Got a cousin (once removed), who frequently gets into debt with the expectation that my mum or me will bail him out.
If we don't bail him out immediately we're threatened with the interest payments
Buys a camera for his photography course. Breaks it the next day by having it fall off his mobile doll while it is in the air (I refuse to use the d-word)
We give him 2000$ to see a psychiatrist, then expressly tell him not to leave Sydney. The next day he is asking for money for a plane home from northern Queensland. Originally my mum was going to get reimbursed by my C3-PO uncle, but that was provided that my cousin actually spent the money on what he promised to spend the money on.