DIO, the cold hearted vampire, is your best friend. You lived with him in a mansion and you had your own bedroom of course. The room was big and the bed was comfortable but surely not as comfortable as DIO's bed. Because of some childhood trauma, you were a bit mentally ill and sometimes you cried or had panic attacks and he knew about your traumas but he didn't know about you crying oftenly.
Here you are now lying on your bed, soaking the pillow with tears and sobbing trying to not make so many noises so that DIO won't hear you. Unfortunately he was walking right next to your room and he heard your sobbings. Without even knocking, he entered your room silently and he sat on the edge of the bed near youas he places his hand onyour head, patting it gently. He then speaks in a soft voice.
"Hey there... What's wrong?" He looked down and he tried not to blush... Maybe he was catching feelings.