"You winsome, you lose some." This awful pun notwithstanding, what does the SAT word "winsome" mean?

Answer Cheerful or lighthearted

From Merriam-Webster:
win·​some | \ ˈwin(t)-səm \
1: generally pleasing and engaging often because of a childlike charm and innocence
a winsome smile
2: CHEERFUL, LIGHTHEARTED

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