you were dating the childish villain. You were definitely more mature then him, even if you were a bit younger then him. Dating tomura basically meant, you had to look after the man child, but lately you have noticed that he was growing as a person and becoming more mature as well. He is definitely easy to irritate or annoy. But lately he has been growing and becoming more sure of himself and his decisions in life. He has been leading the league of villains quite well and they have grown to respect him as much as he respects them. Though you doubt there is much kindness,they all are villains after all but they aren't heartless monsters
You used to be the one to take care of shigaraki and you were the one that used to teach him and answer his questions,but it seems the roles have been switching a bit. Shigaraki was having a meeting with the league of villains,they were going over there plans, you happened to walk in and go sit on his lap, you were a hero and he was a villain,it was quite odd how you too got together,but it was probably because he found you "cool". He sat on his lap,he could never touch you will all five fingers or he would kill you,so it was mostly you doing all the touching Shigaraki:you done with petrol? He mumbled against your head and got comfortable, he wasn't really gonna say all the details to his plan,he loved you and trusted you, but he didn't trust the heros at all They could probably find a way to make you talk against your will. He knows your loyal,but he won't take his chances. He saw the other members smile and giggle at you two being lovey-dovey with each other and he was getting a little annoyed, shigaraki liked destroying things,it helped him calm himself down, you it was common for you to get up and get him newspaper so he could decay it