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Seneca to Lucilius, 29: how to truly help a friend

Seneca and Lucilius shared a friend by the name of Marcellinus, who was going through a bit of a crisis at one point. Who has not been in a similar situation? What are you going to do to help your friend?
Seneca tells Lucilius that Marcellinus doesn’t visit often anymore, a sign of his detachment from his own friends. He is avoiding Seneca in particular because he knows that the philosopher will tell him the hard truth about his situation (about which we don’t actually have any specific detail, unfortunately), and Marcellinus is in no mood to hear the truth.
We see here how much more nuanced the Stoic take is even when compared to that of our close cousins, the Cynics. Seneca is careful, and understands that while Marcellinus needs help, he will not be receptive to a blunt approach, which would probably drive him into further isolation:
Truth should be told only to those who will listen. For that reason, people frequently express doubts about Diogenes and the other Cynics who employed wholesale freedom of speech and admonished everyone they encountered. (XXIX.1)
Nevertheless, if philosophy is to be useful, then this is precisely the sort of circumstances where the rubber hits the road, so to speak. Seneca is still optimistic that he can be of help to his friend, if he extends a hand immediately, but he is also aware that his is, in a sense, a dangerous mission: Marcellinus is strong in character and intellect, and it may be he go ends up dragging his rescuer down, rather than being helped by him.
This is something many of us can relate to. Really helping a friend is a delicate operation, in the course of which we need to steer clear of both the Scylla of being too blunt and thereby closing their mind and the Charybdis of not being sufficiently frank and end up giving vanilla advice that is useless in practice. Moreover, we need to be in a relatively good position ourselves, or we risk falling into the waters from which we were just now attempting to rescue our friend.
Interestingly, Seneca worries that Marcellinus will laugh at the whole notion that philosophy…