A few years ago, I was in a writer’s group and we came up with this exercise for ourselves. We wrote down on slips of paper a bunch of objects that you can buy in a big grocery store, i.e., food, cosmetics, paper products, hardware, office supplies. Then each of us drew out five slips and our assignment for the next meeting was to write a short story (about 3-5 pages) with a narrative that explained the need for all of those items. It was really fun… smoked salmon, shampoo, diapers, a package of thumbtacks, and a layer cake. Or light bulbs, a hammer, vaseline, a dozen eggs, and a frozen pizza.
Years ago I was checking out at the local grocery and the checker noticed a package of economy Porterhouses I was buying. He looked at it when he picked it up and said, “nice meat, ma’am.”
It was such a strange thing to say, and my head is always in the gutter, but I wasn’t sure what to say to that, while I read his name tag that had the title “Front End Manager.”
I couldn’t help myself. I said, “Thanks! So… is there also a Back End Manager?” And giggled like I do.
No, no, the kind of dog you had was a “cheap date.” 
More than once I have found myself loading up a basket with other items I don’t really need, purely to dilute a potentially awkward checkout moment. Sad, I know.
Me and/or my Mother used to go buy around 30 bags of minced beef every week- (working at a zoo, it was convenient for small carnivores, of which we had many) and we’d take the opportunity to pick up other stuff at the same time- sometimes all the week’s shopping, sometimes just a bottle of milk or a bar of chocolate.
It was over 10 years of puzzled looks before one of the cashiers finally plucked up the guts to ask us why we were buying it, but by the next week, every single member of staff we spoke to was asking how the animals were doing 
Years ago I was with a bunch of guys buying food and snacks for a guys-hang-out day. The guy at whose house we were going to be suddenly remembered he needed toilet paper, so he grabbed a 12-pack and threw it in the cart.
When we were checking out, one of the guys leaned on the counter and casually asked the cashier, “In your professional opinion, is this the right amount of toilet paper for this much food?”
A while back I went to the movies with my brother. We went to buy snacks, and I said I wanted nachos. Bro said, “I’m not buying you nachos. Fake cheese is nasty.” I bickered back, “Fine! I’ll buy my own nachos!” The cashier, thinking that maybe we were a couple on a date, looked at my brother with a rather horrified expression that clearly said “how could you be so awful to her?!” then looked me square in the eye and asked, “Would you like some extra cheese on those nachos?” Yes, yes I would.
We still laugh about it.
A few decades ago I worked on the Anchorage International Airport flightline nightshift along with my then boyfriend. Often when we got off work, we’d stop by this little drug/convenience store that was open 24/7, to get some snacks.
The clerk was this old grumpy GRUMPY guy who was always there. No matter what we said, or how nice we were to him he never smiled or acted the least bit friendly. One morning in early November we got off work and stopped by, we got our usual hostess pies, and in addition I needed a couple more items, both household and some items for the upcoming holidays.
That morning was the first time we ever saw the cranky old dude smile. What was on the belt? A bottle of baby oil, a turkey baster and two hostess pies.
(Trying to erase from my mind the pictures in the old guy’s mind…)
If it helps, he wasn’t like ancient old, more like 50s old (which to us, as 20 somethings, was old).
I think the “official” name is Ice Pick.
That helps! 50?? Just a young whippersnapper. So he was having adolescent thoughts… ahhh!
Just for reference, this person is 50.
I once got to a grocery checkout with a bottle of champagne, a single wrapped rose and a box of condoms, which had absolutely nothing to do with each other or the evening’s plans. But it looked like…
I have to tell you that I’ve told your story to four different people so far, and they all laughed as much as I did. You’re spreading joy!
As is this person - Ming Na Wen - well, two months shy.
Yes, here too! Your story made a homebound elderly woman’s day a little brighter yesterday. I confess, I told it in first person, because it’s just funnier that way.