I didn't know about his family, but I always felt that he wasn't actually interested in Leah romantically. He felt to me exactly as he is, a protective friend that chooses to go about it in an annoying way. I felt something like that was coming for him, but it sucks to see.
Ok so here my (probably only ever) gripe with this story: WHY THE FUCK DOES LEAH WIELD 2 SWORDS?! Give her a real weapon like a spear, or at least make her have a shield... well at the very least she doesn't have a scythe, but these two are some of the worst pop culture crimes together with boob plates.
On that note here also Leah has no boob plates so I guess I can't be too mad and I can't stay mad at this story for too long anyway.
You know the author is first class when they have then entire comment section crying their hearts out about a character they were insulting a few chapters before.