During Season 4, Winnie's family moved a few miles away which sent Winnie to a new school and put her and Kevin's relationship to the test. During a field trip that both schools attended, Winnie revealed to Kevin that she has a new love interest and dumped him. What a great field trip! Before climbing aboard the bus for the sad ride back to his school, Kevin finds the ring he once purchased for Winnie sitting all by its lonesome. Seeing it made the uncomfortable title of "Winnie's ex" a reality.
An episode later, still in denial over his breakup, Kevin convinces his best friend Paul Pfeiffer to host a party in hopes of wooing back Winnie. Paul reluctantly agrees. Winnie and her new boyfriend attend Paul's shindig as does Kevin and his date Madeline (who has flirted with Kevin throughout Season 4). At the party, Kevin works overtime to convince Winnie that he's doing just fine, thank you very much, but no one is buying it. Not Paul, not Madeline, and definitely not Winnie. He eventually puts himself in a timeout and adjourns to the nearby laundry room in Paul's basement when Winnie enters. In an effort to melt the ice, she tells Kevin she needs him to be her friend. Feeling jaded, Kevin tells Winnie he's not her friend and lashes out at her...all the while The Stylistics' "You Are Everything" further paints the picture throughout the scene. After Winnie leaves in tears, Kevin goes home where he finds his dad in the garage. In a tender moment that hits too close to home, Kevin breaks down in front of his usually stoic dad, Jack. Not mincing words, Jack says, "I wish I could say it gets easier."
The episode concludes on Winnie's front porch with a disappointing conclusion where Kevin went to apologize. All the emotion from the previous scene completely drained from the episode when Winnie easily accepted Kevin's apology. Kevin's inner-monologue reveals that his and Winnie's relationship has changed and will never be the same. The narrator ends by saying, "Maybe we weren't the same two kids we'd once been...and even though I didn't know what was gonna happen to us...I just knew I couldn't let her out of my life."
Some things last. And even though I didn't know what was gonna happen to us or where we were going I just knew I couldn't let her out of my life. Read more: https://www.springfieldspringfield.co.uk/view_episode_scripts.php?tv-show=the-wonder-years&episode=s04e12