askew adv.

prefix or inseparable particle, a conglomerate of various Germanic and Latin elements.

In words derived from Old English, it commonly represents Old English an "on, in, into" (see on (prep.)), as in alive, above, asleep, aback, abroad, afoot, ashore, ahead, abed, aside, obsolete arank "in rank and file," etc., forming adjectives and adverbs from nouns, with the notion "in, at; engaged in." In this use it is identical to a (2).

It also can represent Middle English of (prep.) "off, from," as in anew, afresh, akin, abreast. Or it can be a reduced form of the Old English past participle prefix ge-, as in aware.

Or it can be the Old English intensive a-, originally ar- (cognate with German er- and probably implying originally "motion away from"), as in abide, arise, awake, ashamed, marking a verb as momentary, a single event. Such words sometimes were refashioned in early modern English as though the prefix were Latin (accursed, allay, affright are examples).

In words from Romanic languages, often it represents reduced forms of Latin ad "to, toward; for" (see ad-), or ab "from, away, off" (see ab-); both of which by about 7c. had been reduced to a in the ancestor of Old French. In a few cases it represents Latin ex.

[I]t naturally happened that all these a- prefixes were at length confusedly lumped together in idea, and the resultant a- looked upon as vaguely intensive, rhetorical, euphonic, or even archaic, and wholly otiose. [OED]

c. 1400, "turn aside, take an oblique course, run obliquely or at an angle," also "escape," intransitive senses now archaic or obsolete, from Old North French eskiuer "shy away from, avoid," Old French eschiver (see eschew; also compare shy (adj.)).

The transitive sense of "turn (something) aside, give oblique direction to" is attested from 1570s. The meaning "depict unfairly" is recorded by 1872, on notion of being "give oblique direction to," hence "to distort, to make slant"(compare bias, also an image of obliqueness). The statistical sense dates from 1929. Related: Skewed; skewing.

The adjectival meaning "slanting, turned to one side" is recorded from c. 1600, from the verb; the noun meaning "a slant, a deviation" is attested by 1680s.

1520s, "sideways, asquint, out of the corner of the eye," of obscure origin. OED has separate listings for askance and obsolete Middle English askance(s) and no indication of a connection, but Barnhart and others derive the newer word from the older one. The Middle English word, recorded early 14c. as ase quances and found later in Chaucer, meant "in such a way that; even as; as if;" and as an adverb "insincerely, deceptively." It has been analyzed as a compound of as and Old French quanses (pronounced "kanses") "how if," from Latin quam "how" + si "if."

The E[nglish] as is, accordingly, redundant, and merely added by way of partial explanation. The M.E. askances means "as if" in other passages, but here means, "as if it were," i.e. "possibly," "perhaps"; as said above. Sometimes the final s is dropped .... [Walter W. Skeat, glossary to Chaucer's "Man of Law's Tale," 1894]

Also see discussion in Leo Spitzer, "Anglo-French Etymologies," Philological Quarterly 24.23 (1945), and see OED entry for askance (adv.) for discussion of the mysterious ask- word cluster in English. Other guesses about the origin of askance include Old French a escone, from past participle of a word for "hidden;" Italian a scancio "obliquely, slantingly;" or that it is a cognate of askew.