28. Winona
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Actress: Kimberly Guerrero
At one point Jerry starts dating Winona, a very beautiful Native American woman. However, Winona feels offended by Jerry’s perceived insensitivity when he gives Elaine an Indian cigar as a gift.
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Afterward, Jerry then goes above and beyond trying to be “politically correct” around Winona. This goes so far as avoiding any words that could possibly be considered crass or impolite under any circumstance.
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