After her husband passed unexpectedly, this woman received a pretty hefty life insurance payout. She chose to put $60k toward her daughter’s student loans, partly out of guilt. Years earlier, she had pressured her daughter into university before she was ready, which left her with a useless history degree, years of underemployment, and debt that literally doubled when she later went back for a law degree. To her mom, paying it off felt like correcting a mistake.

But her son, who never went to college, wasn’t too happy when he found out. He insisted she owed him the same in cash. She refused, saying the money wasn’t a prize; it was restitution.