99% of the time I've heard this argument, that dollar ends up going to neither.

Instead of trying to decide who is worthy of your dollar, perhaps consider what that dollar is worth to you vs. what it is worth to them.

If you give them a dollar and it's spent on something you don't approve of or you think they are not deserving that on them. If you don't give them anything because you assume they might not be worthy, that's on you.

A post on HN is an educational comment not passed on to an underprivileged child. A dollar spent a moderately expensive restaurant is a dollar not spent on rice and beans, with the surplus donated to charity.

If good deeds (or even neutral deeds) are scrutinized and discouraged, there will be no end of other, theoretical good deeds that might have been done, and no simple good deed will be done.

Well if one doesn't care if their donations are used for good purposes they can as well send them to me.

How do you determine which of the three men you pass on the street is a scammer, junkie, or hungry man? Maybe you give to a food pantry instead-- what about the people that use them for the free food but don't really need it?

How do you define scammer? If a person is homeless, but holds up a gas can with a sign that says "ran out of gas please help!" then they're lying about why they need the money, but they aren't scamming in terms of not actually being homeless.

What about junkies too-- they still need to eat. Absent enough money to do both, they might choose just to get high, deteriorate more, have even less chance of recovery.

There's no easy litmus test here. No easy way to ensure the money you give is going to be used in the best possible way to improve someone's life.

Scammers have better things going than sitting on street-corners begging for pocket change.

As for junkies - homeless junkies get hungry too.