ve parked!

Once home, if there were HSA eligible purchases (QMEs) made, I mark them on the receipt and file it in my wife’s or my QME file, as appropriate.

Finally, and maybe this is where the “mildly” qualifier should in fact be deleted, I have one more habit my wife finds amusing. I tend to be a rather heavy emailer. I’ll write to a newspaper columnist, for instance, to compliment them on an article, or even to point out a mistake (which I’m sure they love). So when I find a grocery store item to be particularly good or bad, I’ll often email the manufacturer with my comments. While I enjoy the exercise itself, there is (of course, my wife would say), often a collateral benefit. They almost always respond, and will often include very generous coupons.

So, there you have it, a brief (oh yes, there’s actually more) description of my grocery shopping habits. If any fellow HDers are still awake after slogging through this and have their own methods and tips to add, I’d love to read them.

 

 

 

 

 

 

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Jerry Pinkard
10 hours ago

I have done most of grocery shopping for us for many years. I am not a coupon guy but I look for BOGO items that we use. Also, shop mostly on senior day which saves 5% and I have an AMEX CC which gives me another 6% savings. Sometimes, our main store will offer $5 off of a $70 order or something like that. I always try to get those.

OTOH, our daughter is a coupon person. I used to save our coupon sections of newspaper for her and she would clip them whenever she visited. She said she sometimes gets things free because of her coupons. Nowadays, coupons are online so I do not have to bother saving them.

I went to grocery store this morning. My bill was $75.30 and I saved $36.45. That is without the 6% AMEX credit I will get later.

One thing poster did not mention is food waste which can be a big deal. That may not be as relevant to a family of 6 but it is relevant to a family of 2 or 1. I have learned not to buy certain things because I wind up throwing most of it out. I love Costco but their huge food sizes do not work for us.

Last edited 7 hours ago by Jerry Pinkard
Ted Tompkins
1 day ago

Whew!!!!!!

baldscreen
1 day ago

I love this! Grocery shopping is definitely a good topic on HD. I try to buy things before we need them, like we had plenty of TP when there were shortages during Covid. LOL! Chris

R Quinn
1 day ago

“Mildly obsessed.” Give yourself more credit.

You missed a key point in this shopping journey do you return the shopping cart to where is belongs? 

Linda Grady
1 day ago
Reply to  R Quinn

😂😂😂 C’mon, we know the answer. And the stroll to the cart garage and back adds additional exercise. I also park in the outlying area of my grocery store lots. I alternate between two grocery stores: the one that’s a 10-minute drive and is never busy, plus is clean and provides a nice experience, and the other that is walking distance (I drive if it’s more than I can carry). This one is kind of dark and rundown, also rarely busy, but I feel it’s my duty through my patronage to keep the place open for the day when I may not be able to drive. I often see the same people at both places so I guess I’m not alone in this endeavor.

R Quinn
1 day ago
Reply to  Linda Grady

Even though I could be in mid-town Manhattan in about 30 minutes, I can’t walk to a supermarket, the closest is about two miles away.

PS yesterday I put three carts where they belonged because they were in the middle of parking spaces, one handicapped. I am admittedly obsessed with such inconsiderate, selfish, lazy behavior.

Linda Grady
8 hours ago
Reply to  R Quinn

You beat me: I only replaced my own cart yesterday at the walking distance supermarket. Remarkably, there were no carts standing idly in the lot.

Mark Crothers
1 day ago

I love this article—it’s perfect for Humble Dollar. Not only do I get to enjoy your humorous shopping odyssey, I also get to feel smugly superior about my own quirks, like whipping out a calculator to compare unit costs across different package sizes. But the real bonus? I spent a delightful hour this morning falling down a research rabbit hole about a successful grocery chain I’d never even heard of. Thanks for the entertainment and the education!

D.J.
1 day ago

The first order of business was to create a standardized grocery list which could be used each week and was easily modified. Importantly, it also needed to follow the geography of the store.” Wow. It’s a bit freaky how much we think alike! I created the same sort of list when COVID first hit and I wanted to get in and out of the store quickly. I still use it today.

Dan Smith
2 days ago

I learned coupon clipping from my dad, today I use digital ones. He was the guy that would travel from store to store for the best deals. I am not that guy. I sometimes drive Chrissy crazy with my search for deals, but my Kroger receipt tells me I saved $1400 last year. 
I like to try to plan meals according to what the  store has on sale each week. Buy one get one on chicken last week, $0.89 per pound spiral cut ham the week before, maybe a good roast this week. We also have good luck with most store brands. 
I could perhaps save more shopping at Aldi’s, many friends swear by it, but Chrissy doesn’t trust many of the no-name brands. Our loss I guess.

Bob Smith
22 hours ago
Reply to  Dan Smith

Never having clipped a coupon in my 80 yrs, recently the local Safeway here in Hilo HI offered the digital version, how cool is that? Shop and clip on my phone at my leasure.
I saved $17 my first 2 trips!
As for parking and carts. My wife and I park at the far corner of the lot, clear of swinging car doors and wayward carts. I generally find a cart on the way to the entrance for our use.
We still use Costco occasionally, if and when we’re ready for a 185 mile round-trip to Kona.
Aloha

Dan Smith
8 hours ago
Reply to  Bob Smith

Most people my age HATE the digital coupons, but I think they’re awesome and easy.

Bob Smith
19 hours ago

Before moving to Hawaii Is. 12 yrs ago , I lived to Orange Co. Ca, there were 4 Costcos within 20 minutes of home.

Dan Smith
8 hours ago

Andrew, here’s a good reason to give Trader Joe’s a try. Nice Greeting cards for a buck. TJ is an 80 mile round trip to Ann Arbor for us, and we find ourselves there several times a year for different reasons. I like to stop at TJ’s to stock up on those cards, as well as a few other things. I estimate the cards alone save us close to $100 dollars compared to other greeting cards.

OldITGuy
2 days ago

Good article. Very methodical process; impressive. My only comment for your consideration is that for the HSA expenses, rather than track individual expenses and receipts, I just use the Medicare part b premiums which gives me all the headroom I need to cover the amount I choose to withdraw each year from the HSA. Of course, both of us are over 65 so both our part B premiums qualify, which I believe wouldn’t be true if the owner of the HSA was under 65. Also, I don’t itemize my taxes so they’re not already claimed as a deduction. Gene

David Lancaster
2 days ago
Reply to  OldITGuy

Just a clarification. Only the Federal part B premiums and NOT supplement premiums can be paid for with one’s HSA funds.

mytimetotravel
1 day ago

That seems odd. What about Medicare Advantage premiums?

R Quinn
1 day ago
Reply to  mytimetotravel

You can use the HSA which seems strange given those is Part C still pay Part B premiums so in that sense Part C is no different than Medigap.

OldITGuy
1 day ago
Reply to  mytimetotravel

I agree; it is odd. It’s one of those quirks in the tax code that people can fall into by making logical assumptions. I already knew that, but frankly I just missed clarifying that supplement premiums don’t qualify. I’m really glad David pointed it out in his comment.

David Lancaster
1 day ago
Reply to  mytimetotravel

Don’t know about MA premiums as we have traditional.

OldITGuy
1 day ago

Yes, that’s what I meant but I failed to be sufficiently clear. Thanks for pointing that out so someone doesn’t misunderstand.

David Lancaster
1 day ago
Reply to  OldITGuy

When I speak to my wife about Medicare premiums I always use the terms Federal vs supplement premiums in order to be clear and concise. Here on HD I don’t want people making the mistake of thinking they can use their HSA funds for the supplement as I would figure if they were audited by the IRS it could potentially be a very expensive mistake.

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