I watched 5 episodes in a row but I gave these 2 their own entry because they are much better and important episodes.
First up is "heartbreak". Kevin is overjoyed when he finds out his school is going on a field trip to a museum with winnie's school. He tells her the news and she is meh about it while telling him how is she going to sneak on his bus. Kevin devises a plan which he executes to perfection and ends up with winnie on his shoulder on the way to the museum. Madeline took a seat next to kevin but he shoo'd her away before winnie could see. At the museum things get awkward and winnie is noticeably more distant. She wants to spend her time with her group of friends and kevin wants to spend the day as a lone couple. Kevin somehow ends up getting lost by himself when madeline pops up and tries to put the moves on him. He comes close to kissing her when winnie also pops up out of nowhere. Kevin pleads his case but winnie cuts him off with the heartstabber line "Kevin I met someone" and that is all that needs to be said. We are treated to fred savage making his best heartbreak face. He literally just stares at her while trying not to cry. She gets on her bus and kevin returns to his seat where he finds the ring he gave to winnie. He realizes he lost "the girl next door" and the camera pans out where we see both buses driving parallel to each other. One takes a right turn while the other continues straight. This is a pretty good metaphor for heartbreak.
You must watch the ending at least once which you can see here. It will make something get in your eye especially with the music.
Denial is the 2nd part and continues where hearbreak left off. Kevin is in denial over the break up like any other boy would be after his 1st gf dumps him. Madeline keeps popping up throughout this episode as a red herring. First when kevin is at his locker and it's just to say hi. 2nd when she tells him she heard the news about winnie. Kevin meets winnie's new love (roger) but he still denies they are broken up. He has enough so he plans a party with paul. It will be at paul's house and he will be sure to invite winnie to make her jealous(which is how us guys react in a breakup). He has no idea how he will make her jealous until madeline pops up again because plot device and kevin invites her as his date. The day of the party comes when kevin realizes paul also invited roger along with winnie. Kevin tries hard to fake how much he is enjoying himself. He has a chat with winnie that goes well until he tells her their "relationship" didn't mean much to him. She is hurt by this and kevin realizes that was a douchebag move of him. Madeline goes to put more moves on him but he tells her to get lost. Kevin goes home to his garage to be alone but he finds jack already there. No words are said, kevin simply cries in jack's arms while he says "I wish I could tell you it gets easier". This line gives him more depth especially when he lets kevin ride his bike to winnie's house to make up. Yes they make up and have a long chat about various things while kevin ends with this quote "Love makes you do funny things. It makes you proud. It makes you sorry.
That night we talked. About life. About our times together. Maybe we
weren't the same two kids we had once been. But some things never
change. Some things last. And even though I didn't know what was going
to happen to us, or where we were going. I just knew I couldn't let her
out of my life.".
These 2 episodes show us how quickly life can change when we are little. It reminds me of myself and my first gf only I was in 7th grade(kevin is in 9th) and it wasn't as painful. I also believe adult kevin is taking some artistic liberties with what actually happened so he can make the story be more dramatic. Kevin has been through a lot in his short life. To play spoiler, he doesn't date madeline even though she makes it obvious lots of times she has a thing for him. Also I don't know what he see's in winnie. She's a passive aggressive girl who rarely holds his hand and confuses him even more
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