Though Winnie Cooper would always remain in his heart, he found enough time for romance elsewhere. Were you on Team Winnie? Or did you always wonder why he didn't ditch her and date Madeline Adams instead? We took a look back at the many girls and women in Kevin Arnold's life to see what they were like then and what they look like now. Winnie was wholesome, perhaps bordering on prissy at times. Despite being Kevin's first love and vice versa , they separated after high school and never reunited.
Joe' cartoons. Then: Once a sweet if not overbearing girl, Kevin dated Becky solely to make Winnie jealous and when Becky found out, she turned bitter and vindictive once punching him in the stomach. Now: Crystal is Danica McKellar's real-life sister.
But their love was on the rocks when Kevin started tutoring Denise in poetry. Frank believes this is Kevin's fault. Then: A beautiful dental assistant who makes Kevin uncomfortable when he goes to get a cavity filled.
He asks his dentist that she not work during his appointments because he's so embarrassed. Now: Kershaw has retired from acting and now focuses on a writing career, penning a parental advice column. Then : Kevin goes on a summer vacation with his family and the Pfeiffers but winds up ditching them when he meets Cara, a rebellious local.
They fall in love but after the week is over, Kevin fails to keep in touch. In a subsequent episode, Kevin impulsively returns to find her, but she's upset he never wrote and tells Kevin she has a boyfriend and he should go back home. Then: Madeline was the new girl in high school and fell madly in love with Kevin who was trying to stay faithful to Winnie who was attending a different school.
