One from last week:
I have a co-worker who is often scraping by, barely able to make ends meet, who makes the worst financial decisions. Past gems have included: courtside seats at an NBA game last year for her wife's birthday (to make memories...sadly her wife has alzheimers so it's horrible but she's probably not going to remember it), maintaining two vehicles, both with bad gas mileage (and possibly payments still?) even though her wife will never drive again, getting so hammered out at bars that she got into a fight or got assaulted or something but wasn't sure about the details because she blacked out, two expensive, high maintenance dogs with "doggy day care" on a regular basis (even though there is someone home during the day, she sends the dogs to "doggy day care" often because "they like it"), etc. The latest? $3000 on front row seats to see Pink in concert, plus t-shirt (because what's a t-shirt on top of $3000 I suppose). It's so painful to watch because prior to the diagnosis her wife was the "responsible" one and would at least keep their finances in marginal shape. Now it's a total shit-show, but she's not particularly open to advice.