[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.