Kokora yo o kiku ga uchi ni mo kanashiki wa hito no namida mo tsuki ya shinuran - Gosen Wakashu(English Translation & Meaning)

ここら世を聞くが中にも悲しきは
人の涙も尽きやしぬらむ

Roma-ji: Kokora yo o kiku ga uchi ni mo kanashiki wa hito no namida mo tsuki ya shinuran
English Translation: Of the many deaths
that I have heard of in this world,
the saddest is this—
I wonder if your tears too
have not run dry at last
Meaning: Of all the many deaths I have heard of in this world, the saddest thing is this: I wonder whether even your tears have not run dry.
Commentary: Book Twenty Congratulatory Poems 1394

Headnote: "On offering condolences over the Fourth Princess."
Ise says that of all the deaths she has heard of, the saddest thing is that the mourners' tears may have run dry. Offering condolences on the death of the Fourth Princess, she feels it sadder than any she has known and imagines the bereaved weeping until their tears are spent.
According to the headnote, it was composed on offering condolences over the death of the Fourth Princess. The Fourth Princess seems to be Princess Kinshi, a daughter of Emperor Daigo who became the poet's wife. The next poem is the reply, and the two form an exchange.
The poet, Ise, was a daughter of Fujiwara no Tsugukage, Governor of Ise, and served Fujiwara no Onshi, consort of Emperor Uda. She received the emperor's favor and later bore Nakatsukasa to Prince Atsuyoshi. One of the Thirty-Six Poetic Immortals, she is represented in the Ogura Hyakunin Isshu by "Naniwagata mijikaki ashi no fushi no ma mo."

The first line, "Kokora yo o," means "of the many partings of this world."
The second line, "kiku ga uchi ni mo," means "among all I have heard," with the character for "within" read "uchi."
The third line, "kanashiki wa," means "what is saddest."
The fourth line, "hito no namida mo," means "the mourners' tears too."
The last line, "tsuki ya shinuran," means "may have run dry," with the interrogative binding particle "ya" closed by the attributive "ran." It pairs with "tsukisezarikeru" in the last line of the next poem.
Author: Ise
Source: Gosen Wakashu
Prev Poem: Musubiokishi tane naranedomo miru kara ni itodo shinobu no kusa o tsumu kana
Next Poem: Kiku hito mo aware chō naru wakare ni wa itodo namida zo tsukisezarikeru