The Discouraging Word is only updated once a month or so these days, but it’s worth visiting, because it provides some real lexicographical entertainment. The latest entry (Sommer prowde with Daffadillies dight, Posted Saturday, April 30, 2005—there are no permalinks) focuses on the word “dight,” which I knew as an archaic word for ‘adorn’; I probably once knew, but had forgotten, that it was from Latin dictāre ‘to dictate, order.’ What I did not know was how it had once flourished; the OED says “From the senses of literary dictation and composition in which it was originally used, this verb received in ME. an extraordinary sense-development, so as to be one of the most widely used words in the language.” As TDW says, there are 16 primary definitions, but I feel obliged to point out that that the last one shouldn’t be there (it’s “an erroneous use by Spenser,” F.Q. I. viii. 18 “With which his hideous club aloft he dights”—one of the odd Victorian features of the OED is its deferential inclusion of hapax mistakes by Great Writers, which have no more linguistic significance than similar errors made by the man on the Clapham omnibus); I also want to point out definition 4.b.:
To have to do with sexually. Obs.
c1386 CHAUCER Wife’s Prol. 398 Al my walkynge out by nyghte Was for tespye wenches Þat he dighte. Ibid. 767 Lete hir lecchour dighte hire al the nyght. c1386 __ Manciple’s T. 208. 1393 LANGL. P. Pl. C. II. 27 In hus dronke~nesse a day hus douhtres he [Lot] dighte And lay by hem boÞe.
It never ceases to amaze me how many improbable words have been pressed into service by the insatiable Anglophone appetite for sexual vocabulary.