The pet peeve some people have with Sai is that apparently he "guilt-tripped" Sakura into confessing, because otherwise Sakura wouldn't have done it, and thus he is not good for her.
I made a thread here about this very subject a while back and even analyzed things panel by panel, but when you examine Sai's actions throughout this arc, it's as if he's three different people. His personality and justifications for talking to Sakura and Naruto contradict each other multiple times. It's as if someone decided to completely rewrite his characteristics at the last minute after seeing a bunch of fanboy/fangirl backlash towards his initial comments/observations about Naruto loving Sakura and her causing Naruto pain. Immediately in the chapter after he says this, he makes a dumb@ss non-sequitur comment about how everybody relies too much on Naruto as opposed to just Sakura and Shizune joins him by making a moronic unnecessary remark about how Naruto isn't just saving Sasuke because of his promise to Sakura. If memory serves me, I wanna say this took place in chapter 458 or 459. Either way, things go downhill from there.
To be fair, Sai was shown to slowly become more competent at reading people's actions even after his debut (based on a book he was reading). He made some surprisingly accurate observations with respect to how Sakura's fierce behavior towards Naruto was in actuality a testament to how much she cared about him. In a flashback in chapter 457, he's also shown rightfully coming to the conclusion that Naruto loves Sakura in light of how much he smiles towards her all the time. He didn't become a complete retard until the NH/SS got butthurt over his initial comments towards Sakura about Naruto's POAL. Then that entire arc went funhouse mirror all of the sudden.
EDIT: Here's the thread I'm talking about: http://www.narusaku....showtopic=16279
The simplest explanation is "Dramatic tension", a character has to trigger an event even if it means contradicting what they actually know or is out of character for them. Same reason Sasuke went from adamantly defending Naruto from Sakura's insensitive comments about Naruto having no family to hypocritical douchebag shouting at Naruto that he doesn't know what it's like to lose family because he never had one. Or how Kakashi went from calling out Sasuke for obsessing with Revenge to helping Shikamaru out with his because it's apparently it's okay with Shikamaru. Or scenario 2, how knowledge is passed on off screen with no explanation on how it came to specific ears like all supposed classified secrets within Konoha spread like wild fire to all unnamed soldiers within the alliance, I forgot where it was or when it happened, but it did happened apparently.
Point being, I don't care about the reasons they want to point fingers at Sai at all, These yahoos seem to not realize Sakura was under NO OBLIGATION to confess to Naruto in the first place. SHE went with Sai Shikamaru and Kiba to inform Naruto that they are finally going to hunt Sasuke down as a run away ninja as was meant to be. How that scene was SUPPOSED to play out or the reason for it, I don't care anymore, but is its beyond ludicrous that they even think that, not realizing Sakura decided that on her own.
As for how Sai knows Sakura loves Sasuke, actually I think Naruto said right before that Sakura loves Sasuke I believe, and Sai is merely playing off that thinking that it may justify why Sakura was going after Sasuke herself. I don't really feel like wrapping my brain around this drama because it was ill thought out at best with entire mess it became. EVERYONE involved flip flopped on their own damn priorities here and it was basically all because Sasuke is descending into villain status here but his former friends and teacher need to "kiss his behind", make excuses for him and defend him. I said this before, Kishi never got his own priorities straight on whether Sasuke was the typical rival/love-hate bff to Naruto or a villain deuteragonist that is meant to clash with Naruto, and trying to achieve both is where the story fails.
Edited by Phantom_999, 17 July 2021 - 03:41 PM.