1377, "to go about, stroll," later (c.1425) "roll from side to side, trundle," from O.Fr. troller, a hunting term, "wander, to go in quest of game without purpose," from a Gmc. source (cf. O.H.G. trollen "to walk with short steps"), from P.Gmc. *truzlanan. Sense of "sing in a full, rolling voice" (first attested 1575) and that of "fish with a moving line" (1606) are both extended technical applications of the general sense of "roll, trundle," the latter perhaps confused with trail or trawl. Fig. sense of "to draw on as with a moving bait, entice, allure" is from 1565. Meaning "to cruise in search of sexual encounters" is recorded from 1967, originally in homosexual slang.
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