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Discover Ludwig"make unhappy" is a correct and usable phrase in written English.
It is often used to express an action that causes someone to feel unhappy or sorrowful. For example, "His careless words made her feel very unhappy."
Exact(8)
Can Kim make unhappy schoolboys stand on their desks?
JOHN LANCHESTER: Daniel, I haven't seen figures, but I bet they make unhappy reading.
They all stay in the same hotel, where Rob and the husband make unhappy drinking partners.
Diffident artist Charles and callous rakehell Addington (who crosses the ocean with five cases of port and advanced syphilis) make unhappy travelling companions: "You, sir, are a milksop".
In her review in The New York Times Book Review, the Arab author Inea Bushnaq wrote of Mr. Aburish, "Some of the truths he reveals make unhappy reading, but ultimately it is his book's brusque frankness that gives it value".
There are pedantic quirks, including a brief discussion over the correct use of "whence", which make unhappy turns of phrase stand out all the more: "The list of signatories was long and staunch".
Similar(52)
We made people unhappy because we ourselves were made unhappy in irrevocable ways.
It must have made unhappy reading for him.
"He made unhappy arguments before the courts and the judges consistently rejected them.
Commuters no longer rode into the city only to be made unhappy in high offices.
"It is not a lack of love but a lack of friendship that makes unhappy marriages".
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Since I tried Ludwig back in 2017, I have been constantly using it in both editing and translation. Ever since, I suggest it to my translators at ProSciEditing.

Justyna Jupowicz-Kozak
CEO of Professional Science Editing for Scientists @ prosciediting.com