One time my wife (girlfriend at the time) and I went to pick up some condoms and then we decided to also get some ice cream and the cashier (older lady) gave us like a 3 second look and I thought she was gonna say something but then I said, "the ice cream's for a friend" and it was the funniest thing I've ever said.
Wife still hasn't forgiven me. Cashier didn't say anything. My eyes were watering like crazy as I held in my giggles.
Haha, that's a good idea, the next time I make a dad joke I'll say, "oh no, was that a dad joke? You should probably take a pregnancy test, just in case it was."
One time I found a Jon Anderson record at a thrift store. The cashier picked it up, looked at it for 5 seconds, muttered "weird.", looked at it for 2 more seconds, and put it in the bag. Honestly I thought that was hilarious
I never feel awkward buying condoms. At the worst, it's a boast that imma get laid. At best it's normalizing safe sex for younger cashiers who may still be in that bareback or bust phase.
Now, enemas and lube? That's awkward, that's announcing to the world I'm a bottom. Lol
In this particular situation, one time without any thought, I grabbed a huge bottle of baby oil along, the cashier asked what I was using that for, I told her "for lotioning", thinking I made the worst decision, she replies back with "oh yeah I usually apply baby oil after showering".
To this day that bottle of baby oil still untouched sitting in my drawer.