Dad moved in 2 years ago. Mom died almost 3 years ago. She did all the finances for the house and business. I took over his finances then slowly turned it back to him (sink or swim). He finally was able to get a handle on things. Pay his insurance and car expenses and entertainment. The problem is he is about $200 short each month due to his now getting out and being social. He joined a church and now is going on weekly lunches. I want him to be social but every time I turn around he is going out to dinner and lunch. It is a double edge sword. I wanted him to be social it is good for all of us but at the end of the month he is coming to me for money. He was pretty good about paying me back. Its not that I don't have it but at the end of the year I get tight on money myself (I own my own business), Between him and my kids I cant afford the dollar and hundred (nickle and dime is no more). I pay all the house expenses food etc... He was like this with mom, he would over spend then she would call me crying and there was many times I fronted them money (not paid back much but that was OK). All he has is SSI which is enough to cover his insurance and regular expenses. My sibling covered his $6000 car repair last year and also covers his smart phone. I had to front the latest car repair. It is almost like he doesn't care and its fine to ask me for a couple hundred expecting me to have it in my pocket (OK I do but that is for me). Do I go over a budget with him and tell him he has only so much a month for entertainment? I did that when he moved in. Now it is dinners and lunches out (I am not talking fast food here). I can't track all his expenses online he has taken to using cash from the ATM ( I set him up online and have all access to his accounts). I don't want to stifle his activities lord knows I want him to get out of the house but it was like this with him all along trying to keep up with the Jones's. They would go on trips and cruises and vacations and live in huge houses and buy new cars lavish on the grandchildren all while declaring bankruptcy twice. This is the reason I don't spend lavishly and due in part to my wife who grew up in an immigrant household where money was to be saved. He is not aware that I watch his spending, he just got his check and he is a like a sailor on leave...... This is worse than having kids again!