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Secrets of the Darth Vader Boyfriend
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jducoeur
h/t to metahacker, who happened to mention this excellent article in passing. It's not new, but I hadn't seen it before, and it is *well* worth reading if you have a friend whose choice of SO you disagree with. (Which, as far as I can tell, pretty much everybody has at one time or another.) The first half of the article describes how to recognize certain kinds of problems; the more important second half describes how you, as a friend, can be helpful. (Or at least, not harmful.)

It's fine advice, and generally how I try to handle such situations myself nowadays. But it took some serious missteps on my part to realize that this was the best way to approach such situations, so I commend this as guidance to help you avoid making similar mistakes...