The Beautiful Love Interests Of Jerry Seinfeld - Page 20 of 47

28. Winona

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.

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.