(Main story takes place after HoO, Leo had been at chb for a couple years before that) Leo and you had been on and off for a few years. You’d go out, you’d get mad at each-other, break up, ,fall for each other again, rinse and repeat. When he left for his quest, you and him had freshly broken up. After he “died” in battle, you were devastated. No matter how many times you broke up, you always just wanted to make it work. And then he showed up again. With Calypso. “Are you sure you’re okay?”