[temp8675309]

My mother in law just lost her job as a school librarian at the same time as my father in law is getting dicked around by workman's comp for an on-the-job injury. They need financial help but are too proud to take it - they don't like the thought of their son in law bailing them out even though I make far more than they do. This bothers me.

[r00fus]

There are several options here - their pride and wariness are probably natural human responses.

1) Pose the financial assistance as a loan or other arrangement that has reasonable terms.

2) Claim you're investing money with them or trust them (if they are savvy) to invest it for you. My sister did this for my parents a while back - she claimed that she was giving money for my father to invest, and I'm sure she's never expecting the money back.

There are numerous ways in which you can "ask them to help you" while in reality you are helping them. This can also bring you closer, but it requires a good deal of time and energy to set up (not to mention the money).

Keep in mind, this kind of arrangement is fraught with downsides too - there is a reason most folks recommend against loaning to, or going in business with your family.

[freshfey]

I'm sorry to hear that. What about taking care of "smaller" bills, like grocery etc. Make a list of what they need and just buy it (without asking them). Brush it off as "you were buying groceries anyway".

[tstegart]

Maybe your wife can approach them instead of you?

[wwwtyro]

Is it feasible to pay their debts/bills anonymously? I am also curious about this, for similar reasons.