You have been watching them circle the same problem for months, maybe longer. You have suggested resources they never used, cleared space in your own life to hold space in theirs, made calls on their behalf. They say thank you and then do the thing you asked them not to do again. You do not know if you are being patient or complicit. You do not know if your continued presence is an act of love or an act of fear.
The question underneath the question is harder than it looks. It asks you to separate care from control, patience from avoidance, love from the need to feel useful. Three thinkers on the Consilium roster would come at this from entirely different angles, and they would not agree with each other.
Rogers: the help that blocks change
Carl Rogers built an entire theory of human change on one observation: people do not change when they are pushed. They change when they feel genuinely accepted as they are. Unconditional positive regard does not mean unconditional approval of every behavior. Rogers was precise about this. You can accept a person fully while being honest about what their behavior costs them and others. But the acceptance has to be real, not a strategy for moving them toward where you think they should go.
The curious paradox is that when I accept myself just as I am, then I can change.
Rogers would apply this to the person you are trying to help. Your repeated offers of assistance may be communicating something you have never said aloud: that you cannot accept them as they currently are. The help arrives with a message attached. That message is the problem, not the help itself. Their resistance to your offers is not stubbornness. It may be a response to being treated as a project rather than a person. If that is what is happening, different help will not fix it.
Havel: enabling is living within the lie
Vaclav Havel's argument in The Power of the Powerless is about political complicity, but the logic scales down. Living within a lie, he argues, requires the participation of many people performing small acts of pretense. A system of dishonesty does not sustain itself. It needs individuals who keep acting as if things are normal, who absorb the cost of the fiction and keep it running.
Living in truth...is both an act of resistance and an affirmation of responsibility.
Enabling someone who will not help themselves is this pattern made personal. Every time you absorb the consequences of their choices, you signal that the current situation is survivable, that the fiction can continue. Havel would not frame refusing to enable as harshness. He would frame it as honesty. To truly help someone may mean refusing to pretend that what is happening is acceptable, even when that refusal costs the relationship. Absorbing the cost yourself, quietly and indefinitely, is not love. It is a form of participation in a lie that serves neither of you.
Weil: are you paying attention?
Simone Weil would not start with whether to help or not help. She would start with whether you are paying attention. Her argument in Waiting for God is that genuine attention is the rarest form of generosity, and most of what we call helping is not attention at all. It is projection. We see someone in distress and we respond to our own discomfort at witnessing it, not to what the person actually needs.
The capacity to give one's attention to a sufferer is a very rare and difficult thing; it is almost a miracle; it is a miracle.
The help you are offering may be the help you can give, or the help that makes you feel useful, or the help you would want if your positions were reversed. That is not nothing. But it is not the same as actually seeing this specific person in this specific situation. Weil would not tell you to stay or go. She would ask you to look harder first. Is your help addressed to them, or to your own need to do something with the discomfort of watching someone you care about refuse to change?
Where they disagree
Rogers points toward acceptance. Not acceptance of the behavior, but acceptance of the person as they are right now. He would say your help is being received as a message of non-acceptance, and that is why it is not working. The answer is not different help. It is a different quality of presence.
Havel points toward honest confrontation. He would say that absorbing the consequences of someone else's choices, however quietly and lovingly, is a form of participation in a fiction. Real responsibility means refusing to pretend, even when pretending is the easier path.
Weil says both of you need to actually look before you can know which of those is called for. She would not grant that you have seen this person clearly enough yet to know what they need. The question she puts to you is not what to do. It is whether you have been paying real attention, or performing it.
Where all three converge is uncomfortable. Rogers would say your help may serve your need to not accept them as they are. Havel would say your patience may serve your need to avoid an honest confrontation. Weil would say your offers may serve your need to feel like you are doing something. All three are asking the same question from different angles: are you helping for them, or for yourself?
The question you came here to avoid
The question in the title points outward: when is it right to help someone who will not help themselves? But the harder version points inward. You are not only asking what the right thing to do is. You are asking what it says about you if you stop. And underneath that is a question you have not quite let yourself ask directly: whether your continued presence in this situation is still about them at all.
You came here looking for a rule that would settle it. There is no rule. There is only the question Rogers, Havel, and Weil each arrive at, coming from completely different directions: is this about them, or about you?