Myself and by DB are polar opposites I believe if you want something then you save he has always had the attitude of I deserve it regardless and is generally terrible with money etc.
He has 4DCs both him and my SIL work but would probably be lowish income family (but live rent free due to being left a house).
I've had 3 phone calls in as many weeks initially it starts asking how I am and how my pregnancy is going. As soon as I ask how things are there is a massive hint dropped so far it has been final reminder on electricity bill, the fridge broke and yesterday's call was my nephew managed to smash the TV at the weekend (kicked a ball).
He then says this is the last thing he needs before Xmas etc. I know he is hinting for me to offer the money (he knows I have a good job). So far I have avoided doing so by saying oh dear, have you tried free cycle/gumtree or speak to the company for a payment plan etc.
I could afford to sort it for him and part of me feels guilty as its also my nieces and nephews but I also know he has form. He would never pay me back and owes my parents in the region of 30k over the last 15 years from them bailing him out.
With a baby due in February and renovation work ongoing in our house I really don't want to offer it and my DH says not our problem that he's rubbish with money.
But my WWYD is in regard to the hints and do I just come out and say your just going to have to deal with it? We live 500 miles apart so thankfully it's only on the phone!
Sorry for the essay didn't want to drop feed.