It's really good advice if you're only doing this once per person, but you want to be a bit more careful that it doesn't lose its effectiveness if you want to b

It's really good advice if you're only doing this once per person, but you want to be a bit more careful that it doesn't lose its effectiveness if you want to be able to do it multiple times. Not sure if this happens for other people, but I know when I've gotten gifts based on my comments, I've sometimes started watching what I comment on with that person, which has affected my comments thereafter... not because the gifts turn out bad, but because there's frequently a non-financial reason I hadn't gotten those things myself earlier. e.g., maybe I feel it's just not worth anyone's money, I don't have room for it, maybe I feel it's a waste of resources, etc. So I feel like to make this work well you really have to know the person well to know why they haven't gotten the gift themselves already. One category of things where I think you can avoid the above problem easily (at least I have when I've tried it) is consumables, especially edibles. If you know your friend loves to eat something, then you can always buy them more of it; it's really hard to miss here. On the other hand, if you buy them something else, you might not know what the implications are. For example, if you know their computer is low on RAM and you buy them memory... you have no idea if they might've (say) only been putting it off because they plan to get a new computer anyway. Though, I guess is this easy to solve—just ask them on the spot why they haven't gotten that thing yet.