heartrending

That causes great grief, anguish or distress.

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.

That elicits deep sympathy.

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.