<prompt> Human: Some basic background: Im 26, just got out of school about two years ago, some savings, live well below my means, have a roommate, engineer at a start up firm, no debt, no flash other than a nice used car which I own outright, moved out at 16. Mother, 56: Lost a job 10 years ago and instead of trying again, just went on SSI and other programs. Got a diagnosis for fibromyalgia and just uses that as an excuse for anything she doesnt want to do. Hard to talk to because everything turns into a pity party. She inherited a house from her father which she lives in. She inherited about 15k from a relative about two years ago, and that money is apparent gone. She hadhas a lot of problems with buying useless things like gemstones. Now, she is saying she cannot live off of her benefits alone anymore and needs money from me. Apparently, she was borrowinggetting money from family friends but theyre getting reluctant now. I would like to help her, but I feel that Id just be enabling her to continue with this awful lifestyle. Is there a middle ground where I can give her money, but make it conditional that she do some volunteer work. Also, I dont want her to be dependent on my money. Im afraid if I did it once or twice, shed just start expecting a monthly check forever. Edit: Thank you, everyone, for your advice and personal anecdotes. I see clearly, now, that if I give in easily and give in to her demands Ill just be codependent and that I need her to lay bare her finances and budget before any further discussion.  <response>: No. Just no.By all means, help her work out her finances, but dont start paying her to not work. Dont pay her to volunteer, either. Dont give her money on conditions, period. When you do that, you create a dependency framework, where she can expect money from you indefinitely, provided she meets those conditions. Even if you say its one time only, or for six months only, in her mind its forever, because the time horizon only goes out until the next paycheck.Additionally, debt sours relationships. The more a family member owes you and is aware of it, the more they stop being a family member. No one has to steer things that way, it just happens. If it were a friend owing you, you would drift out of touch. When its a family member, the distance may last the rest of your life.Caveat: Im all for helping out family if it comes to an emergencylife event thats pulled the rug out from under them. Its the long-term leaching thats caused me problems. 