Found this one that checks all the boxes on r/boomerhumor.
Wow
Weirdest experience I ever had with this is with a customer at work.
It’s not an uncommon occurrence for men in their 40s and 50s to refer to their wives as “old bags”, so whenever I do the whole “Would you like a bag” spiel, there’s a 50/50 chance they will point to their wife and say “No thanks I have one right here” or say “Nah I left her at home” Or something else awful and then wink at me and call me darling or sweetheart and just make me want to be smited by god right in that second.
However there was one customer that came in and did this whole song and dance. Not out of the ordinary. What was, however, was how he then followed it up by going “I’m kidding, I’m divorced ha ha.” Then, his face drops and he turns to his friend with a look of absolute horror and goes “Wait, that’s probably why. Do you think that’s why she left me Andy? Because I said things like that?” And then proceeded to look like he was re-evaluating his whole life as his friend led him out of the store.
TL; DR = Boomers are weird and this one was given a glimpse behind the veil of self awareness in a Tesco Extra
