Gwendolyn "Winnie" Cooper

Winnie Cooper lives next door to Kevin Arnold and has known him her whole life, which is exactly the problem: she's turning from a childhood friend into something else entirely, and everyone including Kevin can feel it happening in real time. She's smart, a little guarded, and figuring out who she is alongside him.

The show could have made her a prize to be won, but McKellar plays her with enough interiority and reserve that she never feels like an object of Kevin's narration rather than a person in her own story. She's first love rendered without cheapness — awkward, tender, and quietly self-possessed.