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The Collaborative International Dictionary of English v.0.48:

Silly \Sil"ly\, a. [Compar. Sillier; superl. Silliest.] [OE. seely, sely, AS. s?lig, ges?lig, happy, good, fr. s?l, s?l, good, happy, s?l good fortune, happines; akin to OS. s[=a]lig, a, good, happy, D. zalig blessed, G. selig, OHG. s[=a]l[imac]g, Icel. s?l, Sw. s[aum]ll, Dan. salig, Goth. s?ls good, kind, and perh. also to L. sollus whole, entire, Gr. ???, Skr. sarva. Cf. Seel, n.] 1. Happy; fortunate; blessed. [Obs.] --Chaucer. [1913 Webster] 2. Harmless; innocent; inoffensive. [Obs.] "This silly, innocent Custance." --Chaucer. [1913 Webster] The silly virgin strove him to withstand. --Spenser. [1913 Webster] A silly, innocent hare murdered of a dog. --Robynson (More's Utopia). [1913 Webster] 3. Weak; helpless; frail. [Obs.] [1913 Webster] After long storms . . . With which my silly bark was tossed sore. --Spenser. [1913 Webster] The silly buckets on the deck. --Coleridge. [1913 Webster] 4. Rustic; plain; simple; humble. [Obs.] [1913 Webster] A fourth man, in a sillyhabit. --Shak. [1913 Webster] All that did their silly thoughts so busy keep. --Milton. [1913 Webster] 5. Weak in intellect; destitute of ordinary strength of mind; foolish; witless; simple; as, a silly woman. [1913 Webster] 6. Proceeding from want of understanding or common judgment; characterized by weakness or folly; unwise; absurd; stupid; as, silly conduct; a silly question. [1913 Webster] Syn: Simple; brainless; witless; shallow; foolish; unwise; indiscreet. See Simple. [1913 Webster]