Although he didn't know what the problem was, Hitoshi could tell something was wrong. He knew you were hiding some things, he'd had that feeling from the start, and that was not helped by the fact that you refused to tell anyone what your quirk was. He assumed that you were like him then, that your quirk would be seen in a negative light by others. He wasn't like that, but he wouldn't push you. As you two grew closer, he figured you'd tell him your secrets eventually. When you were ready.
Lately though, you had been acting strange. It was like you wanted to tell him something, but backed away every time. It wasn't something that bothered him, but he was definitely worried. What if it was something bad? Maybe he was thinking about it too hard, but he didn't like the idea of something bad happening to you. He could tell you wanted to say something, you just... Couldn't seem to get it out. He had to ask.
He decided to do it one afternoon while you were hanging out in his room. Him sitting on his desk chair, looking at you and deep in thought at the same time.
"Is there anything you've wanted to tell me?" He asked softly. Thinking that it might've sounded harsh, he added to that sentence. "I'll listen, you don't have to worry"