In one episode after breaking up with Winnie, Kevin comes home to see his dad working in the garage. After trying to say he doesn't want to talk about it, the scene ends with Kevin crying while his dad just hugs him.
"A Very Cutlip Christmas" has the usually tight-fisted and mean-spirited Coach Cutlip playing jolly old Santa Claus at the mall. That alone is worth a mention.
Also when Kevin accidentally lets the secret slip, his schoolmates find it hysterical and go to the mall to heckle Cutlip. But they only see a warm and friendly Santa, never recognising their teacher.
Kevin and Winnie's first kiss in the first episode. He goes to the woods to comfort her after finding out her brother died in Vietnam, and apologizes for insisting he didn't even like her when Wayne was giving him a bad time about it.
Kevin and Winnie finally becoming a couple in the second season, after a year of dancing around each other.