I mean when they are in Chicago, she obviously wasn't in the mood for a date. But later, when they ran into each other on the street, she doesn't want to have lunch even though he's nice to her. And after lunch, she still doesn't want to go out to have dinner with him. Why exactly does she do that? He's nice and good-looking, what is she waiting for?
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Still shopoholic, just wearing a new T-shirt
At the beginning of the movie she has a affair with their boss Jim then at that meeting Jim announces he is going to Chicago to deal with something and to not give any suspicion of their affair Jim asked Rose go with him and she accepts thinking of a romantic weekend (maybe)only for Jim to change his mind by sending Simon in his place.
Then the thing with Maggie and Jim happens so Rose is in no way ready for a relationship, specially someone from the firm she used to work for that's why she is so cold towards Simon until Simon breaks her barriers.
Later we learn Simon has been infatuated with Rose since he stared to work for the firm but Rose never though of him that way...she never thought of anybody in that way with her insecurities and all.
***If you can't laugh then SMILE***
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You call him a douche for that??
I see no issue with him saying that, it's not like he said it in a douchy way like, hey I'm an expert are ordering, much better than you silly pea-brained cow will ever be.