Hello Mylaur,

I am new to studying Stoicism, and I too had similar thoughts recently. I did some searching on Reddit and people's past statements. I think it's worth starting by saying that you don't need to adopt all aspects of Stoicism if they go against values that you hold intrinsically. I have also found that different people give different descriptions of how to behave regarding the loss of loved ones. Epictetus' writings come off as very blunt, arguing that you should prepare yourself to feel the way about the loss of one's own loved one as one would in hearing about the loss of a friend's loved one.

11 - Never say of anything, "I have lost it"; but, "I have returned it." Is your child dead? It is returned. Is your wife dead? She is returned. Is your estate taken away? Well, and is not that likewise returned? "But he who took it away is a bad man." What difference is it to you who the giver assigns to take it back? While he gives it to you to possess, take care of it; but don't view it as your own, just as travelers view a hotel.

26 - The will of nature may be learned from those things in which we don't distinguish from each other. For example, when our neighbor's boy breaks a cup, or the like, we are presently ready to say, "These things will happen." Be assured, then, that when your own cup likewise is broken, you ought to be affected just as when another's cup was broken. Apply this in like manner to greater things. Is the child or wife of another dead? There is no one who would not say, "This is a human accident." but if anyone's own child happens to die, it is presently, "Alas I how wretched am I!" But it should be remembered how we are affected in hearing the same thing concerning others.

~ Enchiridion

While I think there are good things to take away from this, I find that I personally associate more with Seneca's approach to loss and grief, as described in one of his letters to Lucilius:

Moral letters to Lucilius - Letter 99

Notable quotes:

Regarding the problem with excess grief:

Grief like yours has this among other evils: it is not only useless, but thankless. Has it then all been for nothing that you have had such a friend? During so many years, amid such close associations, after such intimate communion of personal interests, has nothing been accomplished? Do you bury friendship along with a friend? And why lament having lost him, if it be of no avail to have possessed him? Believe me, a great part of those we have loved, though chance has removed their persons, still abides with us. The past is ours, and there is nothing more secure for us than that which has been.

and then, regarding the appropriate amount of grief:

15 - And what, then? Now, at this time, am I advising you to be hard-hearted, desiring you to keep your countenance unmoved at the very funeral ceremony, and not allowing your soul even to feel the pinch of pain? By no means. That would mean lack of feeling rather than virtue – to behold the burial ceremonies of those near and dear to you with the same expression as you beheld their living forms, and to show no emotion over the first bereavement in your family. But suppose that I forbade you to show emotion; there are certain feelings which claim their own rights. Tears fall, no matter how we try to check them, and by being shed they ease the soul. 16. What, then, shall we do? Let us allow them to fall, but let us not command them do so; let us weep according as emotion floods our eyes, but not as much as mere imitation shall demand. Let us, indeed, add nothing to natural grief, nor augment it by following the example of others.

and, finally, regarding how a Stoic recalls a loss:

You may, however, speak often concerning the departed, and cherish his memory to the extent of your power. This memory will return to you all the more often if you welcome its coming without bitterness; for no man enjoys converse with one who is sorrowful, much less with sorrow itself. And whatever words, whatever jests of his, no matter how much of a child he was, may have given you pleasure to hear – these I would have you recall again and again; assure yourself confidently that he might have fulfilled the hopes which you, his father, had entertained. 24. Indeed, to forget the beloved dead, to bury their memory along with their bodies, to bewail them bounteously and afterwards think of them but scantily – this is the mark of a soul below that of man.

In the above, at least in my interpretation, you are encouraged to feel the sadness that is appropriate for the situations. However, you are still encouraged to be ready to acknowledge the impending nature of mortality for all things, and the ability to accept that we may sometimes be inclined to feel that someone passed "before their time". He also notably discourages excessive lamentation, and encourages one to try to be strong in dealing with these losses.

Personally, I think that Stoicism is not mutually exclusive with feeling significant love and affection towards others. However, now, I do not shy away or push morbid thoughts out of my mind. When I am feeling love and happiness about someone, I will sometimes reflexively feel a fear that I could lose this someday. Whereas I would ignore this in the past, I now use it as an opportunity to face that possibility head-on and recognize the importance of being comfortable with the possibility that I or my loved ones may pass away at any time.