Gatsby's expectations of his relationship with Daisy are extremely high, and very unrealistic. In his relationship with Daisy, it seems that all he wants is for the last four years to be completely erased with a simple 'I never loved you' to Tom. He wants to have that same connection and bond that he had with her when they were much younger. Especially in this he is obsessive - he doesn't seem to realise (as the romantically obsessed often are) that his dream is just that, and that reality is quite nearly impossible.
It seems as if he is yearning for some indefinable quality that they shared together - for her to be able to 'understand' and to repeat the past with him. His reminiscing with Nick shows how idealised his image of his romance with Daisy has become: 'she blossomed for him like a flower'; and even the description of an idyllic summers night shows just how unrealistic his expectations are. Nick recognises this, yet at the same time there is the sense that what Gatsby is saying isn't completely false and there is some reality hidden under Gatsby's illusion of Daisy ('I was reminded of something...uncommunicable forever').
In pages 105-107, we begin to really get a glimpse of how obsessed Gatsby really is. Ther
Nick is also right when he says that Tom and Daisy 'retreated into their vast carelessness'. The carelessness that is visible in Tom and Daisy is visible in most wealthy people, and by saying that Nick is demonstrating that no matter what mess they make their wealth and other wealthy people will protect them. Then people like Nick have to step in and sort everything out.
Another example of their carelessness is how Daisy treats her daughter. The daughter has a nanny, and never sees her mother. Yet whenever she feels like it, Daisy calls for her daughter to be put on display as if Daisy is saying 'look what great possession I have' (in her daughter). She even introduces her daughter to the man that she's having an affair with - again displaying her vast carelessness to both Gatsby and Pamela.
e really is the sense felt that Gatsby has gone to all of this effort solely for Daisy, and he falls into depression upon seeing just how much things have changed between them ('I feel far away from her...It's hard to make her understand'). He also feels depressed on meeting Tom properly, and on seeing how far apart their social crowds still are (even after all his effort) - the cold hard reality is almost sinking in. However after this his hope and optimism returns (his 'r
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