Top 10 Best Kevin & Winnie Moments on The Wonder Years

Growing up, Winnie was always the girl across the street in Kevin’s eyes. His perception is forever changed when Kevin learns that her family is moving. While they aren’t leaving town altogether, four miles can still put a serious strain on a relationship, especially for two kids who can’t drive. What’s worse, Winnie won’t be attending the same school as Kevin next semester. While Kevin wishes to make the relationship work, Winnie feels it would be better to rip the Band-Aid off. The two rekindle their feelings after Winnie reclaims the ring that Kevin got for her, but this still marks the end of an era. Kevin must adapt to not having Winnie as a neighbor, altering their relationship and how he views the world.

After his ex Becky spreads some gossip, Kevin rushes to Winnie to do damage control. He seemingly dodges a bullet when Winnie gets a stomach virus. Kevin sees this as an opportunity to get closer, taking care of Winnie every day after school. The jokes that Kevin made behind his classmates’ backs soon come back to haunt him, however. Karma rears its head again when Kevin falls ill, but he takes some solace in knowing that Winnie never learned the truth. Well, that’s what he initially thinks. When Winnie shows up to return the favor, she reveals that the gossip did make it back to her. This leads to one of their funniest fights as Winnie gives Kevin a taste of his own medicine.

Although we usually skip clip shows, the Season 5 finale is an essential watch. The episode provides several highlights from Winnie and Kevin’s romance, as well as some of Kevin’s other relationships. While it’s nice seeing these moments compiled, the ending solidifies the episode as more than a recap. Spending the night two tables apart after a flirtation with a waitress, Kevin confronts an irritated Winnie. Kevin still has a lot to learn about love and life, but he knows that Winnie is the only girl he’s ever cared about. This is all it takes for Winnie to forgive him with a kiss that brings back more memories. Their relationship has been full of highs and lows, but this moment definitely falls under the latter.

Kevin and Winnie officially start dating in Season 3, but their relationship can still feel like a riddle with no answer. Invited to a make-out party, the couple becomes increasingly nervous when they’re picked for seven minutes in heaven. Winnie flees without a smooch, leaving Kevin to think that their relationship has ended before it even started. Matters take another unexpected turn when Winnie comes to Kevin’s window that night, leading him to a bridge. Calling Kevin her boyfriend, Winnie reveals that she wanted to kiss him, just not under such uncomfortable circumstances. Finally alone, the two share a romantic moment that captures both the innocence and complexity of young love. Sometimes all of your questions can be answered with a simple kiss.

Being the show’s protagonist and narrator, Kevin is used to being the center of attention. When Winnie lands the lead role in a play, Kevin becomes just another member of the crew. Not taking the show very seriously, Kevin has an epiphany when he shines the spotlight on Winnie. Aside from struggling to remember her lines, Winnie feels pressured knowing that her father is in the audience following her parents’ separation. By holding the light on Winnie, Kevin feels as if he’s giving her the confidence to go on. Winnie delivers a powerful performance, moving Kevin to tears and her parents closer together. He may not be the star, but Kevin finds that he can make a difference even when working behind the scenes.

After breaking up the previous season, Kevin and Winnie begin to find their way back to each other under unlikely circumstances. Kevin asks Winnie to introduce him to a girl named Inga while Winnie asks Kevin to set her up with ​​Matt. This blows up in their faces when they wind up on a double date. Instead of getting closer to their new love interests, old feelings resurface. After Inga and Matt click, Winnie and Kevin are left on the dance floor. Their frustration turns to affection, drawing them to the car for a “talk.” What ensues finds a perfect balance between romantic and awkward, as the two kiss on the eyes. Their aim is off, but they’re back on the right path.

From the first episode, “The Wonder Years” has always been about change. Entering Junior High, Kevin starts to see Winnie as more than just a friend. The two kids also start to see that the world isn’t as innocent as they once thought when Winnie’s brother dies in Vietnam. Overcome with grief and confusion, Kevin and Winnie find each other in the woods. As Kevin wraps Winnie in his jacket, the two share the first of many kisses. It was the first kiss for actors Fred Savage and Danica McKellar as well. This ending sets an appropriate tone for the series. It doesn’t shy away from harsh reality, but it also captures both the wonder of youth and the nostalgia we all get looking back.

After telling Winnie that he knows that she’s “crazy about” him, Kevin doesn’t get the response that he expects. Does he ever? Kevin spends Valentine’s Day trying to talk to Winnie, leading to a hilarious misunderstanding with Becky. Kevin survives Becky’s wrath, but his heart is left more broken than ever. After a long day of mix-ups and mixed singles, Kevin outright tells Winnie how he feels. He likes her and, to Kevin’s delight, Winnie likes him too. Walking home together, the two take the first steps towards becoming a full-fledged couple. The sweet moment is capped off with Fred Savage’s little brother Ben playing Cupid. We like to think that Cory Matthews is taking notes for his relationship with Topanga.

In the series finale, a feuding Kevin and Winnie seek shelter in a barn during a storm. This tender moment is something of a goodbye for the couple, who know deep down that their lives are headed in different directions. At the same time, it might mark a first for them. Although it’s left ambiguous if the two went all the way, it’s made clear that Kevin and Winnie don’t end up together. While this didn’t please some fans, it remains faithful to the show’s overarching theme: The end of their romance signifies the end of the titular wonder years, but the separate journeys they take bring them both something special. Even when they part ways, Kevin and Winnie keep their childhood friendship alive.

Between breaking up and getting back together, a more conflicted than usual Winnie tells Kevin that she wants to just forget about the past three years. It takes an accident to put things into perspective. Hearing about the car crash, Kevin rushes to Winnie’s house, waiting outside all day to see her. When her parents turn Kevin away, he eventually goes to her bedroom window. Locking eyes, the two mouth three words in arguably the show’s most touching moment. It’s also the moment that perhaps best sums up Kevin’s relationship with Winnie: complicated yet simple, tear-jerking yet uplifting, and full of unexpected turns. They may not be destined for each other, but Kevin and Winnie will always hold a special place in one another’s hearts.