There’s a restaurant near me that occasionally runs a special selling corn dogs two for a dollar. I’ve often wanted to go in and order a couple hundred of them and a large diet coke. spicy mustard on the side please.
K-Y jelly, “Beginner’s Guide to Spelunking” book, GI Joe scuba diver.
Bags of candy, children’s toys, condoms, sleeping pills and duct tape might raise some eyebrows. Especially if you drive a scuzzy white fan.
When I was in college, the town I lived in had laws forbidding the sale of non-food items on Sunday - because they weren’t “necessities”. We kind of liked to torture the cashiers over this - I had a friend who would try to buy tampons just so she could engage the cashier in conversation over why this purchase really was a necessity.
I would do stuff like hit the kids toy section and try to purchase “My First Book About Jesus” or other religious themed toys. Then try to engage the cashier in a philosophical discussion over why she wouldn’t sell it to me because God.
This started when we witnessed a cashier refuse to sell a can of Play-Doh. A mother was shopping with her child, she had the cart full of groceries and the kid was in the seat at the top of the cart, holding the Play-Doh can with delighted anticipation. The kid didn’t want to give it up and went into a full crying screaming meltdown after it was forcibly taken from him. We congratulated the cashier for doing the Lord’s work.
Yeah, we were kind of being dicks, because the cashier was doing the “right” thing in the eyes of the law. But this was in the pre-computer era, so it wasn’t like the registers were programmed not to ring non-food items or to track purchases. And we sometimes got the stuff. One of the cashiers rang up one of the religious toys once without any hesitation - probably because she knew we were playing with her and making us actually spend money on that stupid thing was probably the most vengeful response
I go and buy stuff for the concession stand all the time. We have a vendor but sometimes the orders are timely in getting to us. Tortilla chips, 25 or 30 bags. Canned drinks, cases and cases. Pickles in gallon jars. I got questioned alot at first, they all know me now.
Personally if I see something on clearance I like, I will buy 10 of them.
VagiClean.
In my first job, I was the market researcher on a brand of underarm deodorant. We were going to conduct a research study on potential new scents for our brand. The methodology featured little jars with samples of our prototypes, and other jars with samples of the leading competitors’ products – respondents would take a jar, uncap it, sniff the product sample, and rate it.
In order to conduct this research, we needed about 10 sticks each of several specific fragrances of different competitors’ deodorants. I went to Phar-Mor (a now-defunct drugstore chain), since they tended to stock large quantities. Thus, I was in line at the cash register, with about 40 sticks of deodorant.
As I waited in line to check out, a woman got in line behind me. She couldn’t help but notice the contents of my shopping cart. I turned around, and said, in a stage whisper, “I really sweat a lot.” 
A cake with “[your name] and [name of cashier] forever” printed on it and some paracord?
The canonical answer is: a pregnancy test and a single wire coathanger.
4 fried chickens and a Coke.
What Dirty Dancing style town is this so that I can avoid it?
One time at K-Mart I purchased only a box of Cheerios and a bottle of windshield wiper fluid.
One Halloween night, I had to buy apples. So just for fun, as I got to front of the line, I tossed a pack of good ol’ Gilette double-sided razor blades on top of the apples. Checker rang them up, “$7.22, paper or plastic?”
I thought, “Well, darn, this is no fun.” So as I paid I asked “Just wondering if you noticed…” and the clerk covered her mouth and started screaming while laughing. The other checkers, obviously her high school friends, starting laughing, too, mostly at her.
Part of your balanced breakfast!
I’ve purchased film, condoms, 25 cans of whipped cream, and lotion all at one time. All for different reasons, but it was pretty funny to see the cashier. She actually asked “What are you doing with all that whipped cream?” and my friend answered “Prank phone calls” and then we walked out. Laughed about it for a while after that.
Any set of items that total 6.66 (in any currency).
At an Albertson’s supermarket, long ago, I once had to replace an awful lot of dietary supplements. There was a sale on many of them, and I took advantage of the sale prices. It came out to a significant amount of money, and a large number of pill bottles (maybe 75 or so).
This was on Halloween. The supplements were the only things I bought. A manager indeed asked me the reason for purchasing so much of the stuff. He accepted my explanation.
This was about the time all the hospitals and the airport started allowing people to use their X-ray machines to vet the kids’ loot.
The best real-life combo I ever saw was a 40-ounce beer, condoms, and a pack of cigarets.
That was ME!
A couple of years ago I was at the Costco on the Saturday before the Super Bowl. I saw a guy pushing a flat out of the store with a 65" tv and a bottle of Wild Turkey.
I figured that guy had his weekend well planned.
I’ve had a couple purchase a pregnancy test, Plan B, condoms, lube, and a vibrator all in one go.
When I first started cashiering I went :dubious: at the combined purchase of baby stuff and beer, but now I’m sort of surprised when I don’t see that combo - apparently, a lot of new parents drink a lot of alcohol. At least in my neighborhood.
At this point, it would probably be pretty hard to make me uncomfortable. I’ve seen a lot of weird combinations.
They sell vibrators at a grocery store?