What should we do with friends who constantly get themselves into difficult situations but are not open to being helped?

Lama Ole’s answer:

If someone really needs to hit his head against the wall, you shouldn’t always be there to hold up a pillow. Act like a bullfighter instead, who shouts “Olé” and lets the bull run into the wall! Before bad habits become too deeply rooted, people should quickly feel that the consequences really hurt—that they hurt so much that the ego can’t sugarcoat things anymore. Perhaps this way they’ll get the idea to change something.

Of course there are a few things that must not happen: for example, one must do everything possible to make sure a person doesn’t get or spread AIDS. We must not let anyone seriously harm the health of others, but it is completely OK for people to get a bloody nose on a personal level! Often it has to really hurt before the ego is ready to give up territory.

Buddha’s teachings are something very, very precious. One should not run after people with them! You let them know that you have the teachings, and they can run around until they discover that they need them. Then you can share what you have. But no one can expect you to run after them.