I wouldn't call Barry arrogant, I'd call him dependent. His security, his sense of self, is completely enmeshed in his romantic relationships. In his mind he cannot exist in the absence of someone to support him. When Caroline accuses him of not knowing anything about her, she's entirely right, because to him the details don't matter -- he just needs someone to rely on, and to rely on him. It could be anyone. Which is why he immediately turns to his ex after Caroline leaves him.
Regardless of how you look at it, he's a deeply disturbed man, filled with regret and bitterness.
As for Caroline, she is undoubtedly an arrogant, self centered bitch. So is half the world. I think part of what makes this movie so interesting is that the protagonist, while not despicable, will definitely strike many viewers the wrong way. But the character is complex and if you get past her vanity she actually is quite insightful and understanding.
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Trust me, I'm a doctor.
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