Great thread.
I've shared these before, but here goes.
My dad is a serial CF. We just laugh about it now.
One year, he was house and dog sitting while I was on holiday in the states for two weeks, I left a full cupboard and freezer of food for him and enough dog food to last until way past when we got back. I obviously paid his travel costs to mine, bought him a souvenir abroad and duty free by way of thanks for his help.
A few days before we were due to come home, I got a panicked voicemail saying he'd ran out of dog food (ignored my instructions) and had spent the last of his money on dog food and had no money left for his own food. I couldn't understand how this was the case, there was enough food in my house to last him a month. Mortified, as the message was left the day before, I immediately wired him £30 and texted to say I'd call later.
I called him later, he explained he'd forgotten about my instructions about the dog food and yes he did have lots of food in for himself, but "as it was a Friday he wanted takeaway", but had no cash after buying the dog food. But "not to worry, I went to the kebab man and told him IchWill is my daughter, explained my predicament and asked if I could have kebab and chips, and that you'd settle up when you got back from holiday", the kebab bloody gave him it too.
I was so embarrassed. And we came home to two obese dogs.