My DH had a female family friend ( F1) who was close to DH father who died. FIL asked DH to look after F1. Her mental health wasn't great (she took drugs regularly)+she ended up taking advantage of us, pushing boundaries+then verbally insulting us when we tried to set boundaries so we ended the relationship. She has a friend F2 who kept contact with us. I didnt allow the falling out with the other woman to influence this friendship but was aware F1 was bad mouthing us. I was warey of course. F2 In time the friend cried poverty+suicide if she didn't get a car she couldn't work etc. We helped her out with a car. Shortly afterwards we didn't hear from her again. Drew a line. But she has an adult daughter she emotionally abandoned last year+who turned to us. We are fond of her as are our children. She started university 2 years ago+as DH has known her since she was born he wanted to gift her some money (her mum, F2 cried her poverty). Inhad no idea but until today but DH gave her the same amount last September. Today the daughter asked if we can give her her money early so she has spending money for her holiday at the end of the month. A 5* luxury spa holiday in the med, something we can only dream of being a family of 7. Do I confront her? I am feeling hurt+as she has made up with her mother now F2, am I being cynical? Sorry for the dump+thanks for reading.