Itachi was not clueless. No, he considered himself to be quite intelligent and observant. More so than most people. So how did this escape his notice?

He saw you almost every day, you were partners in the Akatsuki, after all. He could tell who you were just by the sound of your footsteps, you and him were very familiar. Friends? Not exactly, just close acquaintances. Even so, he knew you well. So how did this escape his notice?

Itachi was walking with you through the Akatsuki base, listening to you talk (tuning you out, more like), and out of the corner of his eye he could just barely see the collar of your Akatsuki cloak shift down to reveal bloody bandages wrapped around your neck. Injuries were a normal occurrence, of course, but he wasn't previously aware of that one specifically. Itachi wasn't worried exactly, he knew you could handle yourself, but he wanted to know how that happened. You usually didn't attempt to hide your injuries.

"Why is your neck bleeding?" Itachi asked in his ususal blunt manner, cutting you off mid-sentence. There was no emotion behind his voice, just a cold sort of curiosity.