late 14c., "to go about, stroll," later (early 15c.) "roll from side to side, trundle," from Old French troller, a hunting term, "wander, to go in quest of game without purpose," from a Germanic source (cf. Old High German trollen "to walk with short steps"), from Proto-Germanic *truzlanan.
Sense of "sing in a full, rolling voice" (first attested 1570s) and that of "fish with a moving line" (c.1600) are both extended technical applications of the general sense of "roll, trundle," the latter perhaps confused with trail or trawl. Figurative sense of "to draw on as with a moving bait, entice, allure" is from 1560s. Meaning "to cruise in search of sexual encounters" is recorded from 1967, originally in homosexual slang.