Etymology: Middle English winsum, from Old English wynsum, from wynn joy; akin to Old High German wunna joy, Latin venus desire — more at win
Date: before 12th century
— win·some·ly adverb
— win·some·ness noun
Charming, often in a childlike or naive way.
Word History: Winsome people easily win friends, so it is not surprising that winsome and win have a common root. Their shared element win- comes from the Indo-European root *wen-, meaning "to desire, strive for," and has a number of descendants in the Germanic languages. One was the prehistoric Germanic noun *wini- meaning "friend" (literally, "one who desires or loves" someone else), which became wine in Old English and is preserved in such names as Winfred, "friend of peace," and Edwin, "friend of (family) possessions." A different form of the root with a different suffix became Old English wynn, "pleasure, joy," preserved in winsome. Finally, the verb win itself is from this root; its meaning is an extension of the sense "to strive for," namely, "to strive for with success, be victorious." Outside of the Germanic branch of Indo-European, we see the root, for example, in Latin venus or Venus "love, the goddess of love," and the verb venerre, "to worship," the source of English venerate.