<prompt> Human: My parents are separated. My father and step mother will have no troubles and will likely retire early even. My mother and stepfather on the other hand... Ive never heard any specifics about their finances, and just had assumptions. This year Ive heard some details and have concerns. My step dad is in the medical field, my mother has not worked for 15 or so years. They have for certain in the past pawned things or taken payday loans. Theyve had some medical problems in the past, but this year was an added kicker. My step dad got injured and was off of work for 7 months. He had half pay for a period of time and long term disability. Add in medical expenses for the year covered significantly by insurance, but likely a major factor still and being temporarily dropped from insurance and added medical issues for my mother and I cant imagine finances look very good. I know pretty obviously they dont have an emergency fund because of comments about not being able to afford interim medical expenses he didnt keep up with his insulin prescriptions to the point of nearly going to the ER! and have to assume theres not a lot going on for retirement funds or other assets. They of course didnt tell me any of this as it happened so couldnt help at all during. But how would I approach trying to help them sort finances for the future while theres still time? They wouldnt otherwise retire for at least 10 years. From many signs I handle money better than them, but would have less experience, so may have a discounted opinion in their mind. Id like to if possible, approach this sooner rather than having to make a much harder decision about helping them later. I wouldnt want to insult them by saying it, but Im concerned that they arent in a stable place and would need help, though I dont expect them to be forthcoming in asking for it.  <response>: Pawning and payday loans are last-resort, desperation moves. Huge red flags.Unless you have siblings this problem is going to land squarely on your doorstep in ten years or so. Avoiding that outcome means you have to take the initiative to break your familys money taboo, and ask respectfully for a full picture of your mom stepfathers finances.You dont have to frame it in selfish terms -- more like concerned loyal son daughter. I read all the time about people not saving enough for retirement, and I sure want you two to be okay. Whos your financial planner? Chances are they dont have one, so you can offer to set up an appointment with a fee-for-service fiduciary financial advisor who can review their picture.But essentially you want to know their income, net worth, investments and what they are, property value, life insurance, plans for long-term care and Medicare supplemental pharma etc., expected Social Security income, and so on. If they are deficient or thinking magically, as many older people do, at least they have a few years to correct things.Be prepared for resistance, or for them to act insulted. But its better to punch through now than to find them destitute and moving in with you in 10 or 12 years because this conversation was never held. 