is what seems to work for me:
Discuss the entire thing with the family member as a loan. Then when you send the money, tell them to pay it back to the church or some other charitable cause you can agree on. That way you never have any visibility (and they know you won’t have visibility) into whether they actually pay it back and things are never awkward or cause hard feelings between you. The only condition is they never speak of it to anyone.
It’s effectively a gift from your end and a loan from their end.