How I think painting will be approached in season 5
Well, it took me a while to finally get around to writing this post, and maybe it's just meaningless words being spewed out, but it's something that's been rattling around inside my head and I need to get it out. I'm not very good at creating theories, but I have my own opinions on some things, and this is one of them.
First of all, we need to remember that (in my opinion) Mike went to California aware of his feelings for Will and that's why I think he was waiting for a sign of reciprocity. In my view, Robin telling Steve about the importance of asking the "right" girl out and the risks involved in initiating a non-heteronormative romantic relationship isn't just about Rovickie.
With that in mind, let's get to what really matters here, which is approach to painting in season 5.
I think there are two paths to take that are great for Byler's development, assuming Mike understood Will's speech as being about his own feelings, not El's. But first, let's get to what I think WILL NOT HAPPEN. I know most people are expecting El's big "what painting?" moment, and as amazing as that idea sounds at first glance, I think it's the most predictable one to do, and we know the Duffers don't like predictability. I mean, no great producer or writer likes doing what they're expected to do, especially in fantasy/sci-fi content.
Most people expect Mike to question El, thank him, or bring up the subject in a private conversation, but I don't think that's going to happen because: a) assuming Mike wanted and expected the painting mentioned in El's letter to be for him, I don't think he'll bring it up after his "fake speech." I mean, what would he say? "Oh, El, thanks for the painting you asked Will to do for me. I really didn't expect it to come from you, but since it did, I guess it's a good reason for us to get together." No. I just don't see it happening like that. And b) If the subject wasn't brought up right after the reunion/speech, it won't be, at least between El and Mike. I mean, if I receive an incredible gift that means so much from my girlfriend, I would immediately bring it up when I see her after she escapes from mad scientists and an army and such.
So I don't think the painting issue will be addressed between El and Mike. I think the window of time for that to happen in a more fluid and coherent way has already passed. Mike and El are officially dating and trying to make things work. There's no reason to drag this out for days, months, etc. I just don't see how.
Now about what I think might happen. We have two paths here, both paved by the knowledge that Mike Wheeler knows he loves Will Byers and expected it to be reciprocal. So, going by the theory that there will be some scenes BEFORE the time jump (because I don't see how they could do the jump without explaining a lot of things that were left open), we have the following theories:
1st: The painting would be brought up in a tense, climactic moment between Mike and Will. Perhaps during an argument or when one of them is dealing with Vecna's attack. But my big bet is Churchgate. Okay, I think it's clear that I'm a big fan of this theory, and I really need to elaborate on it in a post, but in short, I think Mike using the fact that he knew about the painting from the beginning at a moment when Will is vulnerable and/or possessed would be incredible. Something like, "I know what you meant back there in that van, Will, I know it was you, and I know it because I feel that way too," or something like that. And how would Mike know about the painting? Well, besides the fact that I believe he expected reciprocity from Will, we have to consider that Mike Wheeler is quite intelligent in his own right.
I think he was confused when Will supported him in giving the speech to El because he knew what Will was saying in the van was about them, about both of them, about Byler. And he wanted it to be. He was glad it was because he'd been desperately waiting for it. But then the speech came, and the doubts returned, and as Robin said: you have to be sure before asking the right girl/boy out.
Plus, there's the whole end of the world and multidimensional war thing going on, so if the Duffers really want to make the painting pay off and be worthwhile, it has to be at a crucial moment and not in a post or pre-breakup conversation.
2nd: Will would tell Mike about the painting himself. For this to happen, we'd need to see a completely different Will, perhaps the exhausted, angry version we so desperately want, the rebellious Will finally acting, talking, yelling, and punching someone. While I think Mike would be the only one to initiate explicitly romantic action, I don't rule out Will leading him on. Maybe they fight for some reason, a parallel to the rain scene in season three. Will is exhausted and doesn't want to hide anymore, tired of Mike being (or pretending to be) blind. So he just explodes and says something like, "You're so busy trying to be normal that you didn't even notice what was right in front of you, you didn't even notice it was me there, ma van, it was never El" or something like that. I really like this theory, but I confess it's not my favorite, even though I can definitely see it happening.
Regardless of who initiates the conversation/discussion about the painting, one thing I'm certain of: it has to happen between Will and Mike, and only between them. We all know the painting is a highlight of Byler, and bringing El into the picture would only make things a 2.0 version of Mike's speech to El. Great climaxes between a couple are supposed to happen between the couple, not through the intervention or actions of third parties. Besides, how do we know which side of a love triangle is right? Simple: it's the one with the greatest connection, intimacy, and perception of the other. It's the one where things flow most coherently between the two. And bringing El to Byler would be the same as bringing Will to Milkven (as happened in season 4); I just don't see it happening.
Anyway, I hope this made some sense, but I really don't see the painting being approached as anything other than something intimate and crucial between Mike and Will so we can feel its true weight. Or I could just be talking nonsense as usual. Either way, Byler is endgame.
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