The earliest use is in West Germanic comparative forms introducing the second member, i.e. bigger than (compare Dutch dan, German denn), which suggests a semantic development from the demonstrative sense of then: A is bigger than B, evolving from A is bigger, then ("after that") B. Or the word may trace to Old English þonne "when, when as," such as "When as" B is big, A is more (so).
As a conjunction, "in that case, therefore," in Old English. As an adjective, "being at that time," from 1580s. As a noun from early 14c. For further sense development, see than. Similar evolutions in other Germanic languages; Dutch uses dan in both senses, but German has dann (adv.) "then," denn (conj.) "than." Now and then "at various times" is attested from 1550s; earlier then and then (c. 1200).
late 14c., originally in grammar (distinguished from singular), "containing or consisting of more than one," from Old French plurel "more than one" (12c., Modern French pluriel) and directly from Latin pluralis "of or belonging to more than one," from plus (genitive pluris) "more" (see plus). The noun meaning "a plural number" is from late 14c.
late 14c., "inhabited place larger than a hamlet but smaller than a town," from Old French vilage "houses and other buildings in a group" (usually smaller than a town), from Latin villaticum "farmstead" (with outbuildings), noun use of neuter singular of villaticus "having to do with a farmstead or villa," from villa "country house" (from PIE root *weik- (1) "clan"). As an adjective from 1580s. Village idiot is recorded from 1825. Related: Villager (1560s).