When is the best time to tell someone you love that they may have an mental illness and may need help.
I wouldn't tell them that you think they're mentally ill, as it probably wouldn't be helpful. Leave that to a professional. The best thing you can do is offer to listen and empathize, and, if they are willing to help themselves, suggest counseling. Perhaps you can offer to go with them, or if they feel better doing it alone, offer emotional and/or financial support toward that effort. Good luck.
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casey