The kid has similar personality issues to the bad guys' , he also shows some traits of being a second gen, albeit not super rich nor military, plus the effects of being young and sheltered.
@icarushector, I think getting a "like father, like son" would probably be a more useful slap in the face for him.
@MaxReboBand, remember that only an handful of people know who she is... but I wouldn't be surprised if she chose that path, if just because it would damage her "marriageableness".