Expressing sympathy or sorrow; related to or characterized by condolences or compassionate mourning.
From Latin 'condolatus,' past participle of 'condolere' (con- 'together' + dolere 'to grieve'), plus the English adjectival suffix '-ory.' The word evolved from formal expressions of grief at funerals to any sympathetic words.
The root 'dolere' also gave us 'dolor' and 'dolorous'—it's a Latin word so focused on suffering that it creates a whole family of 'sadness words' in English, all connected by shared Roman grief.
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