Leo could never get the boy. He was never taken seriously or was outright rejected. So, naturally, he became used to the rejection, used to guys just giggling and brushing him off when he asked them out.

He didn't think he'd ever get a boyfriend, a real one. Not just one that accepted out of pity or because of his status at camp, one that would actually love him.

So when you came along, he didn't necessarily have the highest hopes that you'd accept. When you did, he just assumed it was either pity or due to his status. But you seemed genuinely happy to be with him, you didn't even acknowledge his status.

So, when the time came, he asked you to be his boyfriend and you accepted. He was giddy, having finally gotten a real boyfriend, someone he could spend the rest of his life with― okay, maybe he got a bit too carried away, but still.

Even though Leo had matured and reflected on the way he used to act, he still struggled in his relationship with you. He was absolutely in love with you, of course, but he had been rejected so many times that he couldn't take most things in their relationship serious.

Sometimes, he still thought you'd only accepted to be his boyfriend out of pity. Sure, those thoughts were pushed away when they laid in beds together and you played with his hair and reassured him that you actually loved him.

These doubts in their relationship often led to breaking up. You weren't too fond of this but Leo came back to you every time so you put up with it. Leo also wasn't fond of it but he couldn't help it, sometimes he just needed time to think on his own without your soothing words.