as its been established, i genuinely think the painting lie only worked on mike because will is such a terrible liar and he knows this but will genuinely believed every word he was saying up until he stumbled through "el commissioned it".

its canon that the lie made mike feel so genuinely loved that he used those feelings for his speech, so i dont doubt he wasnt caught up in his feelings as it happened bc hes self-absorbed like that. but even then i dont think he fully just trusted that will would never lie to him (as he lashed out at him a day or so earlier bc he believed will lied/covered for el), it was because we know will wasnt lying about what he was saying.

will byers didnt just flat out lie. he sprinkled in the lie so mike wouldnt notice it amongst what he was CONFESSING. because the painting lie isnt based off of a lie. its the truth covered up with one.

THAT IS WHY ITS THE CYRANO TROPE. these things are the TRUTH. someone is telling the TRUTH, the MESSENGER is the lie.

that being said, i doubt the painting was ever meant to be a confession (obviously bc it was in the moment). will painted that for him because they werent talking. he has feelings for mike, sure, but he also didnt have his friend. he hasnt for a year. he just wanted to remind him that he is still there. theyre all still a party and not hugging him at the airport crushed his spirit on it. he says it at the rink, they used to be best friends. what happened to it? thats why all the boys are in the painting. its not a cleradin painting. its a PARTY painting. i feel like in fix it fics and stuff no one is utilizing this information. they dont ever have will say any of this come confrontation time. they always have him say something along the lines of "well if i said it was from el it would mean more to you" and ends it there as if the painting was some huge confession of love and not a friendship olive branch.

the thing that makes byler special is that they are best friends first and foremost. romance is a plus after the fact. having will not say why he spent so much time painting for mike is a crime against them. he deserves to say his piece and he deserves have their friendship be precious to him too without the romance overshadowing that. i think its telling that el saying she thinks will's painting about friendship is for a crush when he had no intention of ever confessing to mike about his feelings. so el saw will's devotion to their party as love. which isnt far off.

will genuinely thinks mike is a leader, he thinks that their party is better for having him in it, he thinks mike (who constantly struggles to speak his full emotions) has heart because will is the one who gets the full brunt of mike's emotions (and it used to be the same for mike with will until things got complicated). he deserves to say these things platonically as much as he does romantically. no one knows mike like will, which is why he depicted mike the way he did. no one knows mike's campaigns/love language like will does, which is why he used d&d as a way to show his care.

[you can't make this shit up]

something about Jonathan and Nancy talking on the car roof about Steve commissioning taking Nancy home (duh)

edit. yes, paintinggate is the reason for posting the upper pics! I’m referring to that scene the same way I did here, quoting it

and now this:

watching it now, I literally could hear Mike’s intonations, but I wasn’t sure which scene exactly… then it clicked:

“everyone is so nice here and ive made lots of friends”

The next day

El lied to Mike and then Will lied to Mike ABOUT El and then Mike lied to El because of the lie Will told him and El knew he was lying and they NEVER TALKED ABOUT IT AGAIN

And not one iota of this mess was resolved in any way in S5.

Just the concept of the painting being used as a totem of sorts to track how making changes in the timeline is affecting the future, like Back to the Future (1985):

Or could it signify Will being erased from the timeline or memories? (people slowly forgetting, started with his birthday?)