I have a theory. In the books, when Georgie met Pennywise, Pennywise offered a balloon to Georgie and Georgie refused to take it saying he wasn't allowed to accept gifts from strangers. Pennywise outsmarted him by introducing itself and renewed its offer. But that wasn't enough to bring down the little boy's warriness. Georgie then asked if the ballon could float. Pennywise basically answered "yes" and Georgie, convinced, tried to reach to it, falling into Pennywise's trap. Since then, Pennywise used that same trick, saying "you'll float too" to lure other kids, eventhough it was only Georgie's hobby.
So I started to wonder why. It is a clever creature, a smart predator. It knows what secrets you hide and what kind of fear you have. It wouldn't use uneffective arguments to convince you to trust it. Unless you're really into paper boats like Georgie was, "you'll float too" isn't quite an appealing promise. So I thought maybe Pennywise's powers are under some kind of rule it can't resist, like "If it works once, it always works". We know that Pennywise’s powers depend on how much you believe in it. It's all a matter of belief and faith. And we know this mechanic can backfire on it, since the Losers managed to kill it that way. But maybe Pennywise is also a subject to this rule. If it belives it's powers work a certain way, maybe they do. That's why it uses "you'll float too" as a way to lure its prey. Because it worked once.
Now here's the main part of this theory:
When Beverly discovers Ben’s postcard in her backpack, we can see a book on her desk: The Frog Prince. As we all know this is a story about how the girl breaks the prince’s curse by kissing him. True love wins, basically. If Beverly read this story maybe she belived it too. Let’s not forget she’s only eleven at the time. And maybe that’s why she tried to discover her secret admirer’s identity. Because they were the first person to genuienly like her. A pure and kind love. They cherished her, she could tell so. It was the kind of love she read about on her fairytale books. A poetic and beautiful love, strong enough to break curses.
Then, when Pennywise managed to capture her and showed her the dead lights, she was suddenly the cursed one, hypnotised and flotting in the air, trapped in her own head. It was a real magic curse. The kind she read about. The kind only a true love kiss would break. That’s why she knew, when Ben’s kiss successfuly broke the spell, he was the secret admirer.
As she believed true love could save her, she implemented a new rule on Pennywise's powers. True love breaks curses.
Likewise, in Chapter 2, it’s Richie’s turn to be cursed. And Eddie is the one who saves him. Now, following my theory on how Pennywise's powers work, breaking Richie's curse would have followed the same logic as Beverly's. True love. Since true love worked once, it will always work. Because 11-year-old-Beverly believed so. Meaning maybe, just maybe, Richie's feelings for Eddie were reciprocated, or would have been if Eddie had survive.
Bonus: Bill might have manage to save Beverly too if he had tried, since he was sincerly in love with her too at the time. But we know Pennywise’s powers transend time thanks to Bev’s vision. We also know Ben is the one Beverly chose in the end. So destiny might have been at work here.
Feel free to share your thoughts on this. I know it’s a bit sketchy but I hope I managed to convey the idea.
(I didn't finish to read the books yet. So maybe there are counter arguments in there. In the mean time, I kind of like this idea and I think it fits the moral of the story: You can accomplish anything if you believe in it hard enough.)
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