The first time Toshinori met you was in America, working alongside David Shield. David and Toshinori were good friends, but when he was introduced to you, it was basically love at first sight. Whenever he could, Toshinori would always steal glances in your direction whenever you worked together, always finding some excuse to be just a little closer to you. David noticed, and he found it rather amusing.
Toshinori really hit it off with you. Your relationship was easy, a little distant due to his work, but it was comfortable- you never had anything to fight over, and you agreed on almost everything. He couldn't dedicate himself to you fully because of his position, but in the near future, when or if there was some peace for him, he promised you a ring, a future together- like he was going to stay in America with you forever.
But then reality hit. He had to move back to Japan, and for one reason alone. An old enemy of his was making his rounds again- the same man who killed his mentor years ago. This fight was inevitable, and he knew it.
You were already willing to make the move to Japan with him, and for the first time, he hesitated. He was moving higher in the ranks as the days went on, labeled "The Symbol of Peace", and he knew that if AFO, or any villain for that matter, found out about his soft spot for you, he'd be in trouble. Too much trouble. And for that reason alone, he couldn't take you to Japan with him; he couldn't risk your life to live out some fantasy he had been imagining for months. He sought advice from his David, but it seemed like he was at a loss as well, so Toshinori did what he thought was right.
One night, while you were asleep, he snuck out and caught the earliest flight back to Japan, cutting ties with you so suddenly, it felt like abandonment. Completely discarding his phone so you were unable to contact him track him down in the near future. He could have gone about this a different way, but if he did, he knew you'd try to change his mind, and knowing him? He'd give in, and that couldn't happen.
It had been 25 years since he left America. Toshinori endured two fights with AFO, which left him in horrible shape and unable to fight as his "All Might" persona anymore. He had the privilege of passing his quirk down onto his own successor, and in doing so, his successor lead a war against the League of Villains, bringing AFO to an end once and for all. Now, he spends his retirement teaching students at UA High School.
You had moved to Japan recently after getting an acceptance to a teacher position at UA High School. With your past behind you, you looked forward to starting a new life.
As students filed out of the building after dismissal, the staff remaining in their office as Nezu wanted to introduce the new teacher. But the moment you stepped through those doors, Toshinori went cold- memories flooding back like a tsunami. He was unbelievably happy to see you, but at the same time, the skyscraper level guilt came crashing back down onto him.
It was safe to say you weren't so pleased with the reunion either... You gave him the permanent cold shoulder, ignoring him, passing him short, to-the-point noted whenever you needed something from him, making this even more difficult because you were supposed to be working with him- Nezu thought it would be a good idea to partner the two of you up, simply because you were new.
Toshinori tried talking to you outside of school hours, to put the past behind them and start new, or to pick up where you left off, but you made it painfully obvious you weren't interested.
When you refused to talk to him that morning, Toshinori grew irritated. He NEEDED to speak to you about upcoming tests, and you were being difficult.
With a subtle frown, he spoke before thinking- tossing a stack of papers onto your desk with a loud bang, causing Aizawa and Midoriya to pause their conversation and look over at the two of you.
"You're acting like a brat." Toshinori hissed.
That was Aizawa's and Midoriya's cue to leave the office for a while.