Q: I was recently struck by two words that seemed related, but didn’t have an apparent connection in meaning: “leer” and “leery.” I found that interesting. So what’s with these words?
A: As it turns out, “leer” and “leery,” words with negative connotations, began life innocently in Anglo-Saxon times, though their Old English ancestors are now obsolete.
The ultimate source for both is hléor, Old English for the face or countenance of someone, and often used in positive alliterative expressions like “lovely leer,” “lovesome of leer,” or “lily-like leer,” according to the Oxford English Dictionary.
The earliest example in the OED is from a Latin-Old English entry in the Epinal Glossary, believed written in the late 600s: “Frons, hleor.” (Frons is “forehead” or “countenance” in Latin.)
The next Oxford example is from Felix’s Life of Saint Guthlac, an Old English account written for King Ælfwald around 730 to 740 by an East Anglian monk known as Felix:
“he to eorðan on þam anade hleor onhylde” (“he bowed his face to the ground in solitude”).
And here’s a clearly positive Middle English example from the Legend of St. Katherine, written sometime before 1225: “Þi leor is, meiden, lufsum, & ti muð murie” (“Your leer, oh maiden, is lovely, and your mouth pleasant and wise”).
Meanwhile, the noun “leer” took on a new sense in late Old English: the cheek. The earliest example in the OED is from Old English Leechdoms, a collection of Anglo-Saxon medical texts dated around 1000:
“hwylcum weargbræde weaxe on þam nosum oððe on þam hleore” (“boil, warty eruption, wax on nostrils or cheeks”).
The dictionary says the “cheek” sense of the noun “leer” indirectly inspired the verb “leer,” meaning to “look obliquely or askance; to cast side glances. Now only, to look or gaze with a sly, immodest, or malign expression in one’s eye.”
How did the “cheek” sense of the noun lead to the “look askance” sense of the verb? As the OED explains, “the early examples of the verb suit well the explanation ‘to glance over one’s cheek.’ ”
In fact, the earliest Oxford citation for the verb (from John Palsgrave’s Lesclarcissement de la Langue Francoyse, 1530, a French grammar for English speakers) doesn’t have anything to do with glancing sideways over one’s cheek, though it does suggest sneakiness:
“I leare or lere, as a dogge dothe underneth a doore. Je regarde de longue veue.”
But the next example (from William Stevenson’s 1575 comedy, Gammer Gurtons Nedle) does indeed mention a side glance: “By chaunce a syde she leares / And gyb our cat in the milke pan, she spied ouer head and eares.”
The verb “leer,” in turn,” inspired a new sense of the noun “leer” that the OED defines as a “side glance; a look or roll of the eye expressive of slyness, malignity, immodest desire, etc.”
The dictionary’s first citation is from Shakespeare’s The Merry Wives of Windsor, believed written around 1597:
“Shee discourses: shee carues: she giues the leere of inuitation.” (The quote is from the 1623 first folio. The OED notes that the 1602 quarto spells it “lyre.”)
And here’s Milton’s description in Paradise Lost (1667) of the Devil as he looks askance at Adam and Eve in Eden: “Aside the Devil turnd / For envie, yet with jealous leer maligne / Ey’d them askance.”
The adjective “leery” showed up in the 1600s, but the sense you’re asking about (doubtful or suspicious) didn’t appear until the late 1800s, according to OED citations.
The dictionary’s first example is from Artie: A Story of the Streets and Town (1896), a collection of fictional sketches by George Ade: “The old lady’s a little leary of me, but I can win her all right.”
We’ll end with an example from Academic Graffiti (In Memoriam Ogden Nash), a 1971 poem by W. H. Auden.
The Geheimrat in Goethe
Made him all the curter
With Leute who were leery
Of his Colour Theory.
(Geheimrat was Goethe’s title as Privy Councillor; leute means people.)