"Whoever sings songs to a heavy heart is like one who takes off a garment on a cold day, and like vinegar on soda." (Prov. 25:20)
It is often said that "laughter is the best medicine." I don't necessarily disagree with that. When a person has a bad day, it always helps to lighten the mood and laugh a little. But I don't think Solomon is talking about a person who just has a bad day and needs their spirits lifted.
When a person has a heavy heart, when they have experienced hardship or tragedy in their life, the last thing they need is for someone to make light of it; the last thing they need is for someone to come and try to cheer them up. That may work for a bad day, but it doesn't work for a heavy heart.
Matthew Henry explains it best when he says, "The absurdity here censured is singing songs to a heavy heart. Those that are in great sorrow are to be comforted by sympathizing with them, condoling with them, and concurring in their lamentation. If we take that method, the moving of our lips may assuage their grief (Job 16:5); but we take a wrong course with them if we think to relieve them by being merry with them, and endeavouring to make them merry; for it adds to their grief to see their friends so little concerned for them; it puts them upon ripping up the causes of their grief, and aggravating them, and makes them harden themselves in sorrow against the assaults of mirth."
Solomon says in Ecclesiastes 7:2-3, "It is better to go to the house of mourning than to go to the house of feasting, for this is the end of all mankind, and the living will lay it to heart. Sorrow is better than laughter, for by sadness of face the heart is made glad." The wise man is not condemning laughter and joy; he is simply arguing that there is more benefit in mourning than in laughter. Mourning can make us wiser, it can cause us to more deeply appreciate life and God.
With this in mind, why would we want to "sing songs to a heavy heart?"
If someone is mourning or experiencing hardship, console them. Point them to God.
Grief is a natural part of life. The sooner we learn to deal with it the right way, the better!
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