Going off the train of thought that sasuke ia miserable with sakura and she basically harassed him into submission, how would that affect the way itachi treated and thought of her? Also assuming he was some how alive or reanimated to see it

[[ If Itachi was alive, I don’t think it’d ever happen. (Sasuke and Sakura getting together, that is.) 

Part of why Sasuke was able to be harassed into eventually giving up and accepting a relationship is because he’s isolated from people who would help back him up or demand he be given his space. Taka isn’t traveling with him, Itachi is gone, etc. And if we’re going to believe that Karin is aiding Sakura (as the whole timeline during the pregnancy is unclear), Karin is actively working against Sasuke being able to say no. In Sasuke’s novel, Karin makes comments about Sakura not having anything of Sasuke to remember him by in his absence, and knows she has feelings for him (which is why she gets her the copy of the team photo). 

If you introduced Itachi into the situation, that by itself would just help Sasuke’s self esteem by loads. He would prioritize Itachi and traveling with him,and would definitely not be as susceptible to Sakura’s stalking/harassment simply because he’s got his brother to think about. 

If Itachi could see it was at a level that it was actively interfering with Sasuke’s life and it was crystal clear Sasuke did not want the attention, he would try to coax her to go home, gently.

Itach’s the kind of person who would think it was admirable that Sakura and Naruto never gave up on Sasuke, no matter what he did. He does think this for a very long time. But since this situation is post Edo-Tensei and post-war, Itachi would eventually realize that Sasuke can choose who he is and isn’t friends with, and that just because Sakura loves him, she isn’t owed any of his time or attention (just like Itachi realized just because he did what he did to protect Sasuke, it doesn’t mean he’s owed an ounce of Sasuke’s forgiveness or time.) That’s a very important lesson for Itachi to learn, not just for how he interacts with Sasuke, but for how he sees others interacting with Sasuke.

He would never  be mean or cruel about it. But once Sasuke’s firm on not wanting Sakura’s attention, Itachi would act as his backup so Sasuke can’t be cornered into it. He still thinks it’s nice Sakura has feelings for him, but the nicest thing Sakura can do for Sasuke is actually wait. Maybe one day he’ll return her feelings, Itachi wouldn’t mind, as long as it was purely Sasuke’s decision without any pressure put on him. Maybe he won’t! That’s not Itachi’s decision to make. It’s up to Sasuke. 

But– if you mean being reanimated long after they were together and had Sarada, it’d be too late.

By this time there’s nothing he can really observe that would make him act. It’s already happened, and unless something drastic happens, he really has no reason to assume that Sakura chased Sasuke into submission. He would just be under the impression that they fell in love and married and had a child, even if it is unfortunate that Sasuke’s work keeps him away from his family for years at a time. Without Sakura’s behavior during that blank period to go off of, he just thinks that Sakura’s love for him paid off and that what they have is good. This is just something that can’t be helped without drastic intervention. ]]

Happy birthday to Itachi. Iruka has taken the day off—even if it’s only because it is not a school day—and he is going to spoil him with a carefully moderated excess of sweets and a not-so-carefully moderated excess of kisses. Pancakes (with fruit and eggs) for breakfast, dango after lunch, and a cake for dessert after dinner.

He cries. First thing in the morning.

Itachi hasn’t celebrated a birthday in years. Even when his family was whole, it was just simply something he ignored. Were it not for the date on his shinobi registration, its proximity to that event, and Sasuke’s own birthday, he would’ve completely forgotten it existed.

But it’s a good cry, especially when he notes his brain doesn’t immediately try to tell him the effort is undeserved. 

Iruka gets sloppy kisses, that taste like just a little bit too much syrup in the morning, dragging on through the day.

I’ve always wondered, do you think if he could Itachi would have wanted to love? As you surmise, most characters are heterosexual and I’ve always wondered, what kind of woman Itachi would have gone for if he had the choice. Btw your blog is what keeps me going even with my mental health issues. It sucks but I feel better whenever I go through ur blog.

[[ Aww, I’m glad you like my blog. I hope things go better for you!! 

“Having the choice” is odd wording because Itachi himself kind of shits all over this. He has other priorities and romance is not at the forefront so really the only kind of woman he’d end up with is someone who’s already close to him. Closer than any other women is, anyways. It’d probably still be Izumi.  

Personally, I like women for him that don’t just let him do whatever he wants and will call him out on his weird behaviors, but Izumi is good for him too– in that he wishes to protect her and she doesn’t really get out there. That sounds weird but it works, there’d be little to no conflict in this relationship. ]]

It’s been mentioned before that Itachi’s voice actor could tell Itachi cared about Sasuke because of the hotel corridor scene. I thought Itachi’s behavior was convincing enough there. He much later tells Sasuke he wants his sharingan, that that was his spare pair. So going out of his way to invest in Sasuke’s development and his sharingan’s development makes sense even if he were a villain for real, so he’d get a powerful pair of sharingan out of it, or Mangekyou.

[[ He meant caring about Sasuke in a positive way– Granted both what you mentioned and what Itachi still did does involve manipulation but Crispin could tell he actually loved him, not saw him as a pair of eyes to water until they were ripe. ]]

What behaviors/personality traits are OOC for Itachi?

[[ As a general rule…

Overt Aggression, Quick to Anger, Violence as the First Option, Eager to/Willing to Kill over small infractions, any true belief that he’s dominant/better than people (especially if you add due to Uchiha heritage). 

It’s one thing to be honest about his acting in Akatsuki– that’s fine, he was putting up an act, but when you’re writing Itachi outside of that or before that you can’t just make him some blood-hungry trigger happy person. He isn’t like that. 

Also, any Itachi that acts (outside of Akatsuki again) as if Sasuke doesn’t exist or Sasuke is a burden. He died for Sasuke, his whole plan was with Sasuke in mind. You can’t just make him act like Sasuke’s some annoying sibling he’d rather get rid of. ]]