My friend and his wife just had another baby. My friend is in graduate school, has student loans, and is commuting 2 hours one way to his job in another city. His car recently passed away and he had to buy a new (used) car to get to his job. He told me he has started working night shifts at a convenience store doing food prep/etc. Their new baby was born premature and is very expensive. In addition the wife can’t work and she has burdensome student loan payments (private loans that can’t be deferred).
Meanwhile, my wife and I live below our means. I work constantly and make relatively a lot of money. We have no children for unknown reasons. We have no debt. Basically, we’re in a position to give my friend a substantial amount of money. We want to give them enough money to at least get out of the situation where he is working 2 jobs and going to school full time while they can barely afford rent/basics.
How can we give them money without making the relationship awkward? I don’t want him to feel “indebted” to me. I don’t want them to think my wife and I are rich or even think about us at all. I cannot figure out a good way to give the money anonymously without causing my friend undue suspicion. I don’t live close enough to this friend to drop off cash in the mailbox. I also don’t want it to “get out” that I’m in the habit of giving away tons of money because I don’t have enough to give a significant amount of money to every person who needs it. I just feel that this friend is the most in need. I don’t want to embarrass this person or wound their ego/pride. I don’t want them to be on the receiving end of “pity.” I just want to get the cash to him in the least offensive, most effective way possible. Thoughts? Has anyone ever received financial help from a friend? How can this be done without ruining the relationship?