| What is she spending her money on? Is she into drugs or something? I'd say if it's something she needs counseling or help of that sort with, talk to her and tell her you're willing to emotionally support her as she gets counseling or something but tell her as a single mom that you've got a responsibility to financially support your family and you can't afford to bail her out anymore without your family suffering from it.
If she's a friend, she'll understand, if she's not, she shouldn't be asking you for money anyway. I'd say have a talk with her first and see if that stops it before you go talk to the boss.
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