<prompt> Human: I apologize for how long this will be, so TLDR at the bottom. Someone close to me struggles financially. He is 23, he lives at home and works a hard labor job, so in summer makes roughly 2000-3000 a month, and in winter roughly 800-1200 a month. His family is not well off, and his mother struggles, so she expects him to pay 150-250 a week to her to help with bills. He doesnt own his car, she technically owns it, and claims that the money is for the car, but still wont let him take it when he wants to. He pays all the gas for it which is quite expensive due to his job. His sister does not pay anything at all. Because his mom takes so much money from him, he struggles. On top of this, he does drugs, but is currently trying to stop. I obviously know that that part of this story is completely his fault, and I encourage him to stop his drug use. Now for the harder part. He owes his bank 400 from overdrafting and god knows what else, and got speeding tickets last month, resulting in 300 in fines and 500 for a lawyer. He just paid for repairs on his car which was another 200. Every time he gets into rough spots which is regularly I end up sending him money. I sent him over 400 since August 15th, 60 of it just in fees for sending it over the internet. I told him to get a bank that accepts Venmo, but because he owes his current bank 400, he cant open another bank account. I cant afford to send him this type of money, I make less than he does a year. I feel trapped because I dont want him to ruin his future, so I feel like I have to send the money when he needs it. Like he had to spend 100 to plead not guilty so he didnt lose his license, and he didnt have the money and it was the last day to pay so I ended up sending it so he wouldnt lose his job. I cant afford this, its stressing me out and I shouldnt have to change my lifestyle to bail someone out regularly. He currently owes me almost 800. Any advice would be appreciated. TLDR: guy doesnt make a lot and his mom takes 1000 from him a month, he keeps getting into bad financial spots and I end up bailing him out. I cant afford it anymore, but dont want him to ruin his future.  <response>: You have to learn to say NO. Its hard, might ruin the relationship, but him borrowing money is already doing that anyway. 