April Masini, a relationship and etiquette expert, shared insights with The New York Times on how to express sympathy after someone’s loss. April Masini explains that meaningful condolences come from sincerity, empathy, and thoughtful presence rather than polished words or public gestures. Masini emphasizes the value of timely, personal messages, heartfelt remembrance, and authentic emotional support, while cautioning against clichés, self-focused comparisons, and performative sympathy. Her advice frames grief etiquette as an act of human connection, where compassion, respect, and emotional awareness matter more than finding the “perfect” words.