heartbreaking

heart +‎ breaking

heartbreaking (comparative more heartbreaking, superlative most heartbreaking)

1. That causes great grief, anguish or distress.
   • 1941 April, “Notes and News: Railwaymen and Snow”, in Railway Magazine, page 177:

     Things went well with the clearing on Friday, but by Saturday, February 3, a 70 m.p.h. blizzard set in, and against such heartbreaking conditions, although an effort was made with the plough to keep open the sections cleared on the previous day, ground was gradually lost, [...].

• heartbreakingly
• heartbreakingness (uncommon)

heartbreaking (plural heartbreakings)

1. The breaking of a heart; great grief, anguish or distress.
   • 1999, Karen Gayton Swisher, John Tippeconnic, Next Steps: Research and Practice to Advance Indian Education, page 17:

     One could argue that Eliot's "great heartbreakings" were the overt physical signs of the inner psychological transformations achieved through brainwashing, cultural attack, and epidemic mortality.

• break someone's heart
• heartbreaker