Somehow, I see him in a better light now?
He's putting effort in trying to get his girl, he's not willing to give up and just let it be like how other manga's side characters would.
Cuz if you're with someone for a long time, like per se a childhood friend, one way or another you would develop feelings for him/her (with affections varying between best friends and crush of course). As I said, he has the determination to not give up even when the signs are quite obvious and strive to change it.
I don't know about you guys, but he's doing something that I can't do; which is studying hard for college while also trying to get his girl cuz feck me college is really hard.