Man wants to prevent roommate hitting rock bottom
Dear Worried: If your roommate brings an open bottle with him and drinks in public places (outside of licensed businesses), then he is breaking the law. New York City has an "open container" law, making this illegal. Bringing this up is a way in to talking to him about his drinking.
If he violates this law, "Charles" could face a serious fine, and/or be escorted to jail.
Your reluctance to talk about this openly means that he is not facing any natural consequences.
If you don't want to spend time out with him when he's drinking or drunk, you should say so. You say, "Whoa, how much have you had to drink today? You are too wasted for me to hang out with."
You can also say, "You have a drinking problem. I'm worried about you."
If he denies that he is drunk, or is forgetting his drunken behavior the next day, you might consider shooting video of him when he is drunk and sharing it with him when he is sober.
If he isn't paying his rent, then he actually cannot afford booze, and he'll have to move out. That is a straight-line consequence.
Please keep in mind that his drinking is not your problem to solve. Protecting him from his own rock bottom is a nice and generous thought, but you can't do it for him.
Tell him you care about him, that you are worried about him and that his drinking is affecting your relationship. Urge him to face this, and to get help if he needs it.
Dear Amy: My 32-year-old daughter is a single mother to my 18-month-old granddaughter.
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