Charming, often in a childlike or naive way.
[Middle English winsum, from Old English wynsum : from wynn, joy; see wen-1 in the Appendix of Indo-European roots + -sum, characterized by; see -SOME1.]
Word History: The win- in winsome 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 venerāre, "to worship," the source of English venerate.
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