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From The Collaborative International Dictionary of English v.0.48:
Winsome \Win"some\, a. [Compar. Winsomer; superl. Winsomest.] [AS. wynsum, fr. wynn joy; akin to OS. wunnia, OHG. wunna, wunni, G. wonne, Goth. wunan to rejoice (in unwunands sad), AS. wunian to dwell. ????. See Win, v. t., Wont, a.] [1913 Webster] 1. Cheerful; merry; gay; light-hearted. [1913 Webster] Misled by ill example, and a winsome nature. --Jeffrey. [1913 Webster] 2. Causing joy or pleasure; gladsome; pleasant. [1913 Webster] Still plotting how their hungry ear That winsome voice again might hear. --Emerson. [1913 Webster]