Inspired by this thread.
Box of condoms, suckers, My Little Pony.
Box of cheap wine, Ex-Lax, water balloons
A bottle of Ocean Spray Cran-Apple Juice, a can of Campbell’s Creamy Tomato soup, and the decapitated head of the produce manager on a pike.
What? Am I not playing the game right?
In b4 the link.
When I was in college band, we had a scavenger hunt of sorts where one of the items you had to bring in was a convenience store receipt with exactly three items on it: Condoms, vaseline, and bananas. Nobody quibbled when one of the hunters couldn’t find vaseline in the store, so bought KY jelly instead.
Ah, yes. We used to play this at Meijer, where you can buy literally anything, 24/7/364 (closed on Christmas). They even had a pet department, which made for some really interesting combinations, i.e., Vaseline/jumper cables/hamster, or boning knife/parakeet/box of Shake’n’Bake.
Me, I liked to go for the “huh?” We showed up after prom to pick up snacks for the ride to the amusement park the next day, so my purchases were Mountain Dew, Corn Nuts, and Snowballs, as well as a three-pack of dishtowels, some rubber bands, and a yam. And of course, I was in an evening gown at the time. I also tried to ride the mechanical pony at the front of the store - sidesaddle, of course - but they told me I was too heavy and shooed me off.
My son (2 1/2 yrs old) was playing grocery store in the kitchen. In his bag he chose the vaseline my wife uses as lip balm, and a bunch of bananas. Thankfully we keep the condoms upstairs.
Pack of Razor blades, bag of apples. On Halloween.
That isn’t bad at all IMO. I’m seeing a couple who want some alone time and don’t want another kid!
KY jelly, dog collar or leash, wine (If your supermarket sells it) 
You’re gonna get your dog drunk before you fuck him?
Well, my first thought upon seeing this thread was “A severed head, a hacksaw, and a bottle of chloroform.”
More in the spirit if the thread, a saw, a tarp, and bleach.
Census taker, fava beans, chianti.
Hacksaw, meat grinder, plunger.
Tarp, shovel, lye.
12 pack of cola/energy drinks, adult diapers, sunglasses.
Candles, wet wipes, tampons.
Plastic utensils, paper plates, enema kit.
I’ve many times found myself in a supermarket line late at night wondering what people must think of my purchases when seen without any context.
Recently the local supermarket had a terrific sale on 12 packs of soda (my one vice), but you could only get the sale price if you spent at least $10 on other items and you had to buy five 12 packs… which I didn’t know until I got up to the counter so I had to fill out my order but didn’t particularly need anything else. Ended up grabbing a box of condoms and a quart of my wife’s favorite ice cream.
I’m sure the cashier thought me a true casanova.
Dulcolax, a mirror and a turkey baster.
A shovel, cake mix, and rat poison.
Three bottles of liquor and a pack of baby diapers.
Have the cashier take back the diapers as you don’t have enough money.
Apparently no one here has ever worked as a cashier. Want to gross out the cashier? It’s hard to top the douche bag who pulls his bills from his sock after jogging.
I can think of several grosser places to extract a few bills from.
A hand mirror, scissors, and Preparation H.