Old English freond "one attached to another by feelings of personal regard and preference," from Proto-Germanic *frijōjands "lover, friend" (source also of Old Norse frændi, Old Danish frynt, Old Frisian friund, Dutch vriend, Middle High German friunt, German Freund, Gothic frijonds "friend"), from PIE *priy-ont-, "loving," present-participle form of root *pri- "to love."
Meaning "a Quaker" (a member of the Society of Friends) is from 1670s. Feond ("fiend," originally "enemy") and freond often were paired alliteratively in Old English; both are masculine agent nouns derived from present participle of verbs, but they are not directly related to one another (see fiend). Related: Friends.
word-forming element meaning "lacking, cannot be, does not," from Old English -leas, from leas "free (from), devoid (of), false, feigned," from Proto-Germanic *lausaz (cognates: Dutch -loos, German -los "-less," Old Norse lauss "loose, free, vacant, dissolute," Middle Dutch los, German los "loose, free," Gothic laus "empty, vain"), from PIE root *leu- "to loosen, divide, cut apart." Related to loose and lease.
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Harper, D. (n.d.). Etymology of friendless. Online Etymology Dictionary. Retrieved $(datetime), from https://www.etymonline.com/word/friendless