Bronwen has some points to make about your lack of appreciation of Winnie Cooper.
Or, rather, the idea of [Winnie Cooper]. Details about Winnie’s life, like things she might say that aren’t sound bites about their relationship, are often left by the wayside when episodes end, so that future Kevin can learn a valuable lesson about love. Winnie Cooper is a device of convenience. She’s a constant foil to Kevin’s hair-brained schemes, or the person who eggs him on when he’s being a wet blanket — like the time his friends want to hit up a dive bar in the hopes the Rolling Stones will show up. She has her own little acoustic guitar solo that plays when she enters and gives Kevin googly eyes. It’s like she’s a fictional girlfriend whom future Kevin Arnold is inventing for the sake of telling a compelling story. At the beginning of the show, it worked wonders; but by the end, given that Winnie showed very few signs of making Kevin a better person or demonstrating much of a personality of her own, I started to wonder what Kevin saw in her, especially given the myriad other women who cycled into his life and really shook things up.
Winnie Cooper’s motivations and feelings are not meant to be fully understood by either Kevin Arnold or by the audience. At multiple points in the show, Winnie flatly refuses to explain what she thinks or feels to Kevin.
The most crucial point that stands out to me is, of course, from “The Accident.” The episode in which everything happens. So, Winnie has these new friends and goes to the roller rink with them while wearing that fabulous tan leather jacket. And Kevin SHOWS UP UNINVITED to the skating and then can’t even hold his own in crack the whip. Then, per transcript, the following exchange:
WINNIE: Hi Kevin!
KEVIN: How ya doing?
WINNIE: Me? Fine.
KEVIN: I… see that you have some new friends.
WINNIE: Yeah, they’re really nice guys.
KEVIN: Well, Winnie it’s just that when we talked yesterday—
KEVIN: You said—
WINNIE: I really don’t think that’s any of your business Kevin.
JUNIOR: Hey Winnie! Come on, we’re doing a whip.
WINNIE: I’ll be right there!
NARRATOR: I couldn’t understand it. [WINNIE skates away.] What was going on with this girl?
KEVIN: [skating to her] Winnie? Is something wrong?
JUNIOR: [to line of skaters] Okay, get ready!
WINNIE: [to KEVIN] Don’t be silly; everything’s fine.
KEVIN: Yeah, but—
WINNIE: Kevin, I told you I don’t want to talk about it anymore.
KEVIN: Well, I…
[WINNIE joins line.]
NARRATOR: And that’s when I knew: something was wrong.
JUNIOR: All right, let’s go.
NARRATOR: Winnie Cooper was out of control.
Yes, that’s right, Winnie was out of control because she wanted to date a junior. Oh Kevin. So, of course, what happens next is that the junior crashes the car Winnie’s in and she breaks her arm or something. So Kevin climbs up the tree outside her house, Bob Seger has got tonite, and Kevin mimes I love you and Winnie mimes it back. And Kevin, being a dip, interprets this as Winnie being in love with him. No, Kevin, no. She does love you, but she also wants to date hot dudes.
Winnie isn’t merely a foil for Kevin. She’s a girl with agency. And she’s not always thinking what he’s thinking or doing what he wants. The whole point is that Kevin fails to connect to Winnie as more than an idea. The show frequently shows Kevin interpreting other people living their lives as obstacles to Kevin’s perfect order and plans. Winnie’s no different from how Kevin interacts with Paul in this respect, really. Kevin’s own immaturity keeps getting in the way.
Don’t get me started on how he followed her across the country and got her fired in the series finale.
Also, I think there’s totally an argument to be made for the audience view into The Wonder Years being just Daniel Stern’s recollections and not actually how the events “really” happened.