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It has become customary to sing יָמִים עַל יְמֵי מֶלֶךְ תּוֹסִיף שְׁנוֹתָיו כְּמוֹ דֹר וָדֹר in honour of the senior Rabbinic speaker at a function.

An explanation is given here.

The Pashut explanation given by Rashi on this passuk is that Dovid Hamelech is asking Hashem that even if it has been decreed that he die young at the hand of his enemies, Hashem should remove that decree and grant him the full 70 years of every generation.

I feel that it must be very worrying for the person for whom it is being sung because it may indicate that he needs to have his days lengthened and remind him of his mortality.

Is it a good thing to sing?

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Every day you are supposed to remember the (Yom Hamisa) day of death. –  Gershon Gold Feb 2 at 15:59
@GershonGold "To remember" yes; to be reminded - that's my question. –  Avrohom Yitzchok Feb 2 at 16:08
Why don't you ask whoever you want to sing it to if they are offended? I don't know why there should be a general rule. –  Double AA Feb 2 at 18:14
I don't think most people are thinking they are immortal until you remind them they aren't. You wouldn't refrain from telling someone "refuah sh'leima" because it reminds them that they get sick. It is wishing them well despite their mortality. –  YEZ Feb 3 at 0:24
Many songs take words out of the original context and meaning. איש את רעיהו יעזורו is one of the famous ones. –  Shmuel Brin Feb 3 at 0:43
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