classic waka stream

悲しさをこれよりけにや思はまし
かねてならはぬ別れなりせば
Roma-ji

Kanashisa o kore yori ke ni ya omowamashi kanete narawanu wakare nariseba

English Translation
Would I have felt
my sorrow still more deeply
than I do now,
had this been a parting
I had not grown used to before?
Meaning
Would I have felt my sorrow even more deeply than now, had this been a parting I had not grown used to beforehand?
Commentary
Book Nine Poems of Lament 580

Headnote: "Composed when someone offered condolences on the death of a boy I had been close to, who had unexpectedly grown distant from me before he died"
Composed when someone offered condolences on the death of a boy the poet had been close to, who had unexpectedly grown distant before he died. Had this been a parting I had not grown used to beforehand, would I have felt my grief even more deeply than now, he asks. Telling himself that, since they had grown apart in life, he should be somewhat accustomed to parting, he nevertheless lets a deep sorrow show through.
The author, "the Monk Jōgon," was a monk of the late Heian period, but little is known of his life.

First line, "kanashisa o": "the sorrow" of losing the boy.
Second line, "kore yori ke ni ya": "ke ni" means "all the more." The interrogative "ya" closes with the attributive "mashi" in the third line.
Third line, "omowamashi": the counterfactual "mashi," in concert with "seba" in the last line, "would I have felt it so?" The poem pauses here.
Fourth line, "kanete narawanu": "kanete" is "beforehand," and "narawa" the irrealis of "narau," "to grow used to," "not used to it beforehand," implying that the estrangement in life had accustomed him to parting.
Fifth line, "wakare nariseba": "se" is the irrealis of the past "ki," and with "ba" forms a hypothetical, "had it been a parting." It is a counterfactual answering "mashi" in the third line.
Author
Jōgon
Source
Senzai Wakashu
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