sidle v.

Old English side "flanks of a person, the long part or aspect of anything," from Proto-Germanic *sīdō (source also of Old Saxon sida, Old Norse siða, "flank; side (of meat); coast," Danish side, Swedish sida, Middle Dutch side, Dutch zidje, Old High German sita, German Seite), from adjective *sithas "long" (source of Old English sid "long, broad, spacious," Old Norse siðr "long, hanging down"), from PIE root *se- "long; late" (see soiree).

The "long part of anything" sense is preserved hillside, it also was in 16c.-17c. side-coat "long coat." From 14c. as "lateral half of the body of a slaughtered animal." In reference to bacon, it indicates position relative to the ribs. The meaning "a region, district" is from c. 1400, as in South Side, countryside.

The figurative sense of "position or attitude of a person or set of persons in relation to another" (as in choose sides, side of the story) is recorded by mid-13c. As "an aspect" of anything immaterial (the bright side, etc.), by mid-15c.

The meaning "one of the parties in a transaction" is from late 14c.. The sense of "one of the parties in a sporting contest or game" is from 1690s. The meaning "music on one side of a phonograph record" is attested by 1936. As short for side-dish, by 1848.

The phrase side by side "close together and abreast, placed with sides near together" is recorded from c. 1200. Colloquial on the side "in addition," especially "unacknowledged," with connotations of "illicit, shady," is by 1893.

"in the dark," mid-15c., from dark (n.) + now-obsolete adverbial ending -ling (compare headlong). The verb darkle is a back-formation from 1810 (Moore, who rhymed it with sparkle), assuming the -ing as a present-participle adjective ending.

But having nothing to do with the participial -ing it does not mean growing dark &c.; from the mistaken notion that it is a participle spring both the misuse of the word itself and the spurious verb darkle. [Fowler]

 By the same error, darkling (adj.), "dark, obscure, gloomy" is attested from 1763. The adverb was sometimes darklings, with adverbial genitive -s.