Honestly, as much as I loved It: Chapter Two, I still can't take those flashback scenes seriously. The CGI takes me out of it and I can't even watch without feeling a little awkward. Then, I was thinking about like why didn't they just leave the kids how they were? Why couldn't they have written the flashbacks about the next summer?
The summer of 1990 would have been incredibly interesting to know about. Bill and Beverly had already moved away. Richie was the next to go. Pennywise still could have made an impact, but in the form of nightmares due to it being one year later. They haven't forgotten because they're still in Derry. And their tokens? They could have been from the days that they left Derry.
Bill lost his stutter, and he rides around on his bike with a girl that looks awfully a lot like Beverly. His walkie-talkie sits in a box in the attic covered in dust. The girl laughs as they sit and make paper boats together.
Beverly lives with her aunt, and she continues to practice playing the keyboard. Her aunt teaches her to sew as they watch old movies. When replacing the batteries of the keyboard, she comes across a poem stuffed inside the battery compartment.
Richie visits some of his favorite places in Derry before having to go home and throw his bike in the back of a truck, leaving behind his whole life. Of course, he's angry. He's been shutting out everyone since the day his parents told him they're moving out west. He doesn't want to believe it. The arcade scene could still be in the movie, even. And the Paul Bunyan thing. Except this time, Eddie helps him up. They walk together, talking about what it'll be like after Richie is gone. Eddie eventually goes home, and Richie goes to the Kissing Bridge before making his way home and saying goodbye to his friends.
Ben is the next to leave, as his mom lost her job and needs to move back to Nebraska to be with family. He goes back to the library to return a few books he still has checked out where he remembers what happened the year before in the library. We then see him at home taking down all the things in his room about Derry. Mike comes over and asks if he can have them, Ben shrugs and he walks out to his mom's car.
Eddie leaves next, his mom getting really sick and having to move somewhere with better care. Eddie spends the whole day with Stanley and Mike, they go to the movies and see Arachnophobia. The whole time, Eddie tries to hold Stanley's hand because he's scared. Mike looks increasingly worried as he pulls out a book to read. Afterwards, they go to the pharmacy for Eddie to refill his medicine.
Stanley is the last to leave, his parents want to move to New York to be closer to family. He's the most distressed about leaving, walking around to his friends' old houses and seeing some of them sitting empty (he throws rocks at Richie's old house, being mad at him for leaving). He eventually goes to the clubhouse, where he sits in the hammock and cries while wearing that silly shower cap. Mike eventually comes down with Stanley's mom, and they have to pull him away from the clubhouse.
We then see Mike, sitting alone for years and years. He gains a hatred of the town for taking his friends away, for leaving him alone and vulnerable. He sees a Help Wanted sign at the library and goes straight in. He wants a job where he can help people, learn history, be himself.
I honestly just think the next summer would have made an amazing bridge between the two films. We can see the progression of time, we can see change. The kids are older, they are separated from each other. Which would make so much more sense with the context of the second movie. The Losers spend the whole movie separated from each other. By showing them being ripped apart from each other, we can see why A. they don't want to get too attached again and B. why their relationships are so strained. The are basically strangers. Having them together at the Jade of the Orient would help recapture that innocence of childhood friends, of the first movie. We can see them grow and change as kids into teenagers. Richie is taller, he does grow into his looks like Beverly said. Stanley's hair grows darker. Ben starts losing weight. Eddie grows into a mature teenager, a welcome departure from when he was the smallest. Mike matures as well, but develops dark circles under his eyes from the lack of sleep. Because Bill and Beverly left, they relatively look the same.
Plus I can imagine all the jokes Eddie and Richie would have for each other?
"Richie, I refuse to believe you grew an entire fucking foot just because you ate too many vitamins."
"Eddie, your hair isn't straight anymore. Are you trying to tell us something?"
"Can you go get a haircut? Or at least wash your hair, it looks disgusting."
"Big man over here, finally grew some balls after his voice dropped. I really do miss hearing a five-year-old yell at me about some dumbass, made-up disease."
"Remind me again, who got the flu for a week after licking the flagpole?"
"Hey, I earned that ten bucks. Plus, Stanley felt so fucking bad that he cleaned up my puke for that whole week. The look on his face was priceless, I swear he was going to just fucking pass out."