I think that there's a decent possibility that Si-eon has been emotionally hurt in the past and his behaviors reflect a sort of defense mechanism. Maybe he was with someone previously, who ultimately only wanted him for his money. If so, I still think that he derived satisfaction from making that person happy, monetarily or otherwise, but that he was ultimately used. As a result, he gets involved only with people who truly need to depend on him for something. He's still getting the satisfaction of "helping" someone, but stands to lose nothing since he's always placing himself in situations where he's always the one giving, not receiving. In actively seeking out only these types of relationships, he can always maintain a better sense of control, and thus, minimize any emotional damage to himself. Yes, this could definitely attract more assholes, as the one guy (writer- forgot his name) pointed out he has a tendency to do so. Dating a guy who turned out to be an ass would be easy to deal with then- satisfy him to satisfy himself, they break up with Si-eon when they've gotten enough from him, and Si-eon still stands to lose nothing but money (which he doesn't care about.)
I think that there's a decent possibility that Si-eon has been emotionally hurt in the past and his behaviors reflect a sort of defense mechanism. Maybe he was with someone previously, who ultimately only wanted him for his money. If so, I still think that he derived satisfaction from making that person happy, monetarily or otherwise, but that he was ultimately used. As a result, he gets involved only with people who truly need to depend on him for something. He's still getting the satisfaction of "helping" someone, but stands to lose nothing since he's always placing himself in situations where he's always the one giving, not receiving. In actively seeking out only these types of relationships, he can always maintain a better sense of control, and thus, minimize any emotional damage to himself. Yes, this could definitely attract more assholes, as the one guy (writer- forgot his name) pointed out he has a tendency to do so. Dating a guy who turned out to be an ass would be easy to deal with then- satisfy him to satisfy himself, they break up with Si-eon when they've gotten enough from him, and Si-eon still stands to lose nothing but money (which he doesn't care about.)