I think the key is to make sure you generate love and freedom in letting them go. There may be pain, but you want the best for both them and you.
For instance, in a relationship, you might say, "I love you, and both you and I know that this isn't the best relationship for either of us. I would like for us to break up the romantic part now, while we can do it with lots of love for each other. It will be painful, but you know that if we wait, it'll just be harder later, right? Let's split now so we have love to take with us next time we try, rather than resentment. What do you think?" And then really listen to what the other person says.
In the case of the drug user, it is an act of love for both parties for you to say, "Look, drugs are something that I don't want to have around me. I can see the destructive power they have over people, and I won't tolerate that in my own life, and it causes me pain to see you give away your own power by getting high all the time. Much as I adore you, I'm going to have to remove myself from this lifestyle and situation. I love you and I trust that you'll do the right thing for yourself and your life." In this case, I would NOT put so much value in listening to what he has to say, because it will probably be the drugs talking -- manipulative, panicky, pleading. That's a good time to say goodbye.
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