1520s, "to look obliquely" (since 18c. usually implying a lustful, wolfish, malicious intent), probably from Middle English noun ler "cheek," from Old English hleor "the cheek, the face," from Proto-Germanic *hleuza- "near the ear," from *hleuso- "ear," from PIE root *kleu- "to hear." If so, the notion is probably of "looking askance" (compare the figurative development of cheek). Related: Leered; leering.
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