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PS I think we are more offended by his womanizing habits than Blair is. She only gets upset when she actually think he's being threatened ie Chuck develops feelings for a girl.
4. Raina iss likely to be playing Chuck, so if Chuck is developing feelings for Raina, I suspect it's because she's manipuating him.
1. Chuck doesn't come back from Australia with anyone. He meets Raina for the first time 4x12, probably at the same party where he meets her father.
2. Blair has never asked Chuck to change his drinking or his sex habits. As Chuck said at the end of season 2, love is not about expecting a person to be anything other than the way they are. Chuck's bad treatment of Blair should change, but Chuck's other habits are not necessarily relevant here. Blair has not necessarily taken offense at Chuck's womanizing habits. She's more offended that he has trouble facing his feelings.
3. Blair knows that's what Chuck does, and they both agreed as adults that they would separate, and she doesn't expect him to wait for her. In their relationship, loving each other is not related to being faithful to each other right now. They love each other anyway.
I think Lilly knows why and how Ben is in jail.