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It might be a bit of a beaten path, but his own personal journey could be an examination of why he doesn't really let anyone get close, anymore. Some half-arms length contact, mostly using the acquisition of money as a wall to prevent that interpersonal connection from growing too deep. A "friend" to him is someone who will tolerate him long enough to give him money. His attraction to his sunbae as terrifying as it is misguided; he thinks he likes her, but he truly likes the idea of a good relationship with a beautiful woman.
Sorry, kids, I might just be in my melancholy cup.
His childhood friend? Brother, she has no obligation to love you more than she has feelings for you. She had a boyfriend. Or has one. You can be friends. It honestly doesn't seem like you wanted to be friends with her unless she could be a romantic option, which is typical of stories like this. If she ever gets mad at you during this, it's honestly on you for not being able to move past it.
His sister. All we know is that she was bad to him, somehow, so the jury's out, there.
This is starting to feel very self-indulgent. Not to mention that he's a self-proclaimed "gloomy guy." He's doing his best to be aloof and cool about it, but I doubt that he's a true "gloomy guy" in the same way that Uichi is in You are a Four-Left Clover. It feels forced. Annoying. Maybe that's on purpose. I dunno.
Murata: https://i.postimg.cc/440Hj8FY/i.jpg