heartrending

adjective2

1. •
   That causes great grief, anguish or distress.

   • 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. — 1908
2. •
   That elicits deep sympathy.

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