Fun Fact

Doleful perfectly captures that particular expression dogs make when they want something—those sad, pleading eyes that suggest profound suffering despite being perfectly fine. The word connects to “condolences” through shared Latin roots in grief and sorrow. Medieval writers loved doleful to describe tragic heroes, mournful songs, and sorrowful landscapes. While sadness has countless synonyms, doleful carries a theatrical quality that makes sorrow almost performative—it’s grief you can see and hear, whether in a hound’s whimper or a poet’s lament.