Entry 2 senses Webster, 1913 Dreary /(drēr"y̆)/ · Drear·y · IPA /ˈdɹɪəɹi/ 01 a. Sorrowful; distressful. 1. Sorrowful; distressful.[Obs.] 2. Exciting cheerless sensations, feelings, or associations; comfortless; dismal; gloomy. “Full many a dreary anxious hour.” — Keble. “Johnson entered on his vocation in the most dreary part of that dreary interval which separated two ages of prosperity.” — Macaulay.