You just got fired when you were expecting a promotion and a brown nose prick got the job instead. Your GF is more worried about your share of the mortgage than whether or not you might be in a bad place with all of this, and you apparently live in the gloomiest city on the planet. You go to a paradise with the expectation of helping an old friend, catching up, and earning some decent cash when there, then you get it sprung on you that there is no cash, you're expected to be a savior, and you're thousands of miles away from the person with whom you are supposed to be closest.
How do you feel? Charitable? Happy? Or ready to drop kick the next person that puts their problems on you and expects for you to fix them?
If all you want in a game is a MC that is the alpha-dude-stud that simply fucks everything with a cunt and doesn't give two shits about anyone, well, this isn't the game for you. If you are up for a little dab of almost realistic reactions from someone, well, stick around.
But, yes, the dialogue could be better. I think it may be a matter that English is not the first language of the writers so things don't flow as naturally as they would if someone like me were to write the dialogue. Or, maybe they are and they failed English and weren't fond of lit. If they were always playing with computers and searching for porn, that could be the case.