Heart rending

Near-synonyms: heartbreaking, heartwrenching

[T]he old man, who appeared to be an ardent fisherman, told me of the large trout he caught in the neighbourhood thirty years ago, when he came here from Gudbrandsdale, and made the most heartrending complaints of the decrease of fish and increase of saw-dust, just as Sir Humphry Davy makes in his Salmonia.

It wavered an instant—then there was a heartrending crash—and the canary-coloured cart, their pride and their joy, lay on its side in the ditch, an irredeemable wreck.

I am suddenly assaulted by the most heartrending puppy-dog eyes I've ever seen as Emi pouts.

Oh, Marilla, it was heartrending. Mr. Phillips made such a beautiful farewell speech beginning, ‘The time has come for us to part.’ It was very affecting. And he had tears in his eyes too, Marilla.

These walls, under close examination, reveal messages carved in desperation by long ago victims. “If I must die, I beg it be done quickly,” reads one heartrending scrawl, signed by a man known only as Anthony.