This is a smaller excerpt of a larger analysis that you can read here i just wanted to make a separate post about this for those who didn't feel like reading through my other obnoxiously long post, haha
Some fans don't really understand why Sasuke did this. But again, when you really look at Sasuke's character, it makes perfect sense.
I believe that Sasuke was able to see himself in Sakura once again (like the acknowledgement moment during the chuunin exams). Sakura, I'm sure, reminded Sasuke of himself and how he always use to chase after Itachi. Just look at the similarities:
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Something else important to know is the difference in language that Itachi uses versus Sasuke. But this can only be known through the original Japanese dialogue. I'll be using an excerpt of a post to best explain this:
or the sake of proper writting, let me give reference in advance regarding what dialogues I will talk about:
"「また今度だ」"Mata kondo da" refers to some dialogues spoken by Itachi to Sasuke in various occations in their past before the Uchiha Clan Downfall. It is often translated as, "Maybe next time." 「
また今度な」"Mata kondo na" refers to a dialogue spoken by Sasuke to Sakura by the time he departed from Konoha (Naruto, 699:15). It is often translated as, "I'll see you soon." Both of dialogues have similarity in「また今度」 mata kondo part, in which literally 「また」mata means 'again' and 「今度」kondomeans 'this time' or depends on the context it can also be 'next time'. Mata kondo in general is used to politely decline an offer. The only difference between two dialogues is that Itachi used 「だ」da, whereas Sasuke used「な」na in the end of sentence. This slight difference, however, makes all the big gap regarding the volume of certainty the speakers indicate in their speeches Particle na in this is dialogue is meant to both the speaker and the addressee. So, it's important to him to make the addresse agree with his opinion, while he basically makes the promise to himself.... Sasuke was never a man with words. However, regarding Sakura, he always conveyed his heart directly. This time, Sasuke made the promise and the way he said it indicated that really meant it. He puts his emotion and feeling into the speech and indicates a strong desire to fulfill the promise. It's important to him to make Sakura agree with his opinion by emphasizing it, while he basically makes the promise to himself."
Please, please, please read the full post about this here (-: It's really amazing! It even goes into the use of particles in the Japanese language, while taking into account Itachi and Sasuke's individual characters.
